103188-47-2Relevant articles and documents
Synthesis and evaluation of multifunctional ferulic and caffeic acid dimers for Alzheimer’s disease
He, Xi-Xin,Yang, Xiao-Hong,Ou, Rui-Ying,Ouyang, Ying,Wang, Sheng-Nan,Chen, Zi-Wei,Wen, Shi-Jun,Pi, Rong-Biao
, p. 734 - 737 (2017)
In this study, a series of novel ferulic and caffeic acid dimers was designed and synthesised, and their multifunctional properties against Alzheimer’s disease (AD) were evaluated. Results showed that our multifunctional strategy was great supported by en
Free radical scavenging and antioxidative activity of caffeic acid amide and ester analogues: Structure-activity relationship
Son, Sopheak,Lewis, Betty A.
, p. 468 - 472 (2002)
The structure-activity relationships of synthetic caffeic acid amide and ester analogues as potential antioxidants and free radical scavengers have been investigated. The 2,2-diphenyl-1-picrylhydrazyl radical (DPPH·) scavenging activity of the test compounds was N-trans-caffeoyl-L-cysteine methyl ester (5) > N-trans-caffeoyldopamine (4) > N-trans-caffeoyltyramine (3) > N-trans-caffeoyl-β-phenethylamine (2) > Trolox C (8) > caffeic acid phenethyl ester (1) > caffeic acid (6) > ferulic acid (7). This established that the radical scavenging activity of the compounds increased with increasing numbers of hydroxyl groups or catechol moieties and also with the presence of other hydrogen-donating groups (-NH, -SH). The antioxidative activity of the compounds was also investigated in an emulsified linoleic acid oxidation system accelerated by 2,2′-azobis(2-amidinopropane) dihydrochloride. The order was 1 > 2 > 4 > 3 ≥ 5 > 6 > 8 > 7. Therefore, in the emulsion system, the antioxidative activity of the test compounds depends not only on the hydroxyl groups or catechol rings but also on the partition coefficient (log P) or hydrophobicity of the compounds. This supports the concept that hydrophobic antioxidants tend to exhibit better antioxidative activity in an emulsion system.
Catechol-based inhibitors of bacterial urease
Pagoni, Aikaterini,Daliani, Theohari,Macegoniuk, Katarzyna,Vassiliou, Stamatia,Berlicki, ?ukasz
supporting information, p. 1085 - 1089 (2019/03/07)
Targeted covalent inhibitors of urease were developed on the basis of the catechol structure. Forty amide and ester derivatives of 3,4-dihydroxyphenylacetic acid, caffeic acid, ferulic acid and gallic acid were obtained and screened against Sporosarcinia pasteurii urease. The most active compound, namely propargyl ester of 3,4-dihydroxyphenylacetic acid exhibited IC50 = 518 nM andkinact/Ki = 1379 M?1 s?1. Inhibitory activity of this compound was better and toxicity lower than those obtained for the starting compound – catechol. The molecular modelling studies revealed a mode of binding consistent with structure-activity relationships.
Design, synthesis, and evaluation of caffeic acid amides as synergists to sensitize fluconazole-resistant Candida albicans to fluconazole
Dai, Li,Zang, Chengxu,Tian, Shujuan,Liu, Wei,Tan, Shanlun,Cai, Zhan,Ni, Tingjunhong,An, Maomao,Li, Ran,Gao, Yue,Zhang, Dazhi,Jiang, Yuanying
, p. 34 - 37 (2015/02/19)
A series of caffeic acid amides were designed, synthesized, and their synergistic activity with fluconazole against fluconazole-resistant Candida albicans was evaluated in vitro. The title caffeic acid amides 3-30 except 26 exhibited potent activity, and the subsequent SAR study was conducted. Compound 3, 5, 21, and 34c, at a concentration of 1.0 μg/ml, decreased the MIC80 of fluconazole from 128.0 μg/ml to 1.0-0.5 μg/ml against the fluconazole-resistant C. albicans. This result suggests that the caffeic acid amides, as synergists, can sensitize drug-resistant fungi to fluconazole. The SAR study indicated that the dihydroxyl groups and the amido groups linking to phenyl or heterocyclic rings are the important pharmacophores of the caffeic acid amides.
