- Competitive influence of carboxylic groups in ionic complex formation of 4-hydroxybenzylidene alkanones with polyamidines
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Interactions of phenolic and carboxylic group containing chromophores (hydroxyarylidene alkanones) with polyamidines were investigated by UV/vis and 1H NMR spectroscopy. Because of the strong basicity of the polyamidines, deprotonation of the c
- Dudkina, Marina M.,Tenkovtsev, Andrey V.,Komber, Hartmut,Haeussier, Liane,Boehme, Frank
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- Biological activity evaluation and action mechanism of 1,4-Pentadien-3-one derivatives containing thiophene sulfonate
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A series of novel 1,4-pentadien-3-one derivatives containing a thiophene sulfonate group were designed, synthesized, and their antibacterial activities were assessed. Antibacterial bioassays indicated that some of the title compounds exerted significant bioactivities against Xanthomonas axonopodis pv. Citri (Xac), Ralstonia solanacearum (Rs) and Xanthomonas oryzae pv. Oryzae (Xoo). Especially for Xac, the value of minimum 50% effective concentration (EC50) of compound 4-((1E,4E)-5-(3-nitrophenyl)-3-oxopenta-1,4-dien-1-yl)phenylthiophene-2-sulfonate (3k) is 11.0 μg/mL, which is significantly superior to bismerthiazol (BT) (51.6 μg/mL) and thiodiazole-copper (TC) (94.7 μg/mL). Meanwhile, the mechanism of action of compound 3k was confirmed by using scanning electron microscopy (SEM). These results suggested that 1,4-pentadien-3-one derivatives containing thiophene sulfonate group may be considered as activators in the design of antibacterial agents.
- Guo, Tao,Xia, Rongjiao,Chen, Mei,Su, Shijun,He, Jun,He, Ming,Wang, Hua,Xue, Wei
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- The synthesis of phycopsisenone, a new phenolic secondary metabolite from the sponge Phycopsis sp.
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A short first total synthesis of phycopsisenone (1) utilizing microwave irradiation-induced aldol condensation and TiCl4-catalyzed reaction of silyl enol ether (3) with acetone as key steps has been achieved in 29.4% overall yield.
- Kad,Singh,Khurana,Singh
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- Synthesis and antiviral activities of novel penta-1,4-diene-3-one oxime derivatives bearing a pyridine moiety
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A series of novel penta-1,4-diene-3-one oxime ether derivatives bearing a pyridine moiety were designed and synthesized, and their antiviral activities against tobacco mosaic virus (TMV) were evaluated. The results of the biological assay indicated that most of the title compounds exhibit good antiviral activities against TMV at 500 μg/mL. In particular, the title compounds 5c, 5j, 5o and 5p showed remarkable curative activities against TMV, with EC50 values of 274.8, 299.2, 251.8 and 287.7 μg/mL, respectively, which were superior to that of ribavirin (379.8 μg/mL). This study indicates that penta-1,4-diene-3-one oxime ether derivatives bearing a pyridine moiety can serve as potential alternative templates in the search for novel, highly efficient, anti-plant viral agents.
- Wang, Xiaobin,Chen, Meihang,Li, Qin,Zhang, Juping,Ruan, Xianghui,Xie, Yan,Xue, Wei
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- Design, synthesis, and antiviral activity of novel purine derivatives containing 1,4-pentadien-3-one moiety
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A series of novel purine derivatives containing 1,4-pentadien-3-one moiety were designed and synthesized. The optimal conditions for the synthesis of the target compounds E1–E25 were as follows: solvent, DMF; catalyst, KOH; temperature, 40?°C; time, 2?h; and molar equivalent of A:D:Catalyst, 1:0.8:1.2. Antiviral bioassays indicated that compounds E1, E3, E5, E7, E18, and E19 showed excellent protection activities, with EC50 values of 188.9, 194.6, 125.2, 134.1, 137.8, and 195.4?μg/mL, respectively, which were better than that of Ningnanmycin (271.2?μg/mL). To the best of our knowledge, this study is the first report on the design, synthesis, and antiviral activity of novel purine derivatives containing 1,4-pentadien-3-one moiety.
- Wu, Fang,Li, Pei,Hu, Deyu,Song, Baoan
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- Preparation of a raspberry ketone precursor in the presence of rare earth oxide catalysts
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The raspberry precursor 4-(4-hydroxyphenyl)-but-3-ene-2-one which afterwards undergoes a catalytic hydrogenation to produce raspberry ketone was synthesized by aldol condensation of acetone and 4-hydroxybenzaldehyde over rare earth oxides as basic catalysts and supported rare earth oxides as acid-base bifunctional catalysts. Thereby, several rare earth metal oxides were tested in their neat form as well as supported on carriers with high surface areas such as alumina, titania, tetragonal zirconia and charcoal. The catalysts were characterized by XRD, BET, NH3/CO2-TPD and pyridine-FTIR. All experiments were carried out batch wise in 75 ml autoclaves adjusting molar ratios of acetone and 4-hydroxybenz-aldehyde from 12:1 to 4:1, temperature range from 80 to 200 °C and autogeneous pressures from 1 to 25 bar. It could also be realized, that titania and alumina are no inert materials, but also highly active catalysts for this reaction. An experimental design program was used to optimize the reaction conditions as well as the conversion and selectivity. In addition the reaction was carried out in a fixed bed plug flow reactor to determine stability and robustness of the catalyst. The quality/contaminations of the starting material have a strong influence on the catalytic performance.
- Hoelderich, Wolfgang F.,Ritzerfeld, Verena
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- Synthesis and antiviral activity of novel 1,4-pentadien-3-one derivatives containing a 1,3,4-thiadiazole moiety
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1,4-Pentadien-3-one derivatives derived from curcumin possess excellent inhibitory activity against plant viruses. On the basis of this finding, a series of novel 1,4-pentadien-3-one derivatives containing a 1,3,4-thiadiazole moiety were designed and synthesized, and their structures confirmed by IR, 1H-NMR, and 13C-NMR spectroscopy and elemental analysis. The antiviral activities of the title compounds were evaluated against tobacco mosaic virus (TMV) and cucumber mosaic virus (CMV) in vivo. The assay results showed that most of compounds had remarkable antiviral activities against TMV and CMV, among which compounds 4b, 4h, 4i, 4k, 4o, and 4q exhibited good curative, protection, and inactivation activity against TMV. Compounds 4h, 4i, 4k, 4l, 4o, and 4q exhibited excellent protection activity against TMV, with EC50 values of 105.01, 254.77, 135.38, 297.40, 248.18, and 129.87 μg/mL, respectively, which were superior to that of ribavirin (457.25 μg/mL). In addition, preliminary SARs indicated that small electron-withdrawing groups on the aromatic ring were favorable for anti-TMV activity. This finding suggests that 1,4-pentadien-3-one derivatives containing a 1,3,4-thiadiazole moiety may be considered as potential lead structures for discovering new antiviral agents.
