- Sevanol and its analogues: Chemical synthesis, biological effects and molecular docking
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Among acid-sensing ion channels (ASICs), ASIC1a and ASIC3 subunits are the most widespread and prevalent in physiological and pathophysiological conditions. They participate in synaptic plasticity, learning and memory, as well as the perception of inflamm
- Belozerova, Olga A.,Osmakov, Dmitry I.,Vladimirov, Andrey,Koshelev, Sergey G.,Chugunov, Anton O.,Andreev, Yaroslav A.,Palikov, Victor A.,Palikova, Yulia A.,Shaykhutdinova, Elvira R.,Gvozd, Artem N.,Dyachenko, Igor A.,Efremov, Roman G.,Kublitski, Vadim S.,Kozlov, Sergey A.
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Read Online
- Synthesis of novel caffeic acid derivatives and their protective effect against hydrogen peroxide induced oxidative stress via Nrf2 pathway
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Aim: This study was aimed to synthesize novel caffeic acid derivatives and evaluate their potential applications for the treatment of oxidative stress associated disease. Main methods: Caffeic acid sulfonamide derivatives were synthesized by coupling sulf
- Chai, Ling,Chen, Hailan,Huang, Kelin,Lin, Cuiwu,Natarajan, Bharathi,Peng, Xiaoyu,Wu, Gang,Yang, Songxin,Zhao, Anran
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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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- Novel 3C-like protease inhibitor as well as preparation method and application thereof
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The invention provides a novel 3C-like protease inhibitor which is 3 ", 4" - O - diacetyl -epicatechin trans-caffeic acid ester with a specific structure. The invention further provides a preparation method and application of the 3C-like protease inhibitor. The invention has the advantages that the compound 3 ", 4" - O - diacetyl - epicatechin trans-caffeic acid ester is designed and synthesized based on the structure of epicatechin; even when the concentration is low, the activity of 3C-like protease in the novel coronavirus can be obviously inhibited. The compounds can be used as 3C-like protease inhibitors and are used for preparing anti-novel coronavirus SARS-CoV - 2 infection drugs.
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Paragraph 0047-0048; 0057-0059
(2021/09/26)
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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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supporting information
(2020/12/13)
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- Synthesis of caffeic acid sulfonamide derivatives and their protective effect against H2O2 induced oxidative damage in A549 cells
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Exogenous antioxidants are considered as important therapeutic tools for oxidative stress associated disorders as they can regulate the redox state, which is associated with cell and organ function. Inspired by natural polyphenols, six new caffeic acid sulfonamide derivatives were synthesized by coupling sulfonamides to the backbone of caffeic acid with good yields. Their structure and lipophilicity were characterized by 1H nuclear magnetic resonance (NMR), 13C{1H} NMR, infrared spectroscopy (IR) and oil-water partition coefficient assay. Their free radical scavenging activity and antioxidant activity were assessed by DPPH assay and hydrogen peroxide (H2O2) induced oxidative stress in human lung carcinoma A549 cells. The oil-water partition coefficient results indicate that the conjugation of sulfonamides increases the lipophilicity of caffeic acid. The CASMD, CASDZ and CASN results show higher free radical scavenging effects compared with vitamin C. The derivatives do not show any inhibitory effect on the proliferation of A549 cells up to a concentration of 200 μM, except CASDZ which significantly inhibits the growth of A549 cells at a concentration of 200 μM. In addition, the obtained derivatives markedly attenuate H2O2 induced decrease of cell viability, inhibit the production of ROS and MDA, and promote the activities of superoxide dismutase (SOD), catalase (CAT) and glutathione peroxidase (GSH-Px). Besides, treatment of H2O2 stimulated A549 cells with caffeic acid sulfonamide derivatives further increases mRNA expression of NF-E2-related factor 2 (Nrf2) and its target genes, including heme oxygenase-1 (HO-1), NAD(P)H quinone dehydrogenase 1 (NQO1) and thioredoxin reductase 1 (TXNRD1). These results suggest that these new caffeic acid sulfonamide derivatives have higher lipophilicity and better antioxidant activities than the parent caffeic acid, and they might be able to control the antioxidant response in cells via the Nrf2 pathway.
