Next Article in Journal
Synthesis and Evaluation of a Series of Novel Asymmetrical Curcumin Analogs for the Treatment of Inflammation
Previous Article in Journal
A Novel Phage-Library-Selected Peptide Inhibits Human TNF-α Binding to Its Receptors
Article Menu

Export Article

Open AccessArticle
Molecules 2014, 19(6), 7269-7286; doi:10.3390/molecules19067269

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

State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210093, China
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Received: 4 May 2014 / Revised: 26 May 2014 / Accepted: 27 May 2014 / Published: 3 June 2014
(This article belongs to the Section Medicinal Chemistry)
View Full-Text   |   Download PDF [757 KB, uploaded 18 June 2014]   |  

Abstract

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. View Full-Text
Keywords: caffeic acid derivates; EGFR; cell migration inhibition; antitumor activity; structure-activity relationship caffeic acid derivates; EGFR; cell migration inhibition; antitumor activity; structure-activity relationship
Figures

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Supplementary material

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Yuan, J.-W.; Qiu, H.-Y.; Wang, P.-F.; Makawana, J.A.; Yang, Y.-A.; Zhang, F.; Yin, Y.; Lin, J.; Wang, Z.-C.; Zhu, H.-L. 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 2014, 19, 7269-7286.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top