- Yu, Lu,Gan, Xiuhai,Zhou, Dagui,He, Fangcheng,Zeng, Song,Hu, Deyu
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- Antimicrobial evaluation and action mechanism of pyridinium-decorated 1,4-pentadien-3-one derivatives
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A type of pyridinium-decorated 1,4-pentadien-3-one derivatives possessing flexible alkyls were designed and synthesized by integrating the key scaffolds of pyridinium cations and 1,4-pentadien-3-one skeleton in a single molecular architecture. Antimicrobial bioassays indicated that some of the target molecules exerted considerable bioactivities against six phytopathogenic strains, especially for Xanthomonas oryzae pv. oryzae, the minimal EC50 value can reach to 0.504 μg/mL. A plausible action mechanism for this kind of compounds was proposed and confirmed by employing fluorescent spectroscopy, fluorescence microscopy, and scanning electron microscopy. We anticipated that this finding can promote high-efficient lead compounds discovery in the research of antimicrobial chemotherapy.
- Zhou, Jian,Tao, Qing-Qing,Wang, Pei-Yi,Shao, Wu-Bin,Wu, Zhi-Bing,Li, Zhong,Yang, Song
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- Enzymatic formation of an unnatural methylated triketide by plant type III polyketide synthases
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Octaketide synthase, a novel plant-specific type III polyketide synthase from Aloe arborescens, efficiently accepted (2RS)-methylmalonyl-CoA as a sole substrate to produce 6-ethyl-4-hydroxy-3,5-dimethyl-2-pyrone. On the other hand, a tetraketide-producing chalcone synthase from Scutellaria baicalensis and a diketide-producing benzalacetone synthase from Rheum palmatum also yielded the unnatural methylated C9 triketide pyrone as a single product by sequential decarboxylative condensations of three molecules of (2RS)-methylmalonyl-CoA.
- Abe, Tsuyoshi,Noma, Hisashi,Noguchi, Hiroshi,Abe, Ikuro
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- An efficient Pd@Pro-GO heterogeneous catalyst for the α, β-dehydrogenation of saturated aldehyde and ketones
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An Efficient Pd@Pro-GO heterogeneous catalyst was developed that can promote the α, β-dehydrogenation of saturated aldehyde and ketones in the yield of 73% ? 92% at mild conditions without extra oxidants and additives. Pd@Pro-GO heterogeneous catalyst was synthesized via two steps: firstly, the Pro-GO was obtained by the esterification reaction between graphene oxide (GO) and N-(tert-Butoxycarbonyl)-L-proline (Boc-Pro-OH), followed by removing the protection group tert-Butoxycarbonyl (Boc), which endowed the proline-functionalized GO with both the lewis acid site (COOH) and the bronsted base site (NH), besides, the pyrrolidine of proline also can form imine with aldehydes to activate these substrates; Second, palladium was dispersed on the proline-functionalized GO (Pro-GO) to obtained heterogeneous catalyst Pd@Pro-GO. Mechanistic studies have shown that the Pd@Pro-GO-catalyzed α,β-dehydrogenation of saturated aldehyde and ketones was realized by an improved heterogeneously catalyzed Saegusa oxidation reaction. Based on the obove characteristics, the Pd@Pro-GO will be widely used in the transition metal catalytic field.
- Pan, Gao-Fei,Wang, Zhe,Chang, Yi-Yuan,Hao, Yue,Wang, Yi-Chen,Xing, Rui-Guang
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supporting information
(2021/12/30)
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- Synthesis and antibacterial activity of novel 1,4-pentadien-3-one derivatives bearing a benzothiazole moiety
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In search of novel and efficient pesticides to combat increasingly resistant plant bacteria, in this work, 17 novel benzothiazole decorated penta-1,4-diene-3-one derivatives were designed and synthesized, the structures of all new compounds were systemati
- He, Ming,Sun, Nan,Wang, Yihui,Wu, Yongjun,Xue, Wei,Zhou, Ran
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supporting information
(2021/11/17)
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- Design, green synthesis, antioxidant activity screening, and evaluation of protective effect on cerebral ischemia reperfusion injury of novel monoenone monocarbonyl curcumin analogs
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Antioxidants with high efficacy and low toxicity have the potential to treat cerebral ischemia reperfusion injury (CIRI). Dienone monocarbonyl curcumin analogs (DMCA) capable of overcoming the instability and pharmacokinetic defects of curcumin possess notable antioxidant activity but are found to be significantly toxic. In this study, a novel skeleton of the monoenone monocarbonyl curcumin analogue sAc possessing reduced toxicity and improved stability was designed on the basis of the DMCA skeleton. Moreover, 32 sAc analogs were obtained by applying a green, simple, and economical synthetic method. Multiple sAc analogs with an antioxidant protective effect in PC12 cells were screened using an H2O2-induced oxidative stress damage model, and quantitative evaluation of structure–activity relationship (QSAR) model with regression coefficient of R2 = 0.918921 was built through random forest algorithm (RF). Among these compounds, the optimally active compound sAc15 elicited a potent protective effect on cell growth of PC12 cells by effectively eliminating ROS generation in response to oxidative stress injury by activating the Nrf2/HO-1 antioxidant signaling pathway. In addition, sAc15 exhibited good protection against CIRI in the mice middle cerebral artery occlusion (MCAO) model. In this paper, we provide a novel class of antioxidants and a potential compound for stroke treatment.
- He, Wenfei,Wang, Jingsong,Jin, Qiling,Zhang, Jiafeng,Liu, Yugang,Jin, Zewu,Wang, Hua,Hu, Linya,Zhu, Lu,Shen, Mengya,Huang, Lili,Huang, Shengwei,Li, Wulan,Zhuge, Qichuan,Wu, Jianzhang
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- Novel penta-1,4-diene-3-one derivatives containing quinazoline and oxime ether fragments: Design, synthesis and bioactivity
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A series of novel penta-1,4-diene-3-one derivatives containing quinazoline and oxime ether moieties were designed and synthesized. Their anticancer activities were evaluated by MTT assay, the results showed that most compounds exhibited extremely inhibitory effects against hepatoma SMMC-7721 cells. In particular, compounds Q2 and Q8 displayed the more potent inhibitory activity with IC50 values of 0.64 and 0.63 μM, which were better than that of gemcitabine (1.40 μM). Further mechanism studies indicated that compounds Q2, Q8, Q13 and Q19 could control the migration of SMMC-7721 cells effectively, and inhibit the proliferation of cancer cells by inhibiting the DNA replication. Western-blot results showed that compounds Q2 and Q8 induced irreversible apoptosis of SMMC-7721 cells by regulating the expression level of apoptose-related proteins. Those studies demonstrated that the penta-1,4-diene-3-one derivatives containing quinazoline and oxime ether fragments merited further research as potential anticancer agents.
- Su, Shijun,Chen, Mei,Li, Qin,Wang, Yihui,Chen, Shuai,Sun, Nan,Xie, Chengwei,Huai, Ziyou,Huang, Yinjiu,Xue, Wei
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- 8-Hydroxyquinolin-2(1H)-one analogues as potential β2-agonists: Design, synthesis and activity study
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β2-Agonists that bind to plasmalemmal β2-adrenoceptors causing cAMP accumulation are widely used as bronchodilators in chronic respiratory diseases. Here, we designed and synthesized a group of 8-hydroxyquinolin-2(1H)-one analogues and studied their β2-agonistic activities with a cellular cAMP assay. Compounds B05 and C08 were identified as potent (EC50 2-agonists among the compounds tested. They behaved as partial β2-agonists in non-overexpressed HEK293 cells, and possessed rapid smooth muscle relaxant actions and long duration of action in isolated guinea pig tracheal strip preparations. In summary, B05 and C08 are β2-agonists with potential applicability in chronic respiratory diseases.
