- Design of chromogenic probes for efficient screening and evaluation of feruloyl esterase-like activities
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Feruloyl esterases (FAEs) constitute an important sub-group of hydrolytic enzymes involved in the deconstruction of plant cell wall polysaccharides. However, in the current era of genomics and metagenomics, finding and characterizing FAEs is not straightf
- Gherbovet, Olga,Fauré, Régis,Ferreira, Fernando,Durand, Julien,Ragon, Mélanie,Hostyn, Guillaume,Record, Eric,Bozonnet, Sophie,O'Donohue, Michael J.
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Read Online
- Development trans-N-benzyl hydroxyl cinnamamide based compounds from cinnamic acids and characteristics anticancer potency
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The derivatization of three hydroxycinnamamides becomes trans-N-benzylhydroxycinnamamides, and their potential assay as anticancer agents has been carried out. N-benzyl-p-coumaramide (5a), N-benzylcaffeamide (5b), and N-benzylferulamide (5c) were obtained
- Agustan, Agustan,Bahriah, Bahriah,Dali, Seniwati,Firdausiah, Syadza,Rasyid, Herlina,Soekamto, Nunuk Hariani,Tahir, Dahlang,Zenta, Firdaus
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- Stable isotopic labelling of β-sitosteryl ferulate for use as analytical tool
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Rice is one of the major staple foods consumed worldwide and due to the presence of γ-oryzanol (γ-OZ) it is well-recognized as functional food. For this reason, the most appropriate varieties' identification in term of content of γ-OZ has become essential
- Baron, Giovanna,Fumagalli, Laura,Mazzotta, Sarah
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- A Series of Ferulic Acid Amides Reveals Unexpected Peroxiredoxin 1 Inhibitory Activity with in vivo Antidiabetic and Hypolipidemic Effects
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Insulin resistance is a major pathophysiological feature in the development of type 2 diabetes (T2DM). Ferulic acid is known for attenuating the insulin resistance and reducing the blood glucose in T2DM rats. In this work, we designed and synthesized a library of new ferulic acid amides (FAA), which could be considered as ring opening derivatives of the antidiabetic PPARγ agonists Thiazolidinediones (TZDs). However, since these compounds displayed weak PPAR transactivation capacity, we employed a proteomics approach to unravel their molecular target(s) and identified the peroxiredoxin 1 (PRDX1) as a direct binding target of FAAs. Interestingly, PRDX1, a protein with antioxidant and chaperone activity, has been implied in the development of T2DM by inducing hepatic insulin resistance. SPR, mass spectrometry-based studies, docking experiments and in vitro inhibition assay confirmed that compounds VIe and VIf bound PRDX1 and induced a dose-dependent inhibition. Furthermore, VIe and VIf significantly improved hyperglycemia and hyperlipidemia in streptozotocin-nicotinamide (STZ-NA)-induced diabetic rats as confirmed by histopathological examinations. These results provide guidance for developing the current FAAs as new potential antidiabetic agents.
- Yasmin, Sabina,Cerchia, Carmen,Badavath, Vishnu Nayak,Laghezza, Antonio,Dal Piaz, Fabrizio,Mondal, Susanta K.,Atl?, ?zlem,Baysal, Merve,Vadivelan, Sankaran,Shankar,Siddique, Mohd Usman Mohd,Pattnaik, Ashok Kumar,Singh, Ravi Pratap,Loiodice, Fulvio,Jayaprakash, Venkatesan,Lavecchia, Antonio
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p. 484 - 498
(2020/11/02)
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- Design, synthesis, and bioassay of 4-thiazolinone derivatives as influenza neuraminidase inhibitors
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A series of 4-thiazolinone derivatives (D1-D58) were designed and synthesized. All of the derivatives were evaluated in vitro for neuraminidase (NA) inhibitory activities against influenza virus A (H1N1), and the inhibitory activities of the five most pot
- Xiao, Mengwu,Xu, Lvjie,Lin, Ding,Lian, Wenwen,Cui, Manying,Zhang, Meng,Yan, Xiaowei,Li, Shuishi,Zhao, Jun,Ye, Jiao,Liu, Ailin,Hu, Aixi
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- Ferulic acid amide derivative, and synthesis method and application thereof
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The invention provides a ferulic acid amide derivative represented by the following general formula IV, wherein R represents phenyl, p-methoxyphenyl, 4-aminodiphenyl ether, 4-trifluoromethoxyphenyl, 4-(trifluoromethyl)phenyl, 3-aminobenzene isopropyl ethe
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Paragraph 0022-0024
(2021/06/13)
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- Quorum sensing and nf-κb inhibition of synthetic coumaperine derivatives from piper nigrum
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Bacterial communication, termed Quorum Sensing (QS), is a promising target for virulence attenuation and the treatment of bacterial infections. Infections cause inflammation, a process regulated by a number of cellular factors, including the transcription Nuclear Factor kappa B (NF-κB); this factor is found to be upregulated in many inflammatory diseases, including those induced by bacterial infection. In this study, we tested 32 synthetic derivatives of coumaperine (CP), a known natural compound found in pepper (Piper nigrum), for Quorum Sensing Inhibition (QSI) and NF-κB inhibitory activities. Of the compounds tested, seven were found to have high QSI activity, three inhibited bacterial growth and five inhibited NF-κB. In addition, some of the CP compounds were active in more than one test. For example, compounds CP-286, CP-215 and CP-158 were not cytotoxic, inhibited NF-κB activation and QS but did not show antibacterial activity. CP-154 inhibited QS, decreased NF-κB activation and inhibited bacterial growth. Our results indicate that these synthetic molecules may provide a basis for further development of novel therapeutic agents against bacterial infections.
