Synthesis of Caffeic Acid Amides Bearing 2,3,4,5-Tetra-hydrobenzo[b][1,4]dioxocine Moieties and Their Biological Evaluation as Antitumor Agents

Molecules

Ji-Wen Yuan¹  Han-Yue Qiu¹  Peng-Fei Wang²  Jigar A. Makawana²  Yong-An Yang²  Fei Zhang²  Yong Yin²  Jie Lin²  Zhong-Chang Wang² 

[1] id="af1-molecules-19-07269">State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210093, Chi

关键词: caffeic acid derivates;    EGFR;    cell migration inhibition;    antitumor activity;    structure-activity relationship;   

DOI  :  10.3390/molecules19067269

来源: mdpi

【 摘 要 】

A series of caffeic acid amides D₁-D₁₇ bearing 2,3,4,5-tetrahydrobenzo-[b][1,4]dioxocine units has been synthesized and their biological activities evaluated for potential antiproliferative and EGFR inhibitory activity. Of all the compounds studied, compound D₉ showed the most potent inhibitory activity (IC₅₀ = 0.79 μM for HepG2 and IC₅₀ = 0.36 μM for EGFR). The structures of compounds were confirmed by ¹H-NMR, ESI-MS and elemental analysis. Among all, the structure of compound D₉ ((E)-N-(4-ethoxyphenyl)-3-(2,3,4,5-tetrahydrobenzo[b][1,4]dioxocin-8-yl)acrylamide) was also determined by single-crystal X-ray diffraction analysis. Compound D₉ was found to be a potential antitumor agent according to biological activity, molecular docking, apoptosis assay and inhibition of HepG2.

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.