- Xing, Gang,Zhi, Zhengxing,Yi, Ce,Zou, Jitian,Jing, Xuefeng,Yiu-Ho Woo, Anthony,Lin, Bin,Pan, Li,Zhang, Yuyang,Cheng, Maosheng
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- Discovery and Characterization of Pure RhlR Antagonists against Pseudomonas aeruginosa Infections
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Pseudomonas aeruginosa (P. aeruginosa) is an opportunistic human pathogen that forms biofilms and produces virulence factors via quorum sensing (QS). Blocking the QS system in P. aeruginosa is an excellent strategy to reduce biofilm formation and the production of virulence factors. RhlR plays an essential role in the QS system of P. aeruginosa. We synthesized 55 analogues based on the chemical structure of 4-gingerol and evaluated their RhlR inhibitory activities using the cell-based reporter strain assay. Comprehensive structure-activity relationship studies identified the alkynyl ketone 30 as the most potent RhlR antagonist. This compound displayed selective RhlR antagonism over LasR and PqsR, strong inhibition of biofilm formation, and reduced production of virulence factors in P. aeruginosa. Furthermore, the survival rate of Tenebrio molitor larvae treated with 30 in vivo greatly improved. Therefore, compound 30, a pure RhlR antagonist, can be utilized for developing QS-modulating molecules in the control of P. aeruginosa infections.
- Nam, SangJin,Ham, So-Young,Kwon, Hongmok,Kim, Han-Shin,Moon, Suhyun,Lee, Jeong-Hoon,Lim, Taehyeong,Son, Sang-Hyun,Park, Hee-Deung,Byun, Youngjoo
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supporting information
p. 8388 - 8407
(2020/09/21)
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- Resolving Binding Events on the Multifunctional Human Serum Albumin
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Physiological processes rely on initial recognition events between cellular components and other molecules or modalities. Biomolecules can have multiple sites or mode of interaction with other molecular entities, so that a resolution of the individual binding events in terms of spatial localization as well as association and dissociation kinetics is required for a meaningful description. Here we describe a trichromatic fluorescent binding- and displacement assay for simultaneous monitoring of three individual binding sites in the important transporter and binding protein human serum albumin. Independent investigations of binding events by X-ray crystallography and time-resolved dynamics measurements (switchSENSE technology) confirm the validity of the assay, the localization of binding sites and furthermore reveal conformational changes associated with ligand binding. The described assay system allows for the detailed characterization of albumin-binding drugs and is therefore well-suited for prediction of drug-drug and drug-food interactions. Moreover, conformational changes, usually associated with binding events, can also be analyzed.
- Wenskowsky, Lea,Wagner, Michael,Reusch, Johannes,Schreuder, Herman,Matter, Hans,Opatz, Till,Petry, Stefan Matthias
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supporting information
p. 738 - 743
(2020/03/25)
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- Coumaric acid analogues inhibit growth and melanin biosynthesis in Cryptococcus neoformans and potentialize amphotericin B antifungal activity
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Fungal infections are on the rise, since the imunocompromised population is increasing due to AIDS/HIV, organ transplant and chemotherapy. Many environmental and pathogenic fungi are able to accomplish melanin biosynthesis as a virulence factor to promote host invasion. Melanized cells are more resistant to radiation, oxidative and osmotic stresses; also melanin confers an advantage in vivo, since melanized cells are more resistant to phagocytic engulfment and oxidative stress caused by the host defense cells and by some antifungal drugs, such as fluconazole (FCZ) and amphotericin B (AmB). Brown, red or black melanin pigments can be produced by the polyketide pathway (DHN-melanin) or from dihydroxyphenols, such as L-DOPA (L-3,4-dihydroxyphenylalanine) and L-tyrosine by polyphenoloxidases. Among several pathogenic fungi, Cryptococcus neoformans is a melanized yeast that causes pneumonia and meningoencephalitis in immunocompromised patients. The knockout of the laccase genes or other interruptions on melanin biosynthetic pathway generates cryptococcal strains with attenuated virulence in an animal model. In this study 16 analogues of coumaric and cinnamic acid were evaluated as possible tyrosinase inhibitors. We have identified some valuable inhibitors of C. neoformans growth and melanin biosynthesis disruption agents. The results showed that coumaric acid derivatives (1a-c), the ketones (3a-b) and 2-allylphenol (7c) are significant inhibitors of tyrosinase and melanization of the fungus. Two analogues (1b and 3b) were selected as promising antimelanogenic agents to be combined with AmB, showing to promote 16-fold reduction in the AmB fungicidal concentration with no appreciable cytotoxicity to mammalian cells. The data suggest that inhibition of the melanin biosynthesis by these compounds may increase the susceptibility of the cells to the oxidative stress generated by AmB. In summary, our data show that C. neoformans can be a suitable model system to test novel inhibitors that target melanin biosynthesis, and novel compounds for adjunct therapy against C. neoformans were identified.
- Melhem, Marcia S. C.,Oliveira, Lidiane,Pascon, Renata C.,Vallim, Marcelo A.,Varela, Marina Themoteo,dos Santos, Alexandre Paes,Corrêa, Isabela Teresa Santos,Fernandes, Jo?o Paulo S.,Ferrarini, Márcio,Tempone, André Gustavo
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- Selective oxidative hydroxylation of arylboronic acids by colloidal nanogold catalyzed in situ generation of H2O2 from alcohols under aerobic conditions
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Selective hydroxylation of arylboronic acids was achieved through PVP (polyvinylpyrrolidone)-stabilized nanogold catalyzed in situ generated H2O2 formed by the oxidation of an alcoholic solvent under aerobic conditions. The synthetic application of in situ generated H2O2 was investigated through aerobic epoxidation of (E)-chalcone.
- Sakurai, Hidehiro,Vinsen, Yuta Uetake
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p. 299 - 301
(2020/04/27)
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- Coumaric acid derivatives as tyrosinase inhibitors: Efficacy studies through in silico, in vitro and ex vivo approaches
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p-Coumaric acid is a known inhibitor of tyrosinase, an enzyme involved in the initial steps of the melanin synthesis in human and other species. However, its low lipophilicity impairs its penetration through skin and efficacy as antimelanogenic agent indeed. Accordingly, this paper reports the assessment of several coumaric acid derivatives as tyrosinase inhibitors and antimelanogenic agents in in vitro, in silico and ex vivo assays. The compounds were designed with modifications in the aromatic and acid moieties of p-coumaric acid, being the coumarate esters the most promising derivatives. The compounds showed higher tyrosinase inhibitory activity (pIC50 3.7–4.2) than the parent acid, being compounds 1d, 1e and 1f the most potent inhibitors. Docking analysis showed that these esters are competitive inhibitors per se, and act independently of a redox mechanism as suggested by DPPH assays. Moreover, the esters showed efficacy in reducing the melanin deposition in human skin fragments at 0.1% concentration, especially compound 1e. In summary, there is an important equilibria between tyrosinase affinity and lipophilicity that must be considered to get effective antimelanogenic agents with adequate permeability in the skin.