- Chen, Hailan,Hu, Tingjun,Lin, Cuiwu,Natarajan, Bharathi,Peng, Xiaoyu,Wei, Jiata,Yan, Hao,Zhang, Yuxue,Zhao, Anran
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p. 9924 - 9933
(2020/03/23)
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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; 0091-0094
(2020/08/02)
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- Preparation method and application of hydroxyl cinnamyl ester type catechin
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The invention relates to a preparation method and application of hydroxyl cinnamyl ester type catechins. The hydroxyl cinnamyl ester type catechins comprise four catechins which are respectively namedas epicatechin trans-coumarate, epicatechin trans-caffeic acid ester, epigallocatechin trans-coumarate and epigallocatechin trans-caffeic acid ester. The hydroxyl cinnamyl ester type catechins are prepared by the following steps: carrying out four steps of full acetylation on epicatechin and epigallocatechin, removal of acetyl on phenolic hydroxyl, silanizing of phenolic hydroxyl and removal of 3-acetyl, then respectively esterifying with acetylated caffeic acid or coumaric acid acyl chloride, and removing a protecting group. The preparation method of the four catechins is simple and mild inconditions, and can be completed under general experimental conditions. The four hydroxycinnamyl ester type catechins have a certain inhibition effect on the activity of alpha-glucosidase, can be usedfor hypoglycemic drugs, and have important significance in the fields of agriculture and medicine.
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Paragraph 0065; 0071; 0089
(2020/06/24)
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- N-Cinnamoylanthranilates as human TRPA1 modulators: Structure-activity relationships and channel binding sites
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The transient receptor potential ankyrin 1 (TRPA1) channel is a non-selective cation channel, which detects noxious stimuli leading to pain, itch and cough. However, the mechanism(s) of channel modulation by many of the known, non-reactive modulators has not been fully elucidated. N-Cinnamoylanthranilic acid derivatives (CADs) contain structural elements from the TRPA1 modulators cinnamaldehyde and flufenamic acid, so it was hypothesized that specific modulators could be found amongst them and more could be learnt about modulation of TRPA1 with these compounds. A series of CADs was therefore screened for agonism and antagonism in HEK293 cells stably transfected with WT-human (h)TRPA1, or C621A, F909A or F944A mutant hTRPA1. Derivatives with electron-withdrawing and/or electron-donating substituents were found to possess different activities. CADs with inductive electron-withdrawing groups were agonists with desensitising effects, and CADs with electron-donating groups were either partial agonists or antagonists. Site-directed mutagenesis revealed that the CADs do not undergo conjugate addition reaction with TRPA1, and that F944 is a key residue involved in the non-covalent modulation of TRPA1 by CADs, as well as many other structurally distinct non-reactive TRPA1 ligands already reported.
- Chandrabalan, Arundhasa,McPhillie, Martin J.,Morice, Alyn H.,Boa, Andrew N.,Sadofsky, Laura R.
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supporting information
p. 141 - 156
(2019/03/17)
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- Caffeic acid esters are effective bactericidal compounds against paenibacillus larvae by altering intracellular oxidant and antioxidant levels
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American Foulbrood (AFB) is a deadly bacterial disease affecting pupal and larval honey bees. AFB is caused by the endospore-forming bacterium Paenibacillus larvae (PL). Propolis, which contains a variety of organic compounds, is a product of bee foraging and is a resinous substance derived from botanical substances found primarily in trees. Several compounds from the class of caffeic acid esters, which are commonly found in propolis, have been shown to have antibacterial activity against PL. In this study, six different caffeic acid esters were synthesized, purified, spectroscopically analyzed, and tested for their activity against PL to determine the minimum inhibitory concentrations (MICs) and minimum bactericidal concentrations (MBCs). Caffeic acid isopropenyl ester (CAIE), caffeic acid benzyl ester (CABE), and caffeic acid phenethyl ester (CAPE) were the most effective in inhibiting PL growth and killing PL cell with MICs and MBCs of 125 μg/mL when used individually, and a MIC and MBC of 31.25 μg/mL for each compound alone when CAIE, CABE, and CAPE are used in combination against PL. These compounds inhibited bacterial growth through a bactericidal effect, which revealed cell killing but no lysis of PL cells after 18 h. Incubation with CAIE, CABE, and CAPE at their MICs significantly increased reactive oxygen species levels and significantly changed glutathione levels within PL cells. Caffeic acid esters are potent bactericidal compounds against PL and eliminate bacterial growth through an oxidative stress mechanism.
- Collins, William,Lowen, Noah,Blake, David J.
