cas 3160-35-8, 4-Hydroxybenzylideneacetone

Articles about 3160-35-8Total 45 be found

Article title
Article abstract
Author
Journal number and time
Download

Novel penta-1,4-diene-3-one derivatives containing quinazoline and oxime ether fragments: Design, synthesis and bioactivity
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
(2021/01/18)

8-Hydroxyquinolin-2(1H)-one analogues as potential β2-agonists: Design, synthesis and activity study
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
(2021/07/19)

Selective oxidative hydroxylation of arylboronic acids by colloidal nanogold catalyzed in situ generation of H2O2 from alcohols under aerobic conditions
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
p. 299 - 301
(2020/04/27)

Coumaric acid derivatives as tyrosinase inhibitors: Efficacy studies through in silico, in vitro and ex vivo approaches
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
(2020/08/06)

Synthesis and biological evaluation of myricetin-pentadienone hybrids as potential anti-inflammatory agents in vitro and in vivo
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
supporting information

(2020/02/04)

PROCESS FOR THE PREPARATION OF RACTOPAMINE HYDROCHLORIDE VIA NOVEL INTERMEDIATES
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.
-
Page/Page column 10

(2020/11/30)

Use of a switchable-hydrophilicity solvent as both a solvent and a catalyst in aldol condensation
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
supporting information
p. 6263 - 6267
(2019/12/03)

Benzothiazole-containing 1,4-pentadiene-3-one derivative as well as preparation method and application thereof
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.
-
Paragraph 0126

(2019/01/23)

A thioether of triazole containing 1, 4 - pentadiene -3 - ketone derivatives, preparation method and use thereof
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.
-
Paragraph 0030; 0036

(2019/05/16)

Pentadienone compound containing triazine, and preparation method and application of pentadienone compound
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.
-
Paragraph 0075; 0081-0082

(2019/09/17)

A benzene and three qinqin alkone of 1, 4 - pentadiene -3 - ketone derivatives, preparation method and use thereof
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.
-
Paragraph 0038; 0040

(2019/11/12)

Two efficient pathways for the synthesis of aryl ketones catalyzed by phosphorus-free palladium catalysts
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
p. 61 - 72
(2018/01/05)

Diastereoselective synthesis of β-amino ketone and acid derivatives by palladium-catalyzed conjugate addition
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
supporting information
p. 2736 - 2740
(2018/06/25)

Quinoxaline-containing 1,4-pentadiene-3-one derivatives, and preparation method and application thereof
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.
-
Paragraph 0041

(2018/03/28)

Quinazoline-containing 1,4-pentadiene-3-ketone oxime ether derivative as well as preparation method and application thereof
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.
-
Paragraph 0048-0049

(2018/04/01)

A quinazoline of containing 1, 4 - pentadiene -3 - oxime ether derivatives, preparation method and application thereof (by machine translation)
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)
-
Paragraph 0016

(2018/10/11)

1,4-pentadiene-3-one derivative containing phosphite ester as well as preparation method and application thereof
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.
-
Paragraph 0030; 0032

(2018/12/14)

New pentadienone oxime ester derivatives: synthesis and anti-inflammatory activity
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
p. 130 - 138
(2018/01/10)

Evaluation of sulphonamide derivatives acting as inhibitors of human carbonic anhydrase isoforms I, II and Mycobacterium tuberculosis β-class enzyme Rv3273
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.
p. 962 - 971
(2018/05/29)

Novel curcumin analogue hybrids: Synthesis and anticancer activity
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
p. 493 - 509
(2018/07/25)

Synthesis and antiviral activities of novel penta-1,4-diene-3-one oxime derivatives bearing a pyridine moiety
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
p. 1225 - 1233
(2017/06/19)

1,4-pentadiene-3-ketone derivative containing coumarin, and preparation method and application thereof
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.
-
Paragraph 0037-0038; 0040

(2017/08/30)

4(3H)-quinazolinone-containing 1,4-pentadiene-3-ketoxime ether derivatives and preparation method thereof
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.
-
Paragraph 0059; 0060; 0075; 0076; 0091; 0092; 0107; 0108

(2017/08/29)