- Fernandes, Jo?o Paulo S.,Ferrarini, Márcio,Mercaldi, Vitória Gallo,Nazato, Lucas Idacir Sbrugnera,Padovani, Giovana,Sufi, Bianca da Silva,Varela, Marina Themoteo
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- Synthesis and biological evaluation of myricetin-pentadienone hybrids as potential anti-inflammatory agents in vitro and in vivo
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Some important pro-inflammatory cytokines such as interleukin-6, tumor necrosis factor-α and nitric oxide are thought to play key roles in the destruction of cartilage and bone tissue in joints affected by rheumatoid arthritis. In the present study, a series of new myricetin-pentadienone hybrids were designed and synthesized. Majority of them effectively inhibited the expressions liposaccharide-induced secretion of IL-6, TNF-α and NO in RAW264.7. The most prominent compound 5o could significantly decrease production of above inflammatory factors with IC50 values of 5.22 μM, 8.22 μM and 9.31 μM, respectively. Preliminary mechanism studies indicated that it could inhibit the expression of thioredoxin reductase, resulting in inhibiting of cell signaling pathway nuclear factor (N-κB) and mitogen-activated protein kinases. Significantly, compound 5o was found to effectively inhibit Freund's complete adjuvant induced rat adjuvant arthritis in vivo.
- Chen, Liu Zeng,Han, Xu,Liu, Chao,Liu, Xin Hua,Xue, Wei,Yu, Pei Jing
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supporting information
(2020/02/04)
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- PROCESS FOR THE PREPARATION OF RACTOPAMINE HYDROCHLORIDE VIA NOVEL INTERMEDIATES
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The present disclosure describes the new methods of preparation of Ractopamine which are superior to state of art by involving comparatively better and mild reaction conditions. The method of preparation involves following steps: In the first embodiment, 4-(4-hydroxyphenyl)-3-butene-2-one is prepared by condensation of 4-hydroxybenzaldehyde with acetone in the presence of sodium hydroxide/hydrochloric acid. In the next step, 4-(4-hydroxyphenyl)-3-butene-2-one undergoes hydrozination with 4-(-2-amino-1- hydroxyl ethyl) phenolhydrochloride in the presence of base using Pd/C/H2 as a catalyst in methanol/ethanol as solvent to yield Ractopamine base. In another embodiment, advancement over the previous scheme is use of Raney Ni/H2 instead of Pd/C as a catalyst. In yet another embodiment, 2-amino-1-(4-hydroxyphenyl) ethanone hydrochloride reacts with 4-(4-hydroxyphenyl)-butane -2-one in the presence of base and raney nickel/H2 as a catalyst. Compared to the prior art reports where Pd/C was used as a catalyst, Raney Ni is used in the present embodiment which is comparatively economical and better catalyst.
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Page/Page column 10
(2020/11/30)
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- 1,4-Pentadiene-3-ketone derivative with thiophene sulphonate and preparation method and application of derivative
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The invention discloses a 1,4-pentadiene-3-ketone derivative with thiophene sulphonate. The derivative is characterized in that the general formula of the derivative is shown in the following formula,wherein R is substituted phenyl or a substituted aromatic heterocyclic group. According to the derivative, 1-(4-hydroxy phenyl)-5-(substituted aryl)-1,4-pentadiene-3-ketone and thiophene sulphonate with good biological activity react to generate the 1,4-pentadiene-3-ketone derivative with the thiophene sulphonate, and when the concentration is 100 mcg/mL and 50 mcg/mL, the plant bacterium inhibition activity of a target compound is measured. It is proved through a bacterium inhibition activity testing result that at the experiment testing concentration, most compounds have good inhibition activity on xanthomonas oryzae, ralstonia solanacearum and xanthomonas citri and can be applied to preparation of an agent for inhibiting plant bacteria.
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Paragraph 0024; 0026; 0027
(2019/07/10)
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- Evaluation of the antitrypanosoma activity and SAR study of novel LINS03 derivatives
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Chagas’ disease is a parasitic infection caused by Trypanosoma cruzi that is still treated by old and toxic drugs. In the search for novel alternatives, natural sources are an important source for new drug prototypes against T. cruzi to further structural
- Varela, Marina T.,Costa-Silva, Thais A.,Lago, Jo?o Henrique G.,Tempone, Andre G.,Fernandes, Jo?o Paulo S.
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- Synthesis, antiviral and antibacterial activities and action mechanism of penta-1,4-dien-3-one oxime ether derivatives containing a quinoxaline moiety
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A series of penta-1,4-dien-3-one oxime ether derivatives containing a quinoxaline moiety were synthesized and their antibacterial and antiviral activities were evaluated. Bioassay activity indicated that some of the compounds displayed significant antibacterial and antiviral activities. In particular, some title compounds were found to show remarkable antiviral activities against tobacco mosaic virus (TMV). Compound 6i showed remarkable curative, protective and inactivation activity against TMV, with a 50% effective concentration (EC50) of 287.1, 157.6 and 133.0 μg mL-1, respectively. These results were better than or comparable to those of ningnanmycin (356.3, 233.7 and 121.6 μg mL-1, respectively). Microscale thermophoresis (MST) also showed that the binding of compound 6i to TMV coat protein (TMV-CP) gave a Kd value of 0.115 ± 0.092 μmol L-1, which was better than that of ningnanmycin (0.523 ± 0.254 μmol L-1). Meanwhile, the EC50 values of compound 6k against Xanthomonas axonopodis pv. Citri (Xac) and Xanthomonas oryzae pv. oryzae (Xoo) were 16.8 and 33.4 μg mL-1 respectively, and that of compound 6i against Ralstonia solanacearum (Rs) was 33.9 μg mL-1. These results were better than those of bismerthiazol (44.3, 42.5 and 62.4 μg mL-1, respectively). The mechanism of antibacterial action of compound 6k against Xac was analysed through scanning electron microscopy (SEM). This study indicated that the title compounds are valuable in the search for novel agrochemicals.
- Xia, Rongjiao,Guo, Tao,Chen, Mei,Su, Shijun,He, Jun,Tang, Xu,Jiang, Shichun,Xue, Wei
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p. 16461 - 16467
(2019/11/11)
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- Use of a switchable-hydrophilicity solvent as both a solvent and a catalyst in aldol condensation
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A switchable-hydrophilicity solvent, N,N-dimethylcyclohexylamine, was used as a recyclable catalyst and solvent for aldol condensation, giving >97% pure product in 94% isolated yield without the need for purification or additional solvents. CO2-triggered separation produced yields greater than conventional workup and allowed facile recycling of the amine.
- Poole, Hailey,Gauthier, Jeremy,Vanderveen, Jesse R.,Jessop, Philip G.,Lee, Roland
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supporting information
p. 6263 - 6267
(2019/12/03)
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- Benzothiazole-containing 1,4-pentadiene-3-one derivative as well as preparation method and application thereof
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The invention discloses a benzothiazole-containing 1,4-pentadienyl-3-one derivative, as well as a preparation method and application thereof. A general formula (I) is shown as the specification, wherein R is a phenyl group, a substituted phenyl or an aromatic heterocyclic group, the R-substituted phenyl group is one or more methyl or methoxy, trifluoromethyl, trifluoromethoxy, nitro, or one or more halogen atom-substituted phenyl group, and the R-substituted aromatic heterocyclic group is a thienyl group, a substituted naphthyl group or other heterocyclic groups. The benzothiazole-containing 1,4-pentadienyl-3-one derivative has relatively good resistance to tobacco mosaic virus, the reaction conditions are relatively mild, the post-treatment is simple, and the yield is relatively high.