- Baruch, Yifat,Gopas, Jacob,Kadosh, Yael,Kumar, Rajendran Saravana,Kushmaro, Ariel,Muthuraman, Subramani,Yaniv, Karin
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- Design, synthesis of Cinnamyl-paeonol derivatives with 1, 3-Dioxypropyl as link arm and screening of tyrosinase inhibition activity in vitro
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This study aimed to obtain tyrosinase inhibitors for treating hyperpigmentation. A series of cinnamyl ester analogues were designed and synthesized with cinnamic acid (CA) and peaonol compounds. The safety, melanin content and inhibitory effects of all ta
- Tang, Kai,Jiang, Yi,Zhang, Huawei,Huang, Wenli,Xie, Yundong,Deng, Chong,Xu, Hongbo,Song, Xiaomei,Xu, Hong
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- Thiourea derivatives, and preparation method and application thereof
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The invention relates to thiourea derivatives represented by formula I, pharmaceutically acceptable salts thereof and a pharmaceutical composition thereof, and an application of the thiourea derivatives in the preparation of an influenza virus neuraminida
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Paragraph 0042-0045
(2020/06/05)
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- Cinnamate derivatives and application of cinnamate derivatives as tyrosinase inhibitors and gels
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The invention discloses cinnamate derivatives and application of the cinnamate derivatives as tyrosinase inhibitors and gels, and the structural general formula of the cinnamate derivatives is shown in the specification, in the formula, X and Y independently represent any one of O, S and NH, wherein R1 and R2 independently represent any one of H, OH, methoxy, allyl and acetyl; R3 and R4 respectively and independently represent any one of H, OH, methoxy, tert-butyl dimethyl siloxy and carbethoxy, and R3 and R4 are not tert-butyl dimethyl silyl at the same time; and n is an integer from 2 to 5.The cinnamate derivatives disclosed by the invention have obvious inhibitory activity on the activity of mushroom tyrosinase diphenolic enzyme and the content of tyrosinase and melanin in melanoma cells of B16F10 mice, and can be used for preparing the tyrosinase inhibitors. Meanwhile, the cinnamate derivatives can form stable gels in olive oil and can be used as micromolecular gels for cosmeticsand the like.
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Paragraph 0077-0079; 0081
(2020/08/02)
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- Construction of 3D Antioxidants with Nucleosides as the Core: Inhibition of DNA Oxidation
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We herein attach ferulic and caffeic acids to -OH and -NH2 in cytidine, uridine, adenosine, or guanosine for achieving antioxidative hybrids with three-dimensional (3D) configuration. In the case of molecular docking computation, the nucleoside
- Zhao, Peng-Fei,Liu, An,Wei, Ming-Guang,Liu, Zai-Qun
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p. 15854 - 15864
(2019/12/25)
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- Design and synthesis novel di-carbonyl analogs of curcumin (DACs) act as potent anti-inflammatory agents against LPS-induced acute lung injury (ALI)
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A novel series of di-carbonyl analogs of curcumin (DACs) were prepared and evaluated for their anti-inflammatory properties. Preliminary results showed that a vast majority of compounds tested in this study could effectively suppress LPS-induced production of tumor necrosis factor (TNF)-α and interleukin (IL)-6. Structure-activity relationships of the compounds were discussed. Compounds 5a27 and 5a28 showed the most potent anti-inflammatory activities and had higher structural stability and orally bioavailability than curcumin in vitro. Mechanistically, they inhibited the activation of macrophages via the blockade of mitogen-activated protein kinase (MAPK) signaling and nuclear translocation of NF-κB. In vivo, 5a27 and 5a28 markedly alleviated lipopolysaccharides (LPS)-induced acute lung injury (ALI). The wet/dry ratio of lungs was significantly normalized by the active compounds, which was consistent with the suppression of neutrophil infiltration and production of proinflammatory cytokines. Collectively, these results present a new series of curcumin analogs as promising anti-inflammatory agents for treatment of ALI.