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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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- Isolation, total synthesis and quantification of caffeoylisocitric acid, a characteristic ingredient of the superfood amaranth
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Amaranth is regarded as a new “super-vegetable” in western countries, albeit it is consumed for centuries in Africa and Asia. In addition to common carotenoids, flavonoids and polyphenols, caffeoylisocitric acid has been described as amaranth type-specifi
- Zhou, Tianyi,Ringbeck, Benedikt,Schebb, Nils Helge,Scherkenbeck, Jürgen
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p. 4479 - 4485
(2019/07/03)
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- Synthesis and anticancer activity evaluation of some new derivatives of 2-(4-benzoyl-1-piperazinyl)-quinoline and 2-(4-cinnamoyl-1-piperazinyl)-quinoline
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In this study, we designed and synthesized twenty new derivatives of 2-(4-benzoyl-1-piperazinyl)- quinoline and 2-(4-cinnamoyl-1-piperazinyl)-quinoline with potential anticancer activity. The structures of synthesized compounds were confirmed by 1H and 13C NMR spectroscopy and MS spectrometry. The activity of novel compounds was evaluated in the cell viability assay as well as in the wound healing assay. Presented data show that examined substances have anticancer activity in cell culture. Seven compounds which showed a high rate of cell growth inhibition were selected for further studies. Three of them strongly reduced the growth of B16F10 cells. The novel compounds constitute a good base for further studies and optimization of structure for new therapeutically effective anti-cancerous drugs.
- Kubica, Krzysztof P.,Taciak, Przemys?aw P.,Czajkowska, Agnieszka,Stokfisz-Ignasiak, Alicja,Wyrebiak, Rafa?,Podsadni, Piotr,M?ynarczuk-Bia?y, Izabela,Malejczyk, Jacek,Mazurek, Aleksander P.
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p. 891 - 901
(2018/09/25)
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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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- New Hydroxycinnamic Acid Esters as Novel 5-Lipoxygenase Inhibitors That Affect Leukotriene Biosynthesis
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Leukotrienes are inflammatory mediators that actively participate in the inflammatory response and host defense against pathogens. However, leukotrienes also participate in chronic inflammatory diseases. 5-lipoxygenase is a key enzyme in the biosynthesis
- Boudreau, Luc H.,Lassalle-Claux, Grégoire,Cormier, Marc,Blanchard, Sébastien,Doucet, Marco S.,Surette, Marc E.,Touaibia, Mohamed
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- Propylene acylated 1, 5 - diaryl - 1, 2, 4 - triazole derivatives, their preparation method and medical use
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The invention relates to an allylbenzene acylation 1,5-diaryl-1,2,4-triazole derivative, a preparation method of the allylbenzene acylation 1,5-diaryl-1,2,4-triazole derivative and a medicine purpose of the allylbenzene acylation 1,5-diaryl-1,2,4-triazole
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Paragraph 0222-0024
(2017/10/31)
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- Structure–activity relationship of caffeic acid phenethyl ester analogs as new 5-lipoxygenase inhibitors
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Leukotrienes (LTs) are a class of lipid mediators implicated in numerous inflammatory disorders. Caffeic acid phenethyl ester (CAPE) possesses potent anti-LTs activity through the inhibition of 5-lipoxygenase (5-LO), the key enzyme in the biosynthesis of LTs. In this study, we describe the design and synthesis of CAPE analogs as radical scavengers and 5-LO inhibitors. Caffeic esters bearing propargyl and allyl linkers between the caffeoyl and aryl moieties (4a–i and 5a–i, respectively) were synthesized by Sonogashira and Heck cross-coupling reactions to probe the effects of flexibility and aryl substitution on 5-LO inhibition. Caffeoyl alcohol and ethers (6, 7a–b) as well as caffeoyl aldehyde and ketones (8a–e) were synthesized to elucidate the importance of the ester linkage for inhibitory activity. All tested compounds proved to be good radical scavengers (IC50 of 10–30?μm). After preliminary anti-LTs activity screening in HEK293 cell models, 5-LO inhibition potential of selected compounds was determined in human polymorphonuclear leukocytes (PMNL). Most screened compounds outperformed CAPE 3 in concentration-dependent assays on PMNL, with ester dimers 4i and 5i along with caffeoyl ethers 7a–b being roughly eight-, seven-, and 16-fold more potent than Zileuton, with IC50 values of 0.36, 0.43, and 0.18?μm, respectively.