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Paragraph 0126
(2019/01/23)
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- A thioether of triazole containing 1, 4 - pentadiene -3 - ketone derivatives, preparation method and use thereof
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The invention discloses a thioether of triazole containing 1, 4 - pentadiene - 3 - ketone derivatives, preparation method and use, its general structure is as follows, wherein: X is 2 - O or 4 - O, R is phenyl, substituted phenyl, heterocyclic base or 4 - methyl thiazole. The invention of tobacco mosaic virus, tobacco wilt bacteria in the dried bean curd is dry and rice pathogens and better control effect.
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Paragraph 0030; 0036
(2019/05/16)
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- Pentadienone compound containing triazine, and preparation method and application of pentadienone compound
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The invention relates to a pentadienone compound containing triazine, and a preparation method and an application of the pentadienone compound. The compound is shown as formula A as shown in the specification. X selected from O; R is phenyl, substituted phenyl or substituted heterocyclyl; R1 is a hydrogen atom or methoxyl; and R2 is phenyl, substituted phenyl or C1-C6 alkyl. The compound has a better prevention and control effect on pseudomonas solanacearum, xanthomonas citri and xanthomonas campestris pv. oryzae.
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Paragraph 0075; 0081-0082
(2019/09/17)
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- A benzene and three qinqin alkone of 1, 4 - pentadiene -3 - ketone derivatives, preparation method and use thereof
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The invention discloses a 1,4-pentadiene-3-ketone derivative containing benzotriazinone. The 1,4-pentadiene-3-ketone derivative containing benzotriazinone is characterized by having the general formula as shown in the specification, wherein R1 is phenyl, substituted phenyl (p-fluorophenyl, p-chlorophenyl, o-chlorophenyl, 2-methyoxyphenyl, 4-methyoxyphenyl, 4-methylphenyl, 2,4-dimethyoxyphenyl, 3,4-dimethyoxyphenyl, cinnamaldehyde group, 3-nitrophenyl, 2-chloro-5-nitrophenyl and the like), heterocyclic group (furyl, thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, pyrryl and the like) or substituted aromatic heterocyclic group (5-methyl thiazole, 5-methyl-2-thienyl, 4-bromo-2-thienyl and the like), and R2 is a hydrogen atom, methyl (ethyl), methoxyl (ethyoxyl) and the like. The compound disclosedby the invention has relatively high inhibiting activity for citrus canker bacteria, ralstonia solanacearum and tobacco mosaic viruses so as to be used for preparing an agricultural bactericide and anantiviral agent.
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Paragraph 0038; 0040
(2019/11/12)
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- Synthesis and antioxidant activity of caffeic acid derivatives
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A series of caffeic acid derivatives were synthesized via a modified Wittig reaction which is a very important tool in organic chemistry for the construction of unsaturated carbon–carbon bonds. All reactions were performed in water medium at 90?C. The aqueous Wittig reaction worked best when one unprotected hydroxyl group was present in the phenyl ring. The olefinations in the aqueous conditions were also conducted with good yields in the presence of two unprotected hydroxyl groups. When the number of the hydroxyl groups was increased to three, the reaction yields were worse, and the derivatives 12, 13, and 18 were obtained with 74%, 37%, and 70% yields, respectively. Nevertheless, the Wittig reaction using water as the essential medium is an elegant one-pot synthesis and a greener method, which can be a safe alternative for implementation in organic chemistry. The obtained compounds were tested for their antioxidant activity, and 12, 13, and 18 showed the highest activities. Moreover, all synthesized compounds displayed no cytotoxicity, and can therefore be used in the pharmaceutical or cosmetic industry.
- Sidoryk, Katarzyna,Jaromin, Anna,Filipczak, Nina,Cmoch, Piotr,Cybulski, Marcin
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- Two efficient pathways for the synthesis of aryl ketones catalyzed by phosphorus-free palladium catalysts
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Allylic alcohols, 1-buten-3-ol, 1-penten-3-ol and 1-octen-3-ol, reacted with aryl iodides (iodotoluene, 4-iodotoluene, 4-iodophenol and 4-iodanisole) under Heck reaction conditions to form corresponding saturated aryl ketones in one step. The same products were obtained in a two-step tandem reaction consisted of the Heck coupling of allylic alcohols with aryl iodides, followed by hydrogenation. Reactions were catalyzed by phosphorus-free palladium precursors modified with the menthol-substituted imidazolium chlorides. Formation of crystalline palladium nanoparticles, of the diameter up to 65 nm, in the reaction mixture was evidenced by TEM.
- Wirwis,Feder-Kubis,Trzeciak
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- Containing trimethylacetoxyl glucoside - 1, 4 - pentadiene - 3 - ketone compound and its preparation and use
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The invention discloses a preparation method of compounds for preventing and controlling plant virus disease: glucoside-1,4-pentadiene-3-ketone compounds containing acetoxyl groups and bioactivity, namely the compounds shown in the general formula (b) and a preparation method thereof. According to the preparation method, the glucoside-1, 4-pentadiene-3-ketone compounds containing the acetoxyl groups are synthesized by taking acetone, 2 or 4-substituted hydroxybenzaldehyde, substituted arylamine and acetyl bromoglucose as raw materials, ethanol and dichloromethane as solvents, dichloromethane as a catalyst and tetrabutylammonium bromide as a phase transfer catalyst. The compounds (f6), (f8), (f10), (f26) and (f28) have relatively good inhibitory effects on tobacco mosaic virus, cucumber mosaic virus and the like. The formula is shown in the description.
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Paragraph 0087-0088
(2018/03/26)
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- Diastereoselective synthesis of β-amino ketone and acid derivatives by palladium-catalyzed conjugate addition
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The first diastereoselective synthesis of β-amino ketone and β-amino acid derivatives by palladium-catalyzed conjugate addition of arylboronic acids to chiral β-enamino ketones and β-enamino esters is reported. The catalytic system employing (S)-4-(tert-butyl)oxazolidin-2-one as the chiral auxiliary in water under an air atmosphere provides β-amino ketone and β-amino acid derivatives in high yields with excellent diastereoselectivity.
- Zhi, Wubin,Li, Jingya,Zou, Dapeng,Wu, Yangjie,Wu, Yusheng
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supporting information
p. 2736 - 2740
(2018/06/25)
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- Quinoxaline-containing 1,4-pentadiene-3-one derivatives, and preparation method and application thereof
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The invention discloses quinoxaline-containing 1,4-pentadiene-3-one derivatives. The quinoxaline-containing 1,4-pentadiene-3-one derivatives are characterized by having a general formula which is as shown in the specification, wherein R1 is a phenyl, a substituted phenyl or a substituted aromatic heterocycle, and R2 one or more hydrogen atoms, methoxyls, nitryls, methyls, trifluoromethyls or halogen atoms contained on the 5-position, 6-position, 7-position and the 8-position of a quinoxaline structure. The compound provided by the invention has very good treating, protecting and passivating effects on TMV (Tobacco Mosaic Virus), shows high resistance to plant virus, and can be used for preparing a plant virus resisting pesticide.