- Qian, Jianchang,Chen, Xianxin,Shu, Sheng,Zhang, Wenxin,Fang, Bo,Chen, Xiaojing,Zhao, Yunjie,Liu, Zhiguo,Liang, Guang
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p. 414 - 425
(2019/02/19)
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- Dual-carbonyl curcumin derivative and application thereof
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The invention discloses a dual-carbonyl curcumin derivative. The structure of the dual-carbonyl curcumin derivative is shown in the formula (1), according to the formula (1), the R substituent group is selected from alkoxy, halogen or other electrondrawin
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Paragraph 0023; 0024; 0028; 0029
(2019/04/26)
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- A caffeic acid-ferulic acid hybrid compound attenuates lipopolysaccharide-mediated inflammation in BV2 and RAW264.7 cells
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In the present study, we synthesized and evaluated the anti-inflammatory effects of the two component hybrids, caffeic acid (CA)-ferulic acid (FA), FA-Tryptamine (Trm), CA-Piperonyl Triazol (PT) and FA-PT. Of these five hybrids, CA-FA had the most potent
- Kwon, Mi-Youn,Kim, Sang-Min,Park, Jiwon,Lee, JuWon,Cho, Hyeongjin,Lee, Haneul,Jeon, Cheolmin,Park, Jeong-Ho,Han, Inn-Oc
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p. 565 - 571
(2019/06/27)
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- Regioselective synthesis of 7-O-esters of the flavonolignan silibinin and SARs lead to compounds with overadditive neuroprotective effects
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A series of neuroprotective hybrid compounds was synthesized by conjugation of the flavonolignan silibinin with natural phenolic acids, such as ferulic, cinnamic and syringic acid. Selective 7-O-esterfication without protection groups was achieved by appl
- Schramm, Simon,Huang, Guozheng,Gunesch, Sandra,Lang, Florian,Roa, Judit,H?gger, Petra,Sabaté, Raimon,Maher, Pamela,Decker, Michael
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supporting information
p. 93 - 107
(2018/02/15)
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- Preparation of ferulic acid dimer derivative and application of ferulic acid dimer derivative to treatment of Alzheimer's disease
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The invention discloses a ferulic acid dimer derivative and a preparation method thereof. Modification is carried out on the structural foundation of a natural lead compound ferulic acid; the preparedferulic acid derivative keeps the capability of elimina
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Paragraph 0020; 0021; 0026; 0027; 0028
(2018/07/30)
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- Synthesis of a series of benzothiazole amide derivatives and their biological evaluation as potent hemostatic agents
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A series of benzothiazole amide derivatives were synthesized through a facile and efficient method via a nucleophilic acyl substitution reaction between 2-aminobenzothiazole and various cinnamic acid compounds. The obtained products exhibited good thermal stabilities. All compounds were evaluated for their in vitro hemostatic activities using the commercially available standard drug etamsylate as a positive control. The results showed that compound Q2 had a significant partial coagulation activity, reduced capillary permeability at 5, 10 and 50 μmol L-1, activated thrombin activity, and a more potent platelet aggregation activity than the positive control group (etamsylate, up to 1283.9 times in the nanomole range). A molecular modeling study revealed that compound Q2 was a competitive thrombin activator. Therefore, Q2 may be a potential lead for further biological screening and for the generation of drug molecules. Moreover, the structure-activity relationship of the prepared compounds is also discussed herein.
- Nong, Wenqian,Zhao, Anran,Wei, Jinrui,Cheng, Hui,Luo, Xuan,Lin, Cuiwu
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p. 6231 - 6241
(2018/02/19)
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- Study on the anticoagulant or procoagulant activities of type II phenolic acid derivatives
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In this study, three type II phenolic acids (caffeic acid, p-hydroxycinnamic acid, and ferulic acid) were used to synthesize a total of 18 phenolic acid derivatives. With molecular docking for molecule design and target protein (factors) screening, in combination with the confirmation of target proteins (factors) by surface plasmon resonance, and the evaluation of haemostatic and anticoagulant activities with five blood assays (plasma recalcification time, prothrombin time, activated partial thromboplastin time, fibrinogen, and thrombin time), the data indicated that caffeic acid derivatives showed certain anticoagulant or procoagulant activities and that two other series contained compounds with the best anticoagulant activities. Using Materials Studio analysis, particular functional groups that affect anticoagulant or procoagulant activities were revealed, and these conclusions can guide the discovery of compounds with better activities.
- Luo, Xuan,Du, Chuanrong,Cheng, Hui,Chen, Jian-hua,Lin, Cuiwu
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- Synthesis and biological evaluation of a new series of cinnamic acid amide derivatives as potent haemostatic agents containing a 2-aminothiazole substructure
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Ten new cinnamic acid derivatives containing a 2-aminothiazole substructure were designed and synthesized. This series of compounds exhibited good thermostabilities as demonstrated by thermogravimetric analysis. In coagulation assays (prothrombin time, activated partial thromboplastin time and thrombin time) in vitro, most compounds demonstrated excellent activities to promote blood coagulation. Among the studied series, compounds N1, N4, N5 and W5 exhibited a significant coagulation activity. Further studies indicated that compound N5 (IC50 = 1.87 μmol/L) displayed the most suitable efficacy of promoting platelet aggregation than the clinically used haemostatic drug etamsylate (IC50 = 46.22 μmol/L). Furthermore, the relationship between the functional groups of the compounds and the corresponding blood coagulant activity was explored in this study.