- Doiron, Jérémie A.,Leblanc, Luc M.,Hébert, Martin J. G.,Levesque, Natalie A.,Paré, Aurélie F.,Jean-Fran?ois, Jacques,Cormier, Marc,Surette, Marc E.,Touaibia, Mohamed
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p. 514 - 528
(2017/04/06)
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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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supporting information
p. 4506 - 4511
(2017/09/12)
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- Examination of α-exosite inhibitors against Botulinum neurotoxin A protease through structure-activity relationship studies of chicoric acid
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Botulinum neurotoxins (BoNT) are among the most toxic known substances and currently there are no effective treatments for intraneuronal BoNT intoxication. Chicoric acid (ChA) was previously reported as a BoNT/A inhibitor that binds to the enzyme's α-exosite. Herein, we report the synthesis and structure-activity relationships (SARs) of a series of ChA derivatives, which revealed essential binding interactions between ChA and BoNT/A. Moreover, several ChA-based inhibitors with improved potency against the BoNT/A were discovered.
- Xue, Song,Seki, Hajime,Remes, Marek,?ilhár, Peter,Janda, Kim
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supporting information
p. 4956 - 4959
(2017/10/23)
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- Synthesis of novel 1,2,5-oxadiazoles and evaluation of action against Acinetobacter baumannii
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With multidrug resistant bacteria on the rise, novel antibiotics are becoming highly sought after. In 2008, eleven compounds were identified by high throughput screening as inhibitors of BasE, a key enzyme of the non-ribosomal peptide synthetase pathway found in Acinetobacter baumannii. Herein, we describe the preparation of four structurally similar heterocyclic lead compounds from that study, including one 1,2,5-oxadiazole. A further library of 30 analogues containing the oxadiazole moiety was then generated. All compounds were screened against Acinetobacter baumannii and their minimum inhibitory concentration data is reported, with (E)-3-(2-hydroxyphenyl)-N-(4-methyl-1,2,5-oxadiazol-3-yl)acrylamide 32 found to have an MIC of 0.5 mM. This work provides the foundation for further investigation of 1,2,5-oxadizoles as novel inhibitors of A. baumannii.
- Christoff, Rebecca M.,Murray, Gerald L.,Kostoulias, Xenia P.,Peleg, Anton Y.,Abbott, Belinda M.
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supporting information
p. 6267 - 6272
(2017/10/13)
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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 0138-0141
(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 0143; 0145
(2016/12/07)
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- Seven leaf lactone derivative and its preparation method and application
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The invention relates to an esculetin derivative, belonging to the field of specific curative activities of compounds or pharmaceutical preparation. The name of the derivative is 6,7-bi(5,6-diacetylcaffeoyl)-coumacetate, and the structural formula is as shown in the specification. The esculetin derivative disclosed by the invention is synthesized by taking natural medicinal monomers esculetin and caffeic acid as raw materials. The invention also provides a preparation method and application of the derivative. The derivative disclosed by the invention is a novel compound with good pharmaceutical activity, and the esculetin derivative prepared by the invention is subjected to raw material application in medicines for treating fever, inflammation and pain and has the effect of treating the fever, inflammation and pain.
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Paragraph 0039
(2017/02/02)
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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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- Discovery of novel hybrids of diaryl-1,2,4-triazoles and caffeic acid as dual inhibitors of cyclooxygenase-2 and 5-lipoxygenase for cancer therapy
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Inflammation plays a key role in cancer initiation and propagation. Cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX), two important enzymes in inflammatory responses are up-regulated in various tumor types. Dual inhibition of COX-2 and 5-LOX constitutes a rational concept for the design of more efficacious anti-tumor agents with an improved safety profile. We have previously reported a series of diaryl-1,2,4-triazole derivatives as selective COX-2 inhibitors. Herein, we hybridized the diaryl-1,2,4-triazoles with caffeic acid (CA) which was reported to display 5-LOX inhibitory and anti-tumor activities, affording a novel class of COX-2/5-LOX dual inhibitors as anti-tumor drug candidates. Most of these compounds exhibited potent COX-2/5-LOX inhibitory and antiproliferative activities in vitro. And the most potent compound 22b could significantly inhibit tumor growth in vivo. Furthermore, mechanistic investigation showed that the representative compound 15c blocked cell cycle in G2 phase and induced apoptosis in human non-small cell lung cancer A549 cells in a dose-dependent manner. Our preliminary investigation results would provide new clues for the cancer theatment with COX-2/5-LOX dual inhibitors.
