Synthesis and antitumor activity of feruloyl and caffeoyl derivatives

• Published in: Bioorganic & medicinal chemistry letters 2014-09, Vol.24 (18), p.4367-4371
• Main Authors: Chen, Hui-zhen, Chen, You-bao, Lv, Ya-ping, Zeng, Fang, Zhang, Juan, Zhou, Yong-lie, Li, Han-bing, Chen, Li-fei, Zhou, Bin-jie, Gao, Jian-rong, Xia, Chun-nian
• Format: Article
• Language: English
• Subjects: Antineoplastic Agents, Phytogenic - chemical synthesis; Antineoplastic Agents, Phytogenic - chemistry; Antineoplastic Agents, Phytogenic - pharmacology; Antitumor; Apoptosis - drug effects; Caffeic Acids - chemical synthesis; Caffeic Acids - chemistry; Caffeic Acids - pharmacology; Caffeoyl; Cell Line, Tumor; Cell Proliferation - drug effects; Coumaric Acids - chemical synthesis; Coumaric Acids - chemistry; Coumaric Acids - pharmacology; Dose-Response Relationship, Drug; Drug Screening Assays, Antitumor; Feruloyl; HeLa Cells; Hep G2 Cells; HL-60 Cells; Humans; Molecular Structure; SARs; Structure-Activity Relationship
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2014.08.024

A series of feruloyl and caffeoyl derivatives from commercial vanillin and veratraldehyde were synthesized by two convenient methods. Most compounds demonstrated attractive cytotoxicity and several new compounds demonstrated significant antiproliferative and cytotoxic activities against HeLa and Bewo tumor cell lines. We developed two efficient protocols for the synthesis of feruloyl and caffeoyl derivatives from commercial vanillin and veratraldehyde. Pharmacological activities were assessed against a panel of human cancer cell lines in vitro. Most synthesized compounds demonstrated attractive cytotoxicity. Several new compounds demonstrated significant antiproliferative and cytotoxic activities against HeLa and Bewo tumor cell lines. In particular, 5-nitro caffeic adamantyl ester showed broad spectrum of tumor inhibition in 10 cell lines, and reduced tumor weight by 36.7% in vivo when administered at a dose of 40mgkg−1.