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Paragraph 0041
(2018/03/28)
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- Quinazoline-containing 1,4-pentadiene-3-ketone oxime ether derivative as well as preparation method and application thereof
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The invention discloses a quinazoline-containing 1,4-pentadiene-3-ketone oxime ether derivative. The quinazoline-containing 1,4-pentadiene-3-ketone oxime ether derivative is characterized in that thegeneral formula is shown in the description, wherein R1 is phenyl, substituted phenyl or substituted heteroaromatic ring radical; R2 is phenyl, substituted phenyl or substituted heteroaromatic ring radical; R3 is one or more of hydrogen atoms, methoxyl groups, nitryl groups, methyl groups, trifluoromethyl groups or halogen atoms at 5-, 6-, 7- or 8-position of quinazoline. The compound provided bythe invention has good treatment and protection effects on cucumber mosaic virus (CMV) and tobacco mosaic virus (TMV), has higher plant virus activity resistance, and can be applied to preparation ofpesticides for resisting plant viruses.
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Paragraph 0048-0049
(2018/04/01)
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- A quinazoline of containing 1, 4 - pentadiene -3 - oxime ether derivatives, preparation method and application thereof (by machine translation)
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The invention discloses a containing the quinazoline of 1, 4 - pentadiene - 3 - oxime ether derivatives, preparation method and application thereof, the general formula (I) are as follows: Wherein R1 , R2 Is phenyl, substituted phenyl or substituted aryl heterocyclic group; R3 In the quinazoline of 5, 6, 7 or 8 position containing more than one hydrogen atom, methoxy, nitro, methyl, trifluoromethyl or halogen atom. The compounds of the invention to liver cancer SMMC - 7721 cell has excellent inhibitory activity, and exhibits a high anti-tumor activity, can be used as potential anti-tumor pharmaceutical use. (by machine translation)
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Paragraph 0016
(2018/10/11)
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- 1,4-pentadiene-3-one derivative containing phosphite ester as well as preparation method and application thereof
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The invention discloses a 1,4-pentadiene-3-one derivative containing phosphite ester as well as a preparation method and application thereof. According to the 1,4-pentadiene-3-one derivative containing phosphite ester, the general formula (I) of the 1,4-pentadiene-3-one derivative containing phosphite ester is as shown in the formula (I) in the specification, wherein R1 is a phenyl group, a substituted phenyl group or a substituted aromatic heterocyclic group, R2 is an alkyl group of C1-C6, the substituted phenyl group of the R1 is one or more methoxy group, nitro group, methyl group, trifluoromethyl group or halogen atom contained in ortho-, meta- and para- on a benzene ring or two positions of the ortho-, meta- and para- on the benzene ring, and the substituted aromatic heterocyclic group of R1 is a furan group, a pyridyl group, a thienyl group, a pyrrolyl group, a thiazolyl group, a 2-chloropyridine group or a 2-chlorothiazolyl group. The 1,4-pentadiene-3-one derivative as well as the preparation method and application thereof have the advantages that the activity of plant bacteria can be inhibited, the raw materials are easily available, the reaction conditions are mild, the post-treatment is simple, and the yield is high. The formula (I) is shown in the description.
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Paragraph 0030; 0032
(2018/12/14)
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- New pentadienone oxime ester derivatives: synthesis and anti-inflammatory activity
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To develop novel anti-inflammatory agents, a series of new pentadienone oxime ester compounds were designed and synthesized. The structures were determined by IR, 1H NMR, 13C NMR, and HRMS. All compounds have been screened for their anti-inflammatory activity by evaluating their inhibition against LPS-induced nitric oxide (NO) release in RAW 264.7 cell. Among them, compound 5j was found to be one of the most potent compounds in inhibiting NO and IL-6 (IC50 values were 6.66 μM and 5.07 μM, respectively). Preliminary mechanism studies show that title compound 5j could significantly suppress expressions of nitric oxide synthase, COX-2, and NO, IL-6 through Toll-like receptor 4/mitogen-activated protein kinases/NF-κB signalling pathway. These data support further studies to assess rational design of more efficient pentadienone oxime ester derivatives with anti-inflammatory activity in the future.
- Li, Qin,Zhang, Juping,Xue, Wei,Chen, Liu Zeng,Wang, Jie Quan,Tang, Wen Jian,Liu, Xin Hua,Zhou, Hai Ping
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p. 130 - 138
(2018/01/10)
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- Evaluation of sulphonamide derivatives acting as inhibitors of human carbonic anhydrase isoforms I, II and Mycobacterium tuberculosis β-class enzyme Rv3273
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A series of novel sulphonamide derivatives was obtained from sulphanilamide which was N4-alkylated with ethyl bromoacetate followed by reaction with hydrazine hydrate. The hydrazide obtained was further reacted with various aromatic aldehydes. The novel sulphonamides were characterised by infrared, mass spectrometry, 1H- and 13C-NMR and purity was determined by high-performance liquid chromatography (HPLC). Human (h) carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA I and II and Mycobacterium tuberculosis β-CA encoded by the gene Rv3273 (mtCA 3) inhibition activity was investigated with the synthesised compounds which showed promising inhibition. The KIs were in the range of 54.6 nM–1.8 μM against hCA I, in the range of 32.1 nM–5.5 μM against hCA II and of 127 nM–2.12 μM against mtCA 3.
- Wani, Tanvi V.,Bua, Silvia,Khude, Pravin S.,Chowdhary, Abdul H.,Supuran, Claudiu T.,Toraskar, Mrunmayee P.
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p. 962 - 971
(2018/05/29)
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- Novel curcumin analogue hybrids: Synthesis and anticancer activity
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In this study, twenty curcumin analogue hybrids as potential anticancer agents through regulation protein of TrxR were designed and synthesized. Results of anticancer activity showed that 5,7-dimethoxy-3-(3-(2-((1E, 4E)-3-oxo-5-(pyridin-2-yl)penta-1,4-dien-1- yl)phenoxy)propoxy)-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one (compound 7d) could induce gastric cancer cells apoptosis by arresting cell cycle, break mitochondria function and inhibit TrxR activity. Meanwhile, western blot revealed that this compound could dramatically up expression of Bax/Bcl-2 ratio and high expression of TrxR oxidation. These results preliminarily show that the important role of ROS mediated activation of ASK1/MAPK signaling pathways by this title compound.
- Wang, Jie Quan,Wang, Xiaobin,Wang, Yang,Tang, Wen Jian,Shi, Jing Bo,Liu, Xin Hua
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p. 493 - 509
(2018/07/25)
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- Synthesis of Enones and Enals via Dehydrogenation of Saturated Ketones and Aldehydes
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A general, efficient and economic palladium-catalyzed dehydrogenation to form enones or enals has been developed. The approach possesses extremely broad substrate scope including various linear or cyclic saturated ketones and aldehydes. The protocol is ligand-free, and molecular oxygen is used as the sole clean oxidant in the reaction. Due to mild reaction conditions, good functional group compatibility, and versatile utilities of enones and enals, the method can be applied in the late-stage synthesis of natural products, pharmaceuticals and fine chemicals. (Figure presented.).