Structure-Activity Relationships of 6- and 8-Gingerol Analogs as Anti-Biofilm Agents
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
p. 9821 - 9837
(2017/12/26)

Biocatalytic Properties and Structural Analysis of Eugenol Oxidase from Rhodococcus jostii RHA1: A Versatile Oxidative Biocatalyst
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.
p. 1359 - 1366
(2016/08/31)

Identification of a new curcumin synthase from ginger and construction of a curcuminoid-producing unnatural fusion protein diketide-CoA synthase::curcumin synthase
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
p. 12519 - 12524
(2016/02/12)

Containing purine pentadiene ketone derivative synthesis method and application
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.
-
Paragraph 0057; 0060; 0061

(2020/02/07)

Discovery of New Monocarbonyl Ligustrazine-Curcumin Hybrids for Intervention of Drug-Sensitive and Drug-Resistant Lung Cancer
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
p. 1747 - 1760
(2016/03/25)

Preparation of a raspberry ketone precursor in the presence of rare earth oxide catalysts
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
p. 654 - 663
(2015/10/05)

Catalytic microwave-promoted direct aldol condensation using resin-bound secondary amine
A series of polystyrene-supported imino group-bearing catalysts were prepared. A highly efficient combination of recyclable catalysts and microwave irradiation was developed as a green protocol for the direct aldol reaction. Notably, microwaves greatly shorten the reaction times to only 20 min and improve the yield significantly. Catalyst loading was reduced as well. Different aromatic aldehydes as aldol donors were subjected to our catalyst system and afforded the corresponding products in satisfactory yields. Additionally, the polymer-supported catalysts could be recovered by simple filtration and were reusable for at least four times without significant loss of reactivity. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]
Liao, Fu Xu,Wang, Yu Guang,Zhu, Qing
supporting information
p. 161 - 169
(2013/12/04)

Synthesis and biological evaluation of unsymmetrical curcumin analogues as tyrosinase inhibitors
Synthesis and biological evaluation of unsymmetrical curcumin analogues (UCAs) have been achieved. Tyrosinase inhibitory activities were found for most of the prepared synthetic UCAs. Among them, compounds containing 4-hydroxyl-substituted phenolic rings with C-2/C-4- or C-3/C-4-dihydroxyl- substituted diphenolic rings were more active (IC50 = 1.74~16.74 μM) than 4-butylresorcinol and kojic acid, which suggested that the 4-hydroxyl groups in UCAs play a crucial role in tyrosinase inhibitory activities. The inhibition kinetics analyzed by Lineweaver-Burk plots revealed compounds 3c and 3i containing catecholic rings were mixed-competitive inhibitors, whereas compounds 3d and 3j containing resorcinolic rings were competitive inhibitors. The preliminary evaluation results of acute toxicity showed the representative 3d and 3j were non-toxic in mice dosed at 1,200 mg/kg. This research suggests that, with the advantage of being readily prepared small molecules, polyphenolic UCAs have the potential to develop into pharmacological inhibitors of tyrosinase.
Jiang, Yongfu,Du, Zhiyun,Xue, Guihua,Chen, Qian,Lu, Yujing,Zheng, Xi,Conney, Allan H.,Zhang, Kun
p. 3948 - 3961
(2013/06/05)

FLAVONE DERIVATIVES AND THEIR PREPARATIVE METHOD AND MEDICAL USE
Flavone derivatives, preparative method of the derivatives and use thereof as medicaments for treating diabetes. The structure of the derivatives is presented by formula 1: In the structure, R1 and R2, which are identical or not, represent hydrogen atom, halogen, cyano, hydroxyl, trifluoromethyl, thio-methyl, benzyloxy, C1-C8 linear chain or branch chain alkyl, C1-C8 linear chain or branch chain alkoxy. The pharmacological test indicates that the flavone derivatives can significantly increase the glucose consumption of Hep-G2 cell with insulin resistance activity, promote translocation of glucose transporter 4 of skeletal muscle cells (L6GLUT4myc) at different level, and significantly increase glucose intake and utilization by cells. The test proves the fact for the first time that the flavone derivatives can significantly promote translocation of glucose transporter 4 of skeletal muscle cells, and one of the mechanisms for treating diabetes is activating the cell AMPK phosphorylation and phosphorylating the downstream ACC.
-
Paragraph 0028