- Cai, Hao,Huang, Xiaojing,Xu, Shengtao,Shen, Hao,Zhang, Pengfei,Huang, Yue,Jiang, Jieyun,Sun, Yijun,Jiang, Bo,Wu, Xiaoming,Yao, Hequan,Xu, Jingyi
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supporting information
p. 89 - 103
(2015/12/04)
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- ARYLOYL(OXY OR AMINO)PENTAFLUOROSULFANYLBENZENE COMPOUND, PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, AND PRODRUGS THEREOF
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An aryloyl(oxy or amino)pentafluorosulfanylbenzene compound having pharmacological action. The aryloyl(oxy or amino)pentafluorosulfanylbenzene compound is represented by general formula (A-I), a pharmaceutically acceptable salt thereof, and a prodrug ther
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Paragraph 0288-0290
(2016/09/26)
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- METHOD FOR MANUFACTURING 3,4,5-TRICAFFEOYLQUINIC ACID
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Provided are a method for manufacturing 3,4,5-tricaffeoylquinic acid, which can produce 3,4,5-tricaffeoylquinic acid with high efficiency by a simple operation in a short process using inexpensive raw materials, and intermediate compounds. The method for manufacturing 3,4,5-tricaffeoylquinic acid of the invention includes at least Step (1) of allowing a compound represented by Formula (1) or a compound represented by Formula (2) to react with a compound represented by Formula (4); and Step (2) of deprotecting the product obtained in Step (1), and producing 3,4,5-tricaffeoylquinic acid:
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Paragraph 0383; 0385
(2016/02/19)
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- Design, synthesis and evaluation of semi-synthetic triazole-containing caffeic acid analogues as 5-lipoxygenase inhibitors
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In this work the synthesis, structure-activity relationship (SAR) and biological evaluation of a novel series of triazole-containing 5-lipoxygenase (5-LO) inhibitors are described. The use of structure-guided drug design techniques provided compounds that
- De Lucia, Daniela,Lucio, Oscar Méndez,Musio, Biagia,Bender, Andreas,Listing, Monika,Dennhardt, Sophie,Koeberle, Andreas,Garscha, Ulrike,Rizzo, Roberta,Manfredini, Stefano,Werz, Oliver,Ley, Steven V.
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supporting information
p. 573 - 583
(2015/07/28)
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- Novel 9H-carbazole ester derivative, the preparation thereof and composition containing the same for preventing or treating vascular disease
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The present invention relates to a novel 9H-carbazole ester derivative, a method for preparing the same, and a composition containing the same for preventing or treating vascular disease. The novel 9H-carbazole ester derivative has very excellent platelet
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Paragraph 0427-0428; 0430
(2021/05/16)
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- Antiproliferative, antiandrogenic and cytotoxic effects of novel caffeic acid derivatives in LNCaP human androgen-dependent prostate cancer cells
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Caffeic acid and its naturally occurring derivative caffeic acid phenethyl ester (CAPE) have antiproliferative and cytotoxic properties in a variety of cancer cell lines without displaying significant toxicity toward healthy cells, and are considered to be potential anticancer agents. However, little is known about their effects on prostate cancer cells. We synthesized and evaluated the effects of caffeic acid, CAPE (2) and 18 synthetic derivatives on cell viability and androgen-dependent cell proliferation, subcellular localisation and expression of androgen receptor (AR) and secretion of prostate-specific antigen (PSA) in LNCaP human hormone-dependent prostate cancer cells. Several synthetic derivatives of CAPE were strong, concentration-dependent cytotoxic agents in LNCaP cells with IC50 values in the 6.8-26.6 μM range, potencies that were up to five-fold greater than that of CAPE (33.7 ± 4.0 μM). A number of caffeic acid derivatives were inhibitors of androgen-stimulated LNCaP cell proliferation with concomitant inhibition of DHT-stimulated PSA secretion. Compound 24 was the most cytotoxic and antiproliferative caffeic acid derivative (IC50 values of 6.8 ± 0.3 and 2.4 ± 0.8 μM, respectively) inhibiting DHT-stimulated cell proliferation and PSA secretion statistically significantly at concentrations as low as 0.3 μM. Exposure to DHT increased cytoplasmic and nuclear AR levels and co-treatment with increasing concentrations of compound 24 or CAPE (2), notably, further increased these levels. In conclusion, a number of synthetic derivatives of caffeic acid are potent inhibitors of androgen-dependent prostate cancer cell proliferation and viability, acting, at least in part, via an antiandrogenic mechanism that involves increased nuclear accumulation of (presumably inactive) AR.