- Nong, Wenqian,Zhao, Anran,Wei, Jinrui,Lin, Xiao,Wang, Lisheng,Lin, Cuiwu
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p. 4506 - 4511
(2017/09/12)
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- Enantioselective Organocatalytic Intramolecular Aza-Diels–Alder Reaction
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A highly efficient catalytic enantioselective intramolecular Povarov reaction was developed with primary anilines as 2-azadiene precursors. A wide variety of angularly fused azacycles were obtained without column chromatography in high to excellent yields and with excellent diastereo- and enantioselectivity (d.r.>99:1 and up to e.r. 99:1). Furthermore, the catalyst loading could be lowered to 1 mol %, and the obtained azacycles could be used as key intermediates for further transformations to generate additional molecular diversity.
- Jarrige, Lucie,Blanchard, Florent,Masson, Géraldine
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p. 10573 - 10576
(2017/08/22)
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- Novel ferulic amide derivatives with tertiary amine side chain as acetylcholinesterase and butyrylcholinesterase inhibitors: The influence of carbon spacer length, alkylamine and aromatic group
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Based on our recent investigations on chalcone derivatives as AChE inhibitors, a series of ferulic acid (FA) tertiary amine derivatives similar to chalcone compounds were designed and synthesized. The results of bioactivity evaluation revealed that most of new synthesized compounds had comparable or more potent AChE inhibitory activity than the control drug Rivastigmine. The alteration of carbon chain linking tertiary amine groups and ferulic acid scaffold markedly influenced the inhibition activity against AChE. Among them the inhibitory activity of compound 6d (IC50: 0.71 ± 0.09 μmol/L) and 6e (IC50: 1.11 ± 0.17 μmol/L) was equal to 15-fold and 9-fold than that of Rivastigmine against AChE (IC50: 10.54 ± 0.86 μmol/L), respectively. Moreover, compound 6d shows the highest selectivity for AChE over butyrylcholinesterase(BuChE) (ratio: 18.3). The kinetic study suggested that compound 6d revealed a mixed-type inhibition against AChE. The result of molecular docking showed that compound 6d combines to AChE with three amino acid sites(Trp84, Tyr334 and Trp279), while combines to BuChE with two amino acid sites (Tyr67 and Gly66) in enzyme domains, respectively. Compound 6d might act as a potential agent for the treatment of Alzheimer's diseases (AD).
- Liu, Haoran,Liu, Linbo,Gao, Xiaohui,Liu, Yingzi,Xu, Wanjun,He, Wei,Jiang, Hong,Tang, Jingjing,Fan, Haoqun,Xia, Xinhua
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p. 810 - 822
(2016/12/18)
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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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- Tetrahydroisoquinoline compound, preparation method and anti-tumor use
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The invention relates to the field of medicinal chemistry, and in particular relates to a tetrahydroisoquinoline compound with a general formula I or II, a preparation method as well as a pharmaceutical composition and an application thereof. Pharmacodyna
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- Preparation method of avenanthramide and derivative thereof
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The invention provides a preparation method of avenanthramide and a derivative thereof. The avenanthramide and the derivative thereof are synthesized and obtained by mainly utilizing an organic acid and aminobenzoic acid as major reactants. The method is
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Paragraph 0021
(2017/08/19)
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- Monoamine Oxidase Inhibitory Activity of Ferulic Acid Amides: Curcumin-Based Design and Synthesis
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Ferulic acid has structural similarity with curcumin which is being reported for its monoamine oxidase (MAO) inhibitory activity. Based on this similarity, we designed a series of ferulic acid amides 6a-m and tested for their inhibitory activity on human MAO (hMAO) isoforms. All the compounds were found to inhibit the hMAO isoforms either selectively or non-selectively. Nine compounds (6a, 6b, 6g-m) were found to inhibit hMAO-B selectively, whereas the other four (6c-f) were found to be non-selective. There is a gradual shift from hMAO-B selectivity (6a,b) to non-selectivity (6c-f) as there is an increase in chain length at the amino terminus. In case of compounds having an aromatic nucleus at the amino terminus, increasing the carbon number between N and the aromatic ring increases the potency as well as selectivity toward hMAO-B. Compounds 6f, 6j, and 6k were subjected to membrane permeability and metabolic stability studies by in vitro assay methods. They were found to have a better pharmacokinetic profile than curcumin, ferulic acid, and selegiline. In order to understand the structural features responsible for the potency and selectivity of 6k, we carried out a molecular docking simulation study.
- Badavath, Vishnu N.,Baysal, Ipek,Uar, Gülberk,Mondal, Susanta K.,Sinha, Barij N.,Jayaprakash, Venkatesan
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- NOVEL KOJIC ACID CONJUGATED COMPOUNDS AND THEIR BIOLOGICAL APPLICATIONS
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The present invention relates to a novel kojic acid conjugated compound conjugated by a click reaction of kojic acid and an antioxidant derivative, an antioxidant dietary supplement comprising the same, and a composition for external application on skin h
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Paragraph 0151-0154
(2016/10/10)
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- NOVEL TRYPTAMINE CONJUGATED COMPOUNDS AND THEIR BIOLOGICAL APPLICATIONS
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The present invention relates to a novel tryptamine conjugated compound obtained by conjugating tryptamine derivatives and antioxidant derivatives by a click reaction, and a pharmaceutical composition and a health supplement food composition for preventin
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Paragraph 0162; 0164
(2016/12/07)
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- Design, synthesis and "in vitro" anti-leukemic evaluation of ferulic acid analogues as BCR-Abl inhibitors
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Semi-synthetic modification of ferulic acid isolated from Salicornia brachiata was performed and the derivatives showed gratifying in silico binding scores with the BCR-Abl protein, comparable with imatinib. Anti-proliferative activity against K562, U937 and Hep G2 cancer cell lines and the BCR-Abl kinase inhibitory activity using an ADP-Glo assay were investigated. Compounds 2i and 3j were potent BCR-Abl inhibitors and were also active against K562 cells.
