98631-72-2Relevant academic research and scientific papers
Development trans-N-benzyl hydroxyl cinnamamide based compounds from cinnamic acids and characteristics anticancer potency
Agustan, Agustan,Bahriah, Bahriah,Dali, Seniwati,Firdausiah, Syadza,Rasyid, Herlina,Soekamto, Nunuk Hariani,Tahir, Dahlang,Zenta, Firdaus
, (2022/01/31)
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
Novel 3C-like protease inhibitor as well as preparation method and application thereof
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Paragraph 0047-0048; 0057-0059, (2021/09/26)
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.
Design, synthesis of Cinnamyl-paeonol derivatives with 1, 3-Dioxypropyl as link arm and screening of tyrosinase inhibition activity in vitro
Tang, Kai,Jiang, Yi,Zhang, Huawei,Huang, Wenli,Xie, Yundong,Deng, Chong,Xu, Hongbo,Song, Xiaomei,Xu, Hong
, (2020/12/13)
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
Synthesis of caffeic acid sulfonamide derivatives and their protective effect against H2O2 induced oxidative damage in A549 cells
Chen, Hailan,Hu, Tingjun,Lin, Cuiwu,Natarajan, Bharathi,Peng, Xiaoyu,Wei, Jiata,Yan, Hao,Zhang, Yuxue,Zhao, Anran
, p. 9924 - 9933 (2020/03/23)
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.
Cinnamate derivatives and application of cinnamate derivatives as tyrosinase inhibitors and gels
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Paragraph 0077-0079; 0081; 0091-0094, (2020/08/02)
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.
Synthesis of novel caffeic acid derivatives and their protective effect against hydrogen peroxide induced oxidative stress via Nrf2 pathway
Chai, Ling,Chen, Hailan,Huang, Kelin,Lin, Cuiwu,Natarajan, Bharathi,Peng, Xiaoyu,Wu, Gang,Yang, Songxin,Zhao, Anran
, (2020/02/27)
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
Preparation method and application of hydroxyl cinnamyl ester type catechin
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Paragraph 0065; 0071; 0089, (2020/06/24)
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.
Sevanol and its analogues: Chemical synthesis, biological effects and molecular docking
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.
, p. 1 - 21 (2020/07/31)
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
N-Cinnamoylanthranilates as human TRPA1 modulators: Structure-activity relationships and channel binding sites
Chandrabalan, Arundhasa,McPhillie, Martin J.,Morice, Alyn H.,Boa, Andrew N.,Sadofsky, Laura R.
supporting information, p. 141 - 156 (2019/03/17)
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.
Caffeic acid esters are effective bactericidal compounds against paenibacillus larvae by altering intracellular oxidant and antioxidant levels
Collins, William,Lowen, Noah,Blake, David J.
, (2019/08/13)
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.