- Pan, Gao-Fei,Zhu, Xue-Qing,Guo, Rui-Li,Gao, Ya-Ru,Wang, Yong-Qiang
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p. 4774 - 4783
(2018/11/10)
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- Poly(N-isopropylacrylamide-co-l-proline)-catalyzed Claisen-Schmidt and Knoevenagel condensations: Unexpected enhanced catalytic activity of the polymer catalyst
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The polymer catalyst is more effective than the corresponding monomer catalyst? Yes! The proline-modified polymer, poly(N-isopropylacrylamide-co-l-proline), was unexpectedly found to be more effective than the corresponding monomer l-proline catalyst in Claisen-Schmidt and Knoevenagel condensation reactions. 1H NMR, GC analysis and control reactions revealed that this abnormal phenomenon might be attributed to an enhanced concentration of the reactant on the surface of the polymer catalyst, which might be due to adsorption of the reactants to the polymer through hydrogen-bonding of the proline moiety with the reactants. This new polymer catalyst was so robust that it could be reused at least 10 times without deactivation. The polymer-catalyzed method was rather tolerant of substrates bearing sensitive groups that are usually incompatible with conventional acid- or base-catalyzed methods, reducing the protection-deprotection steps of the substrates.
- Zhang, Hao,Han, Mengting,Chen, Tian,Xu, Lin,Yu, Lei
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p. 48214 - 48221
(2017/11/03)
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- Retro-curcuminoids as mimics of dehydrozingerone and curcumin: Synthesis, NMR, X-ray, and cytotoxic activity
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Curcumin and its derivatives have been extensively studied for their remarkable medicinal properties, and their chemical synthesis has been an important step in the optimization of well-controlled laboratory production. A family of new compounds that mimic the structure of curcumin and curcuminoids, here named retro-curcuminoids (7-14), was synthesized and characterized using 1D 1H- and 13C-NMR, IR, and mass spectrometry; the X-ray structure of 7, 8, 9, 10, 12, 13, and 14 are reported here for the first time. The main structural feature of these compounds is the reverse linkage of the two aromatic moieties, where the acid chloride moiety is linked to the phenolic group while preserving α,β-unsaturated ketone functionality. The cytotoxic screening of 7, 8, 9, and 10 at 50 and 10 μg/mL was carried out with human cancer cell lines K562, MCF-7, and SKLU-1. Lipid peroxidation on rat brain was also tested for compounds 7 and 10. Compounds 7, 8, and 10 showed relevant cytotoxic activity against these cancer cell lines, and 10 showed a protective effect against lipid peroxidation. The molecular resemblance to curcuminoids and analogs with ortho substituents suggests a potential source of useful bioactive compounds.
- Obregón-Mendoza, Marco A.,Estévez-Carmona, María Mirian,Hernández-Ortega, Simón,Soriano-García, Manuel,Ramírez-Apan, María Teresa,Orea, Laura,Pilotzi, Hugo,Gnecco, Dino,Cassani, Julia,Enríquez, Raúl G.
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- Containing 1, 3, 4 - oxadiazole of thio pentadiene ketone compound of preparation method and use thereof
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The invention discloses a preparation method and biological activity of a pentadiene ketone compound, containing 1,3,4-oxadiazole sulfo-ethyoxyl, with a function of preventing and treating a plant virus disease, namely a compound expressed in a general formula (I) and a preparation method of the compound. According to the method, by using substituted carboxylic acid, hydrazine hydrate, carbon disulfide, acetone, 4-substituted hydroxy benzaldehyde, substituted aromatic aldehyde, 1,2-dibromoethane and the like as raw materials, methanol, ethanol and N,N-dimethylformamide as solvents and potassium carbonate, sodium hydroxide and potassium hydroxide as catalysts, pentadiene ketone compound containing 1,3,4-oxadiazole sulfo-ethyoxyl is prepared through seven-step synthesis. The compounds I3, I4, I6, I11, I13, I14, I16 and I17 have good functions in cucumber mosaic virus, tobacco mosaic virus, southern rice black-streaked dwarf virus and the like. The formula is shown in the specification.
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Paragraph 0115; 0116
(2017/07/31)
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- Cobalt-Catalyzed Carbonylative Cross-Coupling of Alkyl Tosylates and Dienes: Stereospecific Synthesis of Dienones at Low Pressure
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Despite advances in organometallic cross-coupling of alkyl electrophiles, there are few stereoselective reactions of chiral, nonracemic substrates. Herein we report a stereospecific carbonylative coupling of alkyl tosylates and dienes producing enantioenriched dienones. This catalytic process proceeds under low pressure and mild conditions using a simple cobalt catalyst and extends to diverse tosylate and diene coupling partners. The transformation constitutes a unique, convergent approach to the asymmetric synthesis of valuable carbonyl compounds from easily accessed starting materials.
- Sargent, Brendon T.,Alexanian, Erik J.
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supporting information
p. 12438 - 12440
(2017/09/25)
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- 1,4-pentadiene-3-ketone derivative containing coumarin, and preparation method and application thereof
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The invention discloses a 1,4-pentadiene-3-ketone derivative containing coumarin. The 1,4-pentadiene-3-ketone derivative containing the coumarin is characterized in that a general formula is shown as follows: (shown in the description), wherein R1 is phenyl, substituted phenyl or substituted aromatic heterocyclic group; R2 is one or more of hydrogen atoms, methoxyl, nitryl, methyl, trifluoromethyl or halogen atoms contained on site 5, 6, 7 or 8 of the coumarin structure. The compound has excellent inhibition activity for stomach cancer SGC7901 cells and liver cancer hepG2 cells, has relatively high antitumor activity and can be used as a potential antitumor drug.
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Paragraph 0037-0038; 0040
(2017/08/30)
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- 4(3H)-quinazolinone-containing 1,4-pentadiene-3-ketoxime ether derivatives and preparation method thereof
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The invention discloses 4(3H)-quinazolinone-containing 1,4-pentadiene-3-ketoxime ether derivatives. The 4(3H)-quinazolinone-containing 1,4-pentadiene-3-ketoxime ether derivatives are characterized in that the general formula of the derivatives is described in the description, wherein R1 is phenyl, substituted phenyl or substituted aromatic heterocyclic group; R2 is phenyl, substituted phenyl or substituted aromatic heterocyclic group; R3 is one or more hydrogen atoms, methoxy group, nitro group, methyl group, trifluoromethyl group or halogen atoms contained in the 5, 6, 7 or 8 site of 4(3H)-quinazolinone. The compounds provided by the invention have higher treatment and protection functions for cucumber mosaic virus (CMV) and tobacco mosaic virus (TMV), and shows better plant virus resisting activity, thus being used for preparing anti-plant-virus pesticides.
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Paragraph 0059; 0060; 0075; 0076; 0091; 0092; 0107; 0108
(2017/08/29)
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- Structure-Activity Relationships of 6- and 8-Gingerol Analogs as Anti-Biofilm Agents
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Pseudomonas aeruginosa is a causative agent of chronic infections in immunocompromised patients. Disruption of quorum sensing circuits is an attractive strategy for treating diseases associated with P. aeruginosa infection. In this study, we designed and synthesized a series of gingerol analogs targeting LasR, a master regulator of quorum sensing networks in P. aeruginosa. Structure-activity relationship studies showed that a hydrogen-bonding interaction in the head section, stereochemistry and rotational rigidity in the middle section, and optimal alkyl chain length in the tail section are important factors for the enhancement of LasR-binding affinity and for the inhibition of biofilm formation. The most potent compound 41, an analog of (R)-8-gingerol with restricted rotation, showed stronger LasR-binding affinity and inhibition of biofilm formation than the known LasR antagonist (S)-6-gingerol. This new LasR antagonist can be used as an early lead compound for the development of anti-biofilm agents to treat P. aeruginosa infections.
