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

Forty caffeate analogues synthesized by one-pot methods were evaluated for their bioactivities. Four caffeate analogues possessed good HIV-IN inhibitory activities and several compounds showed good antitumor activities. Forty caffeate analogues were synthesized via a convenient method starting from...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2008-12, Vol.18 (24), p.6553-6557
Main Authors: Xia, Chun-nian, Li, Hai-bo, liu, Feng, Hu, Wei-xiao
Format: Article
Language:English
Subjects:
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antineoplastic agents
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - pharmacology
Antitumor
Antiviral agents
Binding Sites
Biological and medical sciences
Biotin - chemistry
Caffeate analogues
Caffeic Acids - chemistry