22020-28-6Relevant articles and documents
Structure?Activity Relationships of Cinnamate Ester Analogues as Potent Antiprotozoal Agents
Bernal, Freddy A.,Kaiser, Marcel,Wünsch, Bernhard,Schmidt, Thomas J.
, p. 68 - 78 (2019/11/22)
Protozoal infections are still a global health problem, threatening the lives of millions of people around the world, mainly in impoverished tropical and sub-tropical regions. Thus, in view of the lack of efficient therapies and increasing resistances against existing drugs, this study describes the antiprotozoal potential of synthetic cinnamate ester analogues and their structure-activity relationships. In general, Leishmania donovani and Trypanosoma brucei were quite susceptible to the compounds in a structure-dependent manner. Detailed analysis revealed a key role of the substitution pattern on the aromatic ring and a marked effect of the side chain on the activity against these two parasites. The high antileishmanial potency and remarkable selectivity of the nitro-aromatic derivatives suggested them as promising candidates for further studies. On the other hand, the high in vitro potency of catechol-type compounds against T. brucei could not be extrapolated to an in vivo mouse model.
Synthesis, Antibacterial Evaluation, and QSAR of Caffeic Acid Derivatives
Araújo, Marianna O.,Freire Pessoa, Hilzeth L.,Lira, Andressa B.,Castillo, Yunierkis P.,De Sousa, Dami?o P.
, (2019/03/07)
The present study evaluates the antibacterial effects of a set of 16 synthesized caffeic acid ester derivatives against strains of Staphylococcus aureus and Escherichia coli, as well as discusses their structure-activity relationship (SAR). The antibacterial assays were performed using microdilution techniques in 96-well microplates to determine minimal inhibitory concentration (MIC). The results revealed that five of the compounds present strong to optimum antibacterial effect. Of the sixteen ester derivatives evaluated, the products with alkyl side chains, as propyl caffeate (3), butyl caffeate (6), and pentyl caffeate (7), presented the best antibacterial activity with MIC values of around 0.20 μM against Escherichia coli and only butyl caffeate (6) showing the same MIC against Staphylococcus aureus. For products with aryl substituents, the best MIC results against the tested strain of Escherichia coli were 0.23 μM for (di-(4-chlorobenzyl)) caffeate (13) and 0.29 μM for diphenylmethyl caffeate (10) and all were less active against the Staphylococcus aureus strain. Preliminary quantitative structure-activity relationship (QSAR) analyses confirmed that certain structural characteristics, such as a median linear carbon chain and the presence of electron withdrawal substituents at the para position of the aromatic ring, help potentiate antibacterial activity.
Enzymatic Synthesis and Antioxidant Activity of 1-Caffeoylglycerol Prepared from Alkyl Caffeates and Glycerol
Meng, Xiang-Yun,Xu, Yan,Wu, Jin-Xian,Zhu, Chang-Tong,Zhang, Dong-Yang,Wu, Guo-Hua,Wu, Fu-An,Wang, Jun
, p. 149 - 159 (2018/03/21)
Caffeic acid (CA) as a strong antioxidant has lower solubility in nonpolar media, which limits its application in the food industry. To increase the lipophilicity of CA, 1-caffeoylglycerol (1-CG) was synthesized by lipase-catalyzed transesterification of