- Sanderson, J. Thomas,Clabault, Hélène,Patton, Cody,Lassalle-Claux, Grégoire,Jean-Fran?ois, Jacques,Paré, Aurélie F.,Hébert, Martin J.G.,Surette, Marc E.,Touaibia, Mohamed
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p. 7182 - 7193
(2013/11/06)
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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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- Performances of CN-columns for the analysis of γ-oryzanol and its p-coumarate and caffeate derivatives by normal phase HPLC and a validated method of quantitation
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γ-Oryzanol is an important phytochemical used in pharmaceutical, alimentary and cosmetic preparations. The present article, for the first time, discloses the performances of NP-HPLC in separating γ-oryzanol components and develops a validated method for i
- D'Ambrosio, Michele
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p. 2079 - 2088
(2013/06/26)
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- Caffeic acid derivatives: A new type of influenza neuraminidase inhibitors
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Recently, many natural products, especially some plant-derived polyphenols have been found to exert antiviral effects against influenza virus and show inhibitory activities on neuraminidases (NAs). In our research, we took caffeic acid which contained two phenolic hydroxyl groups as the basic fragment to build a small compound library with various structures. The enzyme inhibition result indicated that some compounds exhibited moderate activities against NA and compound 15d was the best with IC50 = 7.2 μM and 8.5 μM against N2 and N1 NAs, respectively. The 3,4-dihydroxyphenyl group from caffeic acid was important for the activity according to the docking analysis. Besides, compound 15d was found to be a non-competitive inhibitor with Ki = 11.5 ± 0.25 μM by the kinetic study and also presented anti-influenza virus activity in chicken embryo fibroblast cells. It seemed promising to discover more potent NA inhibitors from caffeic acid derivatives to cope with influenza virus.
- Xie, Yuanchao,Huang, Bing,Yu, Kexiang,Shi, Fangyuan,Liu, Tianqi,Xu, Wenfang
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supporting information
p. 3556 - 3560
(2013/07/04)
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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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- Further discovery of caffeic acid derivatives as novel influenza neuraminidase inhibitors
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Eight series of compounds, each series containing two to five compounds were prepared by structural modifications of a lead, which was previously discovered as a mild influenza neuraminidase (NA) inhibitor. On the basis of the biological result, a detailed structure-activity relationship (SAR) was derived and discussed. Several caffeic acid derivatives that acted as non-competitive inhibitors were close or superior to the lead and also presented good antiviral activities in cells. Besides, it was interesting to find that modifications of the lead with different strategies could result in selective inhibition against N1 or N2. The preliminary docking analysis indicated that the 150-cavity of the enzymes played an important role in the selective inhibition.
- Xie, Yuanchao,Huang, Bing,Yu, Kexiang,Xu, Wenfang
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p. 7715 - 7723
(2014/01/06)
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- Synthesis and HIV-1 inhibitory activities of dicaffeoyl and digalloyl esters of quinic acid derivatives
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Twenty analogues of the anti-HIV-1 integrase (IN) inhibitors dicaffeoylquinic acids (DCQAs) were prepared. Their IC50 values for 3'-end processing and strand transfer against recombinant HIV-1IN were determined in vitro, and their cell toxiciti
- Junior,Verde,Rezende,Caneschi,Couri,McDougall,Robinson Jr.,De Almeida
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p. 724 - 733
(2013/07/28)
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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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- A stereocomplex of poly(lactide)s with chain end modification: Simultaneous resistances to melting and thermal decomposition
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The simultaneous improvement of the melting temperature (Tm = 224 °C) and the decomposition temperature (T10 = 359 °C) of poly(lactide)s was achieved by the stereocomplex formation of poly(l-lactide) and poly(d-lactide) with bio-based aromatic groups at both initiating and terminating chain ends.
- Ajiro, Hiroharu,Hsiao, Yi-Ju,Thi, Tran Hang,Fujiwara, Tomoko,Akashi, Mitsuru
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experimental part
p. 8478 - 8480
(2012/09/21)
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- Nitrogen-containing polyhydroxylated aromatics as HIV-1 integrase inhibitors: Synthesis, structure-activity relationship analysis, and biological activity
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Four series of forty-five nitrogen-containing polyhydroxylated aromatics based on caffeic acid phenethyl ester were designed and synthesized as HIV-1 integrase (IN) inhibitors. Most of these compounds inhibited IN catalytic activities in low micromolar range. Among these new analogues, compounds 9e and 9f were the most potent IN inhibitors with IC50 value of 0.7 μM against strand transfer reaction. Their key structure-activity relationships were also discussed.