- Rajendran, Narendran,Subramaniam, Shankar,Charan Raja, Mamilla R.,Venkata Subbarao, Himesh Makala,Raghunandan, Subhashree,Venkatasubramanian, Ulaganathan,Pemaiah, Brindha,Mahapatra, Santanu Kar,Sivasubramanian, Aravind
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p. 70480 - 70484
(2016/08/06)
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- α-Glucosidase inhibitory activities of phenolic acid amides with l-amino acid moiety
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α-Glucosidase inhibitors can effectively control postprandial hyperglycemia. In this study, a series of phenolic acids with the l-amino acid moiety were synthesized and their inhibitory activities against α-glucosidase from Saccharomyces cerevisiae (EC 3.
- Liu, Bin,Ma, Ji-Mei,Chen, Hang-Wei,Li, Zi-Long,Sun, Lin-Hao,Zeng, Zhen,Jiang, Hong
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p. 50837 - 50845
(2016/06/09)
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- Design, synthesis, and biological evaluation of novel Tempol derivatives as effective antitumor agents
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Two series of novel Tempol derivatives T1–T6 based on the piperidine nitroxide Tempol and phenolic acids were designed and synthesized, and their biological evaluation is also described. The chemical structure was verified by HRMS, IR, and EPR analysis. The antitumor activity was tested against two tumor cell lines (A549 and Hela cells). Simultaneously, HK-2 cells were selected to investigate cytotoxicity and selectivity of synthetic compounds to the normal cells. The antioxidant property was also studied by DPPH radical scavenging assay and hydrogen peroxide-induced cell injury assay. The results demonstrated that most of the Tempol derivatives exhibited more active antioxidant activity than Tempol, and all synthesized Tempol derivatives exhibited more potent antitumor activity than Tempol. Among them, compound T6 displayed the highest antitumor activity (IC50?=?29.4?μg/mL for A549 cells; IC50?=?16.2?μg/mL for Hela cells). The results indicated that T6 exhibited efficient antitumor performance, having the potential of being excellent antitumor agents for cancer treatment.
- Sun, Xiao-Liang,Wang, Shi-Yu,Qi, Zhi-Min,Wan, Ning,Zhang, Bang-Le,He, Wei
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p. 7659 - 7673
(2016/09/20)
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- Compound formed by combining ferulic acid with asarone analogue as well as preparation method and application of compound
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The invention belongs to the technical field of medicines and discloses a compound formed by combining ferulic acid with an asarone analogue as well as a preparation method and an application of the compound. The structure of the compound is shown in the
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- p-Coumaroyl-CoA:Monolignol Transferase
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The invention relates to nucleic acids encoding a p-coumaroyl-CoA:monolignol transferase and to inhibitory nucleic acids adapted to inhibit the expression and/or translation of a p-coumaroyl-CoA:monolignol transferase RNA. Inhibition of p-coumaroyl-CoA:monolignol transferase in plants improves the incorporation of monolignol ferulates into the lignin of plants, giving rise to plant biomass that is more easily processed into useful products such as paper and biofuels.
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Paragraph 0282
(2016/03/13)
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- Synthesis of hydroxyethyl starch derivatives with phenylpropanoid fragments attached through ester or sulfide bonds
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Approaches to the synthesis of hydroxyethyl starch derivatives containing phenylpropanoic acid fragments with various degree of substitution were suggested. Esterification of hydroxyethyl starch in heterogeneous aqueous organic medium gave rise to the cor
- Torlopov,Udoratina,Belyaev
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p. 2130 - 2135
(2015/06/08)
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- Synthesis, cytotoxicity and molecular modelling studies of new phenylcinnamide derivatives as potent inhibitors of cholinesterases
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The present study reports the synthesis of cinnamide derivatives and their biological activity as inhibitors of both cholinesterases and anticancer agents. Controlled inhibition of brain acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) may slow neurodegeneration in Alzheimer's diseases (AD). The anticholinesterase activity of phenylcinnamide derivatives was determined against Electric Eel acetylcholinesterase (EeAChE) and horse serum butyrylcholinesterase (hBChE) and some of the compounds appeared as moderately potent inhibitors of EeAChE and hBChE. The compound 3-(2-(Benzyloxy)phenyl)-N- (3,4,5-trimethoxyphenyl)acrylamide (3i) showed maximum activity against EeAChE with an IC50 0.29 ± 0.21 μM whereas 3-(2-chloro-6- nitrophenyl)-N-(3,4,5-trimethoxyphenyl)acrylamide (3k) was proved to be the most potent inhibitor of hBChE having IC50 1.18 ± 1.31 μM. To better understand the enzyme-inhibitor interaction of the most active compounds toward cholinesterases, molecular modelling studies were carried out on high-resolution crystallographic structures. The anticancer effects of synthesized compounds were also evaluated against cancer cell line (lung carcinoma). The compounds may be useful leads for the design of a new class of anticancer drugs for the treatment of cancer and cholinesterase inhibitors for Alzheimer's disease (AD).
