Synthesis of trans-caffeate analogues and their bioactivities against HIV-1 integrase and cancer cell lines.

Abstract

Forty caffeate analogues were synthesized via a convenient method starting from vanillin with moderate to good yields. The testing of biological activity of these compounds against HIV-1 integrase indicates that four compounds: bornyl caffeate, bornyl 2-nitrocaffeate, 5-nitrocaffeic acid and 5-nitrocaffeic acid phenethyl ester (5-nitroCAPE) possess a good HIV integrase inhibitory activity, IC(50) 19.9, 26.8, 25.0 and 13.5 microM , respectively. Twelve caffeate analogues were tested by MTT assay on growth of human hepatocellular carcinoma BEL-7404, human breast MCF-7 adenocarcinoma, human lung A549 adenocarcinoma and human gastric cancer BCG823 cell lines, respectively. And the best result is IC(50) 5.5 microM for CAPE against BEL-7404.

• Authors: Chun-nian Xia, Hai-bo Li, Feng Liu, Wei-xiao Hu
• Journal: Bioorganic & medicinal chemistry letters (Bioorg Med Chem Lett) Vol. 18 Issue 24 Pg. 6553-7 (Dec 15 2008) ISSN: 1464-3405 [Electronic] England
• PMID: 18952420 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Antineoplastic Agents
• Caffeic Acids
• HIV Integrase Inhibitors
• Biotin
• HIV Integrase
• p31 integrase protein, Human immunodeficiency virus 1

Topics

• Antineoplastic Agents (chemical synthesis, pharmacology)
• Binding Sites
• Biotin (chemistry)
• Caffeic Acids (chemistry)
• Cell Line, Tumor
• Chemistry, Pharmaceutical (methods)
• Drug Design
• Enzyme-Linked Immunosorbent Assay
• HIV Integrase (chemistry)
• HIV Integrase Inhibitors (chemical synthesis, pharmacology)
• Humans
• Inhibitory Concentration 50
• Models, Chemical
• Structure-Activity Relationship