- Yu, Shenghui,Zhang, Linna,Yan, Shifeng,Wang, Peng,Sanchez, Tino,Christ, Frauke,Debyser, Zeger,Neamati, Nouri,Zhao, Guisen
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p. 628 - 640
(2012/10/29)
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- Structure-activity relationship of caffeoylquinic acids on the accelerating activity on ATP production
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Caffeoylquinic acid (CQA) is one of the phenylpropanoids which have various bioactivities such as antioxidant, antibacterial, anticancer, antihistamic, and other biological effects. We previously reported that 3,5-di-O-caffeoylquinic acid inhibited amyloid β1-42-induced cellular toxicity on human neuroblastoma SH-SY5Y cells and increased the mRNA expression level of glycolytic enzymes and the intracellular ATP level. To investigate structure-activity relationship on the accelerating activity on ATP production, we synthesized 1,4,5-tri-O-caffeoylquinic acid, 4,5-di-O-caffeoylquinic acid, 3,4,5-tri-O-caffeoylquinic acid, and other derivatives. Additionally, we evaluated intracellular ATP level in SH-SY5Y treated with each CQA derivative. As a result, 3,4,5-tri-O-caffeoylquinic acid showed the highest accelerating activity on ATP production among tested compounds. It was suggested that caffeoyl groups bound to quinic acid are important for activity and the more caffeoyl groups are bound to quinic acid, the higher accelerating activity on ATP production exhibits.
- Miyamae, Yusaku,Kurisu, Manami,Han, Junkyu,Isoda, Hiroko,Shigemori, Hideyuki
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body text
p. 502 - 507
(2011/06/10)
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- Mechanism of high thermal stability of commercial polyesters and polyethers conjugated with bio-based caffeic acid
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In previous report, we discovered that a novel improvement technique to enhance the thermal properties of poly(L-lactide)s (PLLAs) by terminal conjugation with 3,4-diacetoxycinnamic acid (DACA). In this study, we clarified the mechanism of the enhancement of thermal stability by using commercial polyesters and polyethers. The effect of thermal improvement by the terminal conjugation of DACA on poly(DL-lactide), poly(ε-caprolactone), and poly(ethylene glycol) was almost the same as about 100 °C increase. The amount of residual tin catalyst, which enhances the thermal degradation of polyesters, was reduced at undetected level after the terminal conjugation of DACA probably due to the removal of tin during DACA conjugation process. Furthermore, the π-π stacking interactions of DACA units and the chemical protection of terminal hydroxyl groups, which enhances intramolecular scission, were also important for the high thermal stability. We clarified that the extreme high thermal stability by DACA conjugation was induced by these above mechanisms.
- Thi, Tran Hang,Matsusaki, Michiya,Hirano, Hiroshi,Kawano, Hiroaki,Agari, Yasuyuki,Akashi, Mitsuru
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experimental part
p. 3152 - 3162
(2012/05/19)
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- Redox-silent tocotrienol esters as breast cancer proliferation and migration inhibitors
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Tocotrienols are vitamin E members with potent antiproliferative activity against preneoplastic and neoplastic mammary epithelial cells with little or no effect on normal cell growth or functions. However, physicochemical and pharmacokinetic properties gr
- Behery, Fathy A.,Elnagar, Ahmed Y.,Akl, Mohamed R.,Wali, Vikram B.,Abuasal, Bilal,Kaddoumi, Amal,Sylvester, Paul W.,El Sayed, Khalid A.
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experimental part
p. 8066 - 8075
(2011/02/21)
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- TOLL LIKE RECEPTOR (TLR) SIGNALING ANTAGONIST
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The present invention relates to novel synthetic toll like receptor antagonist. The present invention in particular provides compounds, methods and compositions for specifically inhibiting immune stimulation involving TLR ligands, especially TLR-4. The compounds are potentially useful in treatment of inflammation, autoimmunity, allergy, asthma, graft rejection, graft versus host disease, infection, sepsis, cancer and immunodeficiency.
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Page/Page column 12
(2009/09/07)
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- Design and synthesis of novel nitrogen-containing polyhydroxylated aromatics as HIV-1 integrase inhibitors from caffeic acid phenethyl ester
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A series of nitrogen-containing polyhydroxylated aromatics from caffeic acid phenethyl ester were designed and synthesized as HIV-1 integrase inhibitors. Most of these compounds exhibited potent inhibitory activities at micromolar concentrations against HIV-1 integrase in the 3′-end processing and the strand transfer. Their key structure-activity relationship was also discussed.