(2013/09/12)

Carbene based palladium-catalyzed Mizoroki-Heck reaction
Different perhydrobenzimidazolinium chloride salts were used as a ligand for PdcatalysedMizoroki-Heck reaction. The in situ generation of carbene is the attractive feature of this catalytic system. The corresponding Mizoroki-Heck products were obtained in good yield.
Srivastava, Vivek
p. 1859 - 1863
(2013/06/27)

Effect of the Aggregation of 4-[5-(4-Hydroxyphenyl)-3-oxopenta- 1,4-dienyl]benzoic Acid and Its Potassium Salt in a Polymeric Matrix on the Third-Order Nonlinear Optical Susceptibility of Polymer-Chromophore Composites
Aggregation of 4-[5-(4-hydroxyphenyl)-3-oxopenta-1,4-dienyl]benzoic acid (chromophore) and its potassium salt in optically neutral polymeric matrices was studied. The dependence of the third-order nonlinear optical properties of the chromophore-polymer composites on the aggregate size was determined.
Savitsky, A. O.,Vinogradova, L. V.,Bursian, A. E.,Ten'kovtsev, A. V.,Lukoshkin, V. A.
p. 1422 - 1427,6
(2020/09/16)

A scalable two-step continuous flow synthesis of nabumetone and related 4-aryl-2-butanones
Three different continuous flow strategies for the generation of important 4-aryl-2-butanone derivatives including the anti-inflammatory drug nabumetone [4-(6-methoxy-2-naphthalenyl)-2-butanone] and the aroma compounds raspberry ketone [4-(4-hydroxyphenyl)-2-butanone] and its methyl ether [4-(4-methoxyphenyl)-2-butanone] were evaluated. All three protocols involve the initial preparation of the corresponding 4-aryl-3-buten-2-ones via Mizoroki-Heck, Wittig, or aldol strategies, which is then followed by selective hydrogenation of the C=C double bond to the desired 4-aryl-2-butanones. The synthetic routes to 4-aryl-3-buten-2-ones were first optimized/intensified on small scale to reaction times of 1-10 min using batch microwave heating technology and then translated to a scalable continuous flow process employing commercially available stainless steel capillary tube reactors. For the synthesis of 4-(4-methoxyphenyl)-3-buten-2-one a further scale-up using a custom-built mesofluidic mini-plant flow system capable of processing several liters per hour was designed to further expand the scale of the process. The final hydrogenation step was performed using a fixed-bed continuous flow hydrogenator employing Ra/Ni as a catalyst.
Viviano, Monica,Glasnov, Toma N.,Reichart, Benedik,Tekautz, Guenter,Kappe, C. Oliver
experimental part
p. 858 - 870
(2012/06/30)

Organocatalyst-mediated aldolrobinson cascade reactions: A convenient synthesis of substituted cyclohex-2-enones
A convenient organocatalytic process for the chemoselective synthesis of substituted cyclohex-2-enones was developed. The cascade reaction involves a remarkable Michael addition of an acyclic ketone-based enamine onto unmodified enones. The enamine-mediated aldolRobinson cascade reactions of aromatic and aliphatic aldehydes with acetone produced substituted cyclohex-2-enones in moderate to high yields under mild reaction conditions.
Wang, Li,Gong, Qing-Ping,Liu, Xiao-Jun,Li, Yong-Hong,Huang, Ping,Wang, Bi-Qin,Zhao, Ke-Qing
experimental part
p. 138 - 139
(2011/04/15)