- Saeed, Aamer,Mahesar, Parvez Ali,Zaib, Sumera,Khan, Muhammad Siraj,Matin, Abdul,Shahid, Mohammad,Iqbal, Jamshed
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- Structure-activity relationships of glycogen phosphorylase inhibitor FR258900 and its analogues: A combined synthetic, enzyme kinetics, and computational study
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A series of O- or N-cinnamoylated, p-coumaroylated, feruloylated, phenyl, and substituted phenylpropiolated derivatives of lmalic, 3-hydroxypentanedioic, and l-glutamic acids were synthesized as analogues of the natural product glycogen phosphorylase (GP) inhibitor FR258900 (2,3-bis(4-hydroxycinnamoyloxy) glutaric acid). These compounds proved practically inactive against rabbit muscle glycogen phosphorylase b. A structure-activity study involving previously synthesized tartaric acid analogues of FR258900 revealed that two acyl moieties must be present in the compounds to make a good inhibitor. Molecular modeling methods (docking and quantitative structure-activity relationship (QSAR) calculations) were used to understand the nature of the binding affinities of these GP inhibitors. The generated 3D models for GP-inhibitor complexes showed that both the polar allosteric site pocket and the hydrophobic pocket at the interface of the homodimeric units of GP were important for effective binding of the acyl and aromatic moieties of the inhibitors. The predictive QSAR models consist of empirical and quantum mechanics descriptors and provide good explanatory and predictive abilities (prediction coefficient Q2=0.7-0.9 when cross-validation procedures were performed).
- Juhsz, Lszl,Varga, Gergely,Sztankovics, Andrea,Bke, Ferenc,Docsa, Tibor,Kiss-Szikszai, Attila,Gergely, Pl,Ka, Juraj,Tvaroka, Igor,Somsk, Lszl
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p. 1558 - 1568
(2015/02/05)
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- Structure-Activity Relationships of Glycogen Phosphorylase Inhibitor FR258900 and Its Analogues: A Combined Synthetic, Enzyme Kinetics, and Computational Study
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A series of O- or N-cinnamoylated, p-coumaroylated, feruloylated, phenyl, and substituted phenylpropiolated derivatives of L-malic, 3-hydroxypentanedioic, and L-glutamic acids were synthesized as analogues of the natural product glycogen phosphorylase (GP) inhibitor FR258900 (2,3-bis(4-hydroxycinnamoyloxy)glutaric acid). These compounds proved practically inactive against rabbit muscle glycogen phosphorylase b. A structure-activity study involving previously synthesized tartaric acid analogues of FR258900 revealed that two acyl moieties must be present in the compounds to make a good inhibitor. Molecular modeling methods (docking and quantitative structure-activity relationship (QSAR) calculations) were used to understand the nature of the binding affinities of these GP inhibitors. The generated 3D models for GP-inhibitor complexes showed that both the polar allosteric site pocket and the hydrophobic pocket at the interface of the homodimeric units of GP were important for effective binding of the acyl and aromatic moieties of the inhibitors. The predictive QSAR models consist of empirical and quantum mechanics descriptors and provide good explanatory and predictive abilities (prediction coefficient Q2=0.7-0.9 when cross-validation procedures were performed).
- Juhsz, Lszl,Varga, Gergely,Sztankovics, Andrea,Bke, Ferenc,Docsa, Tibor,Kiss-Szikszai, Attila,Gergely, Pl,Ka, Juraj,Tvaroka, Igor,Somsk, Lszl
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p. 1558 - 1568
(2015/08/24)
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- Syntheses of 3-, 4-, and 5-O-feruloylquinic acids
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The efficient synthesis of 3-, 4-, and 5-O-feruloylquinic acids starting from d-(-)-quinic acid is described. Esterification of suitably protected quinic acid derivatives with 3-(4-acetoxy-3-methoxyphenyl)-acryloyl chloride and subsequent hydrolysis of al
- Dokli, Irena,Navarini, Luciano,Hamersak, Zdenko
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p. 785 - 790
(2013/08/23)
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- Chemical and microbial semi-synthesis of tetrahydroprotoberberines as inhibitors on tissue factor procoagulant activity
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To discover new inhibitors on tissue factor procoagulant activity, 21 tetrahydroprotoberberines were screened on the model of human THP-1 cells stimulated by lipopolysaccharide. Among these tetrahydroprotoberberines, several unique compounds were synthesized through microbial transformation: compound 6 (l-corydalmine) was obtained through regio-selective demethylation by Streptomyces griseus ATCC 13273, whereas compounds 4a, 4b, 5h, and 5i were microbial glycosylation products by Gliocladium deliquescens NRRL1086. The bioassay results showed that compounds 3 (tetrahydroberberine), 10 (tetrahydroberberrubine), and 5f (cinnamyl ester of 5) and 5i (glycosidic product of 5), exhibited the most potential effects, with IC50 values of 8.35, 6.75, 3.75, and 8.79 nM, respectively. The preliminary structure and activity relationship analysis revealed that the 2,3-methylenedioxy group of the A ring was essential for the strong inhibitory effects, and the R configuration of the chiral center C-14 showed higher activity than S-form products. The formation of fatty acid or aromatic acid esters of compound 5, except the cinnamyl esters, would weaken its effects. It is also interesting to note that the glycosylation of tetrahydroprotoberberines will maintain and even enhance the inhibitory effects. Because of the importance of glycochemistry in new drug discovery and development, this deserves further exploration and may provide some guide on the semi-synthesis of tetrahydroprotoberberines as tissue factor pathway inhibitors. Our findings also provide some potential leading compounds for tissue factor-related diseases, such as cancer and cardiovascular diseases.