- Wang, Peng,Liu, Chuan,Sanches, Tino,Zhong, Yuan,Liu, Bo,Xiong, Junlong,Neamati, Nouri,Zhao, Guisen
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supporting information; experimental part
p. 4574 - 4578
(2010/04/24)
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- A simple approach to pyrazol-3-ones via diazenes
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An efficient entry into pyrazol-3-ones is described starting from propenoic acids that were first transformed into the corresponding hydrazides. Oxidation of the hydrazides gave the diazenes and the latter cyclized to pyrazol-3-ones on treatment with ZrCl4. The methoxycarbonyl protection of the N-1 of the pyrazolone derivatives was easily removed under mild reaction conditions.
- Burja, Bojan,Ko?evar, Marijan,Polanc, Slovenko
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experimental part
p. 8690 - 8696
(2009/12/26)
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- Thermally stable and photoreactive polylactides by the terminal conjugation of bio-based caffeic acid
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Caffeic acid terminally conjugated with polylactide showed high thermal stability and photoreactivity, and may be useful as a functional polylactide in the environmental and medical fields. The Royal Society of Chemistry.
- Hang Thi, Tran,Matsusaki, Michiya,Akashi, Mitsuru
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supporting information; body text
p. 3918 - 3920
(2009/02/08)
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- Induction of adiponectin by natural and synthetic phenolamides in mouse and human preadipocytes and its enhancement by docosahexaenoic acid
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Adiponectin, the adipose-derived cytokine, plays an important role in preventing metabolic syndromes. To develop new adiponectin inducers, eight species of ferulic esters and amides, and five related compounds were synthesized and tested on the stimulation of adiponectin production in mouse 3T3-L1 and normal human preadipocytes. The ferulamides with an aromatic ring in the N-substituent are very active in inducing adiponectin as compared with the known active compounds, curcumin, [6]-gingerol, and capsaicin, and furthermore the activities of these ferulamides are remarkably stronger than those of the corresponding esters or the straight chain octylamide. The most active compound, N-(2-phenylethyl)ferulamide (7), was found to activate the PPAR (peroxisome proliferator-activated receptor) γ-RXR (retinoid X receptor) α heterodimeric complex in the PPRE (PPAR-responsive element)-driven luciferase reporter assay. The adiponectin production by 7 is synergistically enhanced by coaddition of a PPARγ-specific agonist, pioglitazone (PGZ), or another PPARγ agonist, docosahexaenoic acid (DHA), in cultured preadipocytes. The compound 7 alone did not show a statistically significant effect on the plasma adiponectin level in KK-Ay/Ta mice, while 1% 7 in the diets significantly lowered the blood glucose and triglyceride levels and 0.3% 7 mixed with DHA oil in the diets significantly increased the adiponectin level as compared with the control. These results suggest that the present ferulamides would be useful lead compounds in developing more potent agents for treatment of metabolic syndromes through promoting the endogenous adiponectin production, and that such an activity is possibly enhanced by the coadministration with DHA.
- Yamazaki, Yoshimitsu,Kawano, Yasuhiro,Uebayasi, Masami
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p. 290 - 300
(2008/09/16)
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- Antimycobacterial activity of cinnamate-based esters of the triterpenes betulinic, oleanolic and ursolic acids
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Betulinic acid, oleanolic acid and ursolic acid have been modified at the C-3 position to cinnamate-based esters and in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Ra has been determined. The results indicated that mo
- Tanachatchairatana, Tanud,Bremner, John Barnard,Chokchaisiri, Ratchanaporn,Suksamrarn, Apichart
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p. 194 - 198
(2008/09/18)
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- Synthetic pentacyclic triterpenoids and derivatives of betulinic acid and betulin
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The present invention comprises small molecule inhibitors of cell proliferative conditions, in particular cancer and conditions associated with cancer. For example, associated malignancies include ovarian cancer, cervical cancer, breast cancer, colorectal cancer, and glioblastomas, among others. Accordingly, the compounds of the present invention are useful for treating, preventing, and/or inhibiting these diseases. Thus, the present invention also comprising pharmaceutical formulations comprising the compounds and methods of using the compounds and formulations to inhibit cancer and treat, prevent, or inhibit the foregoing diseases.
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Page/Page column 49
(2010/11/28)
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- Quantitative analysis of N-phenylpropenoyl-L-amino acids in roasted coffee and cocoa powder by means of a stable isotope dilution assay
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Since recent reports on the role of N-phenylpropenoyl-L-amino acids as powerful antioxidants and key contributors to the astringent taste of cocoa nibs, there is an increasing interest in the concentrations of these phytochemicals in plant-derived foods.
- Stark, Timo,Justus, Helene,Hofmann, Thomas
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p. 2859 - 2867
(2007/10/03)
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