Enone- and chalcone-chloroquinoline hybrid analogues: In silico guided design, synthesis, antiplasmodial activity, in vitro metabolism, and mechanistic studies
Analogues of the previously reported antimalarial hybrid compounds 8b and 12 were proposed with the aim of identifying compounds with improved solubility and retained antimalarial potency. In silico characterization predicted improved solubilities of the analogues, particularly at low pH; they retained acceptable predicted permeability properties but were predicted to be susceptible to hepatic metabolism. These analogues were synthesized and found to exhibit notable in vitro antimalarial activity. Compounds 25 and 27 were the most active of the analogues. In vitro metabolism studies indicated susceptibility of the analogues to hepatic metabolism. There was also evidence of primary glucuronidation for analogues 24-27. Presumed cis-trans isomerism of 12, 22, and 23 under in vitro metabolism assay conditions was also observed, with differences in the nature and rates of metabolism observed between isomers. Biochemical studies strongly suggested that inhibition of hemozoin formation is the primary mechanism of action of these analogues.
Guantai, Eric M.,Ncokazi, Kanyile,Egan, Timothy J.,Gut, Jiri,Rosenthal, Philip J.,Bhampidipati, Ravi,Kopinathan, Anitha,Smith, Peter J.,Chibale, Kelly
experimental part
p. 3637 - 3649
(2011/07/09)

Di(ortho-hydroxybenzylidene)acetone as a new acid-base indicator and a chromogenic receptor for anions and guanidine
The development of a new simple acid-base indicator di(o- hydroxybenzylidene)acetone (1) is reported as a possible alternative to phenolphthalein and its performance has been compared with those of o-hydroxybenzylideneacetone (2) and p-hydroxybenzylideneacetone (3), two synthetic compounds, and curcumin (4), a natural product occurring in turmeric. Among the four compounds, 1 is found to be the best. It may also be used in the titration of guanidine in non-aqueous solvents (e.g. in dry alcohol). It is also shown to be a chemosensor for anions.
Goswami, Shyamaprosad,Chakrabarty, Rinku
experimental part
p. 547 - 557
(2012/03/26)

Synthesis and biological activity of novel tiliroside derivants
A series of new tiliroside derivatives were synthesized and characterized by analytical 1H NMR, 13C NMR and mass spectrometry. All of the compounds were evaluated for anti-diabetic properties in vitro using HepG2 cells. Compounds 3c, 3d, and 3i-l caused significant enhancements in glucose consumption by insulin-resistant HepG2 cells compared with control cells and cells that were exposed to metformin (an anti-diabetic drug). Moreover, compound 3l significantly activated adenosine 5′-monophosphate-activated protein kinase activity and reduced acetyl-CoA carboxylase activity. Thus, the tiliroside derivative 3l offers potential to be developed as a new approach for treating type II diabetes.
Qin, Nan,Li, Chun-Bao,Jin, Mei-Na,Shi, Li-Huan,Duan, Hong-Quan,Niu, Wen-Yan
scheme or table
p. 5189 - 5195
(2011/11/14)

Protection-, salt-, and metal-free syntheses of [n]-shogaols by use of dimethylammonium dimethyl carbamate (DIMCARB) without protecting groups
Shogaols, the pungent principle of ginger, exhibit interesting bioactivities. Practical preparation of shogaols is highly desired. Here we report the protection/deprotection-, salt-, and metalfree synthesis of shogaol in three steps by use of dimethylammonium dimethyl carbamate (DIMCARB), in which DIMCARB smoothly promoted Mannich-type condensation of the ketone donor with the aldehyde acceptor through the iminium cation intermediate. Georg Thieme Verlag Stuttgart.
Mase, Nobuyuki,Kitagawa, Norihiko,Takabe, Kunihiko
experimental part
p. 93 - 96
(2010/07/16)

Synthesis and molecular docking studies of novel 2-chloro-pyridine derivatives containing flavone moieties as potential antitumor agents
A series of novel 2-chloro-pyridine derivatives containing flavone, chrome or dihydropyrazole moieties as potential telomerase inhibitors were synthesized. The bioassay tests showed that compounds 6e and 6f exhibited some effect against gastric cancer cell SGC-7901 with IC50 values of 22.28 ± 6.26 and 18.45 ± 2.79 μg/mL, respectively. All title compounds were assayed for telomerase inhibition by a modified TRAP assay, the results showed that compound 6e can strongly inhibit telomerase with IC50 value of 0.8 ± 0.07 μM. Docking simulation was performed to position compound 6e into the active site of telomerase (3DU6) to determine the probable binding model.
Liu, Xin-Hua,Liu, Hui-Feng,Shen, Xu,Song, Bao-An,Bhadury, Pinaki S.,Zhu, Hai-Liang,Liu, Jin-Xing,Qi, Xing-Bao
scheme or table
p. 4163 - 4167
(2010/08/20)