- Ge, Hai-Xia,Zhang, Jian,Chen, Ling,Kou, Jun-Ping,Yu, Bo-Yang
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- Preparation of monolignol γ-acetate, γ-p-hydroxycinnamate, and γ-p-hydroxybenzoate conjugates: Selective deacylation of phenolic acetates with hydrazine acetate
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We report here a reliable and facile synthesis of a range of monolignol γ-p-hydroxycinnamate (including p-coumarate, ferulate, and caffeate), γ-acetate, and γ-p-hydroxybenzoate conjugates, many not previously reported, that are either putative intermediat
- Zhu, Yimin,Regner, Matthew,Lu, Fachuang,Kim, Hoon,Mohammadi, Allison,Pearson, Timothy J.,Ralph, John
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p. 21964 - 21971
(2013/11/06)
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- Novel adenosine A2A receptor ligands: A synthetic, functional and computational investigation of selected literature adenosine A2A receptor antagonists for extending into extracellular space
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Growing evidence has suggested a role in targeting the adenosine A 2A receptor for the treatment of Parkinson's disease. The literature compounds KW 6002 (2) and ZM 241385 (5) were used as a starting point from which a series of novel ligands targeting the adenosine A2A receptor were synthesized and tested in a recombinant human adenosine A2A receptor functional assay. In order to further explore these molecules, we investigated the biological effects of assorted linkers attached to different positions on selected adenosine A2A receptor antagonists, and assessed their potential binding modes using molecular docking studies. The results suggest that linking from the phenolic oxygen of selected adenosine A2A receptor antagonists is relatively well tolerated due to the extension towards extracellular space, and leads to the potential of attaching further functionality from this position.
- J?rg, Manuela,Shonberg, Jeremy,Mak, Frankie S.,Miller, Neil D.,Yuriev, Elizabeth,Scammells, Peter J.,Capuano, Ben
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p. 3427 - 3433
(2013/06/26)
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- Synthesis and anti-angiogenetic activity evaluation of N-(3-aryl acryloyl)aminosaccharide derivatives
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In order to find novel potent inhibitors for signal pathways of FGF/FGFR, nineteen N-(3-aryl acryloyl)aminosaccharide derivatives were designed and synthesized based on the binding sites of FGF and oligosaccharides of heparin. Their structures were confirmed by IR, 1H NMR, 13C NMR, MS and elemental analysis. The nineteen target compounds were evaluated for biological activity against HUVEC cell. In vitro assays showed that compound 10s (IC50 = 5.3 μM) exhibited comparable inhibitory effects on endothelial cell growth with topotecan (IC50 = 2.7 μM). Compound 10s (10 μg/egg) also showed obvious anti-angiogenetic activity in the in vivo chicken chorio allantoic membrane (CAM) assay, and the potency was similar to topotecan (10 μg/egg).
- Liu, Kun,Yao, Shuowei,Lou, Yinghan,Xu, Yungen
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- Bidirectional synthesis of montamine analogs
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Reported herein is a bidirectional synthesis of symmetric N,N′-diacyl hydrazide compounds closely resembling the alkaloid natural product montamine. In the process, di-tert-butyl hydrazine-1,2-dicarboxylate was smoothly dialkylated with alkyl halides, then Boc deprotected and acylated with an acetate-protected acid chloride derived from ferulic acid. After acetate removal, simple montamine analogs were obtained in excellent overall yields. Fischer indole synthesis with 4-methoxyphenylhydrazine hydrochloride and dihydrofuran provided 5-methoxytryptophol, which was then elaborated to the 1,2-bis(5-methoxyindol-3-yl)hydrazide structure bearing the substitution pattern found in montamine.
- Freitas, Melanie B.,Simollardes, Kelly A.,Rufo, Caroline M.,McLellan, Chantel N.,Dugas, Gabrielle J.,Lupien, Leslie E.,Davie, Elizabeth A. Colby
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supporting information
p. 5489 - 5491
(2013/09/23)
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- The design, synthesis and in vitro immunosuppressive evaluation of novel isobenzofuran derivatives
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The synthesis and biological evaluation of a series of novel isobenzofuran-based compounds are described. The compounds were evaluated for their immunosuppressive effects of T-cell proliferation and IMPDH type II inhibitor activity in vitro, as well as their structure-activity relationships were assessed. Several compounds demonstrated highly efficacious immunosuppressive properties, especially compounds 2d, 2e, 2h and 2j, which were superior to MPA, while compounds 2k, 2m, 2n, 4c and 5d exhibited an equipotent inhibitory activity compared to MPA. Generally, it was obviously demonstrated that α,β-unsaturated amides proved more potent than the diamide and urea series. The present study provides a guide for further research on development of safe and effective immunosuppressive agents.