- Choi, Hyunsuk,Ham, So-Young,Cha, Eunji,Shin, Yujin,Kim, Han-Shin,Bang, Jeong Kyu,Son, Sang-Hyun,Park, Hee-Deung,Byun, Youngjoo
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p. 9821 - 9837
(2017/12/26)
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- Biocatalytic Properties and Structural Analysis of Eugenol Oxidase from Rhodococcus jostii RHA1: A Versatile Oxidative Biocatalyst
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Eugenol oxidase (EUGO) from Rhodococcus jostii RHA1 had previously been shown to convert only a limited set of phenolic compounds. In this study, we have explored the biocatalytic potential of this flavoprotein oxidase, resulting in a broadened substrate scope and a deeper insight into its structural properties. In addition to the oxidation of vanillyl alcohol and the hydroxylation of eugenol, EUGO can efficiently catalyze the dehydrogenation of various phenolic ketones and the selective oxidation of a racemic secondary alcohol—4-(1-hydroxyethyl)-2-methoxyphenol. EUGO was also found to perform the kinetic resolution of a racemic secondary alcohol. Crystal structures of the enzyme in complexes with isoeugenol, coniferyl alcohol, vanillin, and benzoate have been determined. The catalytic center is a remarkable solvent-inaccessible cavity on the si side of the flavin cofactor. Structural comparison with vanillyl alcohol oxidase from Penicillium simplicissimum highlights a few localized changes that correlate with the selectivity of EUGO for phenolic substrates bearing relatively small p-substituents while tolerating o-methoxy substituents.
- Nguyen, Quoc-Thai,de Gonzalo, Gonzalo,Binda, Claudia,Rioz-Martínez, Ana,Mattevi, Andrea,Fraaije, Marco W.
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p. 1359 - 1366
(2016/08/31)
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- Identification of a new curcumin synthase from ginger and construction of a curcuminoid-producing unnatural fusion protein diketide-CoA synthase::curcumin synthase
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The biosynthesis and metabolic engineering of curcuminoids received considerable attention for their important pharmaceutical properties. In the present study, a new curcumin synthase (ZoCURS) was identified from ginger (Zingiber officinale). Notably, ZoCURS efficiently accepts 3-(4-hydroxyphenyl)propionyl-CoA to produce tetrahydrobisdemethoxycurcumin, which would be meaningful to further understand the biosynthesis of curcuminoids in ginger. In addition, a curcuminoid-producing unnatural fusion protein diketide-CoA synthase::curcumin synthase (DCS::CURS) was constructed. Comparing to ZoCURS, DCS::CURS indicated similar substrate specificities and catalytic potentials to catalyze the formation of various curcuminoids, however, the yield of curcuminoids produced by DCS::CURS was obviously increased, which would be useful for metabolic engineering of pharmaceutically important curcuminoid analogs, particularly including asymmetric dihydrocurcuminoids such as 3-(4-hydroxyphenyl)propionyl-feruloylmethane, 3-(4-hydroxyphenyl)propionyl-p-coumaroylmethane, and 3-(4-hydroxyphenyl)propionyl-cinnamoylmethane.
- Zhang, Le,Gao, Bowen,Wang, Xiaohui,Zhang, Zhongxiu,Liu, Xiao,Wang, Juan,Mo, Ting,Liu, Yuyu,Shi, Shepo,Tu, Pengfei
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p. 12519 - 12524
(2016/02/12)
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- Containing purine pentadiene ketone derivative synthesis method and application
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The invention discloses a compound with an effect for resisting plant viruses, and relates to a preparation method and an application of a purine-containing pentadienone derivatives with an effect of resisting the plant viruses. A series of purine-containing pentadienone derivatives are synthesized in five steps by adopting 6-chloropurine, thiourea, absolute ethyl alcohol, methanoic acid, p-hydroxy benzaldehyde, sodium hydroxide, potassium hydroxide, acetone, hydrochloric acid, substituted aromatic aldehyde and substituted heterocyclic aldehydes as raw materials. The invention also discloses compounds A1, A3, A5, A7, A11, A12 and A17, which have a curative, protective and passivation effect on CMV, TMV and SRBSDV, and are relatively high in plant virus resistant activity and can be used for preparing new chemicals for preventing the plant virus diseases.
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Paragraph 0057; 0060; 0061
(2020/02/07)
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- Discovery of New Monocarbonyl Ligustrazine-Curcumin Hybrids for Intervention of Drug-Sensitive and Drug-Resistant Lung Cancer
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The elevation of oxidative stress preferentially in cancer cells by inhibiting thioredoxin reductase (TrxR) and/or enhancing reactive oxygen species (ROS) production has emerged as an effective strategy for selectively targeting cancer cells. In this study, we designed and synthesized 21 ligustrazine-curcumin hybrids (10a-u). Biological evaluation indicated that the most active compound 10d significantly inhibited the proliferation of drug-sensitive (A549, SPC-A-1, LTEP-G-2) and drug-resistant (A549/DDP) lung cancer cells but had little effect on nontumor lung epithelial-like cells (HBE). Furthermore, 10d suppressed the TrxR/Trx system and promoted intracellular ROS accumulation and cancer cell apoptosis. Additionally, 10d inhibited the NF-κB, AKT, and ERK signaling, P-gp-mediated efflux of rhodamine 123, P-gp ATPase activity, and P-gp expression in A549/DDP cells. Finally, 10d repressed the growth of implanted human drug-resistant lung cancer in mice. Together, 10d acts a novel TrxR inhibitor and may be a promising candidate for intervention of lung cancer.
- Ai, Yong,Zhu, Bin,Ren, Caiping,Kang, Fenghua,Li, Jinlong,Huang, Zhangjian,Lai, Yisheng,Peng, Sixun,Ding, Ke,Tian, Jide,Zhang, Yihua
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p. 1747 - 1760
(2016/03/25)
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- Traceless OH-Directed Wacker Oxidation-Elimination, an Alternative to Wittig Olefination/Aldol Condensation: One-Pot Synthesis of α,β-Unsaturated and Nonconjugated Ketones from Homoallyl Alcohols
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A new method for one-pot synthesis of β-substituted and β,β-disubstituted α,β-unsaturated methyl ketones from homoallyl alcohols by sequential PdCl2/CrO3-promoted Wacker process followed by an acid-mediated dehydration reaction has been developed. Remarkably, internal homoallyl alcohols delivered regioselectively nonconjugated unsaturated carbonyl compounds under the same protocol. A new starting material-based synthesis of α,β-unsaturated and nonconjugated methyl ketones is demonstrated.
- Bethi, Venkati,Fernandes, Rodney A.
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p. 8577 - 8584
(2016/09/28)
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- Organocatalyzed Asymmetric Conjugate Addition of Heteroaryl and Aryl Trifluoroborates: A Synthetic Strategy for Discoipyrrole D
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Bis-heteroaryl or bis-aryl stereocenters were formed by an organocatalytic enantioselective conjugate addition using the respective trifluoroborate salts as nucleophiles. Control studies suggested that fluoride dissociation is necessary in the anhydrous conditions. This strategy is applicable to the synthesis of discoipyrrole D, an inhibitor of BR5 fibroblast migration.
- Shih, Jiun-Le,Nguyen, Thien S.,May, Jeremy A.
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supporting information
p. 9931 - 9935
(2015/08/19)
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