Benzoyl 2-methyl indoles as selective PPARγ modulators
A series of selective PPARγ modulators (SPPARγMs) and their development from hPPARγ active screening leads 1 and 2 is described. SPPARγM 24 displayed robust anti-diabetic activity with an improved therapeutic window in comparison to a PPARγ full agonist in a rodent efficacy model. Routine screening for human PPAR ligands yielded compounds 1 and 2, both of which were sub-micromolar hPPARγ agonists. Synthetic modifications of these leads led to a series of potent substituted 3-benzyl-2-methyl indoles, a subset of which were noted to be selective PPARγ modulators (SPPARγMs). SPPARγM 24 displayed robust anti-diabetic activity with an improved therapeutic window in comparison to a PPARγ full agonist in a rodent efficacy model.
Acton III, John J.,Black, Regina M.,Jones, A. Brian,Moller, David E.,Colwell, Lawrence,Doebber, Thomas W.,MacNaul, Karen L.,Berger, Joel,Wood, Harold B.
p. 357 - 362
(2007/10/03)

Correspondence between Molecular Functionality and Crystal Structures. Supramolecular Chemistry of a Family of Homologated Aminophenols
The crystal structures and packing features of a family of 13 aminophenols, or supraminols, are analyzed and correlated. These compounds are divided into three groups: (a) compounds 1-5 with methylene spacers of the general type HO-C6H4-(CH2)n- C6H 4-NH2 (n = 1 to 5) and both OH and NH2 in a para position; (b) compounds la, 2a, 2b, 2c, and 3a in which one or more of the methylene linkers in 1 to 3 are exchanged with an S-atom; and (c) compounds 2d, 1b, and 6a prepared with considerations of crystal engineering and where the crystal structures may be anticipated on the basis of structures 1-5, 1a, 2a, 2b, 2c, and 3a. These 13 aminols can be described in terms of three major supramolecular synthons based on hydrogen bonding between OH and NH2 groups: the tetrameric loop or square motif, the infinite N(H)O chain, and β-As sheet. These three synthons are not completely independent of each other but interrelate, with the structures tending toward the more stable β-As sheet in some cases. Compounds 1-5 show an alternation in melting points, and compounds with n = even exhibit systematically higher melting points compared to those with n = odd. The alternating melting points are reflected in, and explained by, the alternation in the crystal structures. The n = odd structures tend toward the β-As sheet as n increases and can be considered as a variable series whereas for n = even, the β-As sheet is invariably formed constituting a fixed series. Substitution of a methylene group by an isosteric S-atom may causes a change in the crystal structure. These observations are rationalized in terms of geometrical and chemical effects of the functional groups. This study shows that even for compounds with complex crystal structures the packing may be reasonably anticipated provided a sufficient number of examples are available.
Vangala, Venu R.,Bhogala, Balakrishna R.,Dey, Archan,Desiraju, Gautam R.,Broder, Charlotte K.,Smith, Philip S.,Mondal, Raju,Howard, Judith A. K.,Wilson, Chick C.
p. 14495 - 14509
(2007/10/03)

Microwave induced rate enhancement in aldol condensation
The rate of formation of aldol condensed products using microwave of various aromatic aldehydes and ketones in aqueous medium dramatically enhanced with respect to conventional methods in high yield (50-95.2%).
Kad,Kaur, Kanwal Preet,Singh, Vasundhara,Singh, Jasvinder
p. 2583 - 2586
(2007/10/03)

Reaction of Propargyl Bromide with Aldehydes in the Presence of Metallic Tin. Synthesis of Homopropargylalcohols and Homoallenylalcohols
In the presence of water, metallic tin and propargyl bromide reacted smoothly with aldehydes to give the corresponding homopropargyl alcohols (a) and homoallenyl alcohols (b).High chemospecifity to bifunctional carbonyl compounds containing -OH, -X and -NO2 etc. was obtained.
Wu, Shihui,Huang, Bangzhou,Gao, Xiang
p. 1279 - 1286
(2007/10/02)