- Yang, Na,Wang, Qing-He,Wang, Wen-Qian,Wang, Jian,Li, Feng,Tan, Shen-Peng,Cheng, Mao-Sheng
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scheme or table
p. 53 - 56
(2012/02/16)
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- Simultaneous analysis of free phytosterols/phytostanols and intact phytosteryl/phytostanyl fatty acid and phenolic acid esters in cereals
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An approach based on solid-phase extraction for the effective separation of free phytosterols/phytostanols and phytosteryl/phytostanyl fatty acid and phenolic acid esters from cereal lipids was developed. The ester conjugates were analyzed in their intact
- Esche, Rebecca,Barnsteiner, Andreas,Scholz, Birgit,Engel, Karl-Heinz
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p. 5330 - 5339
(2012/09/07)
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- Synthesis and antiproliferative activity of helonioside A, 3′,4′,6′-tri-O-feruloylsucrose, lapathoside C and their analogs
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The first total synthesis of natural phenylpropanoid sucrose esters (PSEs) helonioside A 1, 3′,4′,6′-tri-O-feruloylsucrose 2 and lapathoside C 3 along with 17 unnatural PSE analogs has been successfully accomplished in a short and simple synthetic route.
- Panda, Parthasarathi,Appalashetti, Manjuvani,Natarajan, Meenubharathi,Mary, Chan-Park,Venkatraman, Subbu S.,Judeh, Zaher M.A.
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p. 418 - 430
(2013/02/23)
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- Synthesis, antioxidant and antimicrobial evaluation of simple aromatic esters of ferulic acid
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Aromatic ester derivatives of ferulic acid where the phenolic hydroxyl is free (6a-d) or acetylated (5a-d) were evaluated for their antioxidant and antimicrobial properties. The superoxide radical scavenging capacity of compounds 5d and 6d-e (IC50 of 0.19, 0.27 and 0.20 mM, respectively) was found to be twice as active as a-tocopherol (IC50 = 0.51 mM). DPPH radical scavenging capacity was moderate and only found in compounds bearing free phenolic hydroxyl groups (6a-e). With regard to antimicrobial properties, compounds 6b and 6c displayed significant activity against Enterococcus faecalis (MICs = 16 μg/mL) and vancomycin-resistant E. faecalis (MIC for 6b, 32 and for 6c, 16 μg/mL). Compound 6c also demonstrated prominent activity against planktonic Staphylococcus aureus with a MIC value of 8 μg/mL and it inhibited bacterial biofilm formation by S. aureus with a MBEC value of 8 μg/mL, which was 64 and 128 times more potent than ofloxacin and vancomycin, respectively.
- Erguen, Burcu Caliskan,Coban, Tuelay,Onurdag, Fatma Kaynak,Banoglu, Erden
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experimental part
p. 1251 - 1261
(2012/05/20)
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- Selective butyrylcholinesterase inhibitors using polyphenol-polyphenol hybrid molecules
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Polyphenols (PPs) are known as antioxidant compounds having benign biological activities. In this paper, a series of hybrid molecules between the free or acetyl protected polyphenol compounds were synthesized and their in vitro antioxidant activity (DPPH
- Woo, Yeun Ji,Lee, Bo Hyun,Yeun, Go Heum,Kim, Hyun Ju,Won, Moo-Ho,Kim, Sang Hern,Lee, Bong Ho,Park, Jeong Ho
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body text
p. 2593 - 2598
(2012/01/19)
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- How to distinguish between feruloyl quinic acids and isoferuloyl quinic acids by liquid chromatography/tandem mass spectrometry
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All four regioisomers of feruloyl quinic acid and isoferuloyl quinic acid were synthesized and a liquid chromatography/tandem mass spectrometry (LC/MS/MS) method developed that resolves all eight regioisomers. All eight regioisomers can be readily disting
- Kuhnert, Nikolai,Jaiswal, Rakesh,Matei, Marius Febi,Sovdat, Tina,Deshpande, Sagar
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experimental part
p. 1575 - 1582
(2011/11/06)
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- Amide-containing diketoacids as HIV-1 integrase inhibitors: Synthesis, structure-activity relationship analysis, and biological activity
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HIV-1 integrase, which catalyzes the integration of the viral genome into the cellular chromosome, is an essential enzyme for retroviral replication, and represents an attractive and validated target in the development of therapeutics against AIDS. In this paper, 17 amide-containing novel diketoacids were designed and synthesized, and their ability to inhibit HIV-1 integrase was tested. The structure-activity relationships were also analyzed.
- Li, Hongcai,Wang, Chao,Sanchez, Tino,Tan, Yanmei,Jiang, Chunying,Neamati, Nouri,Zhao, Guisen
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experimental part
p. 2913 - 2919
(2009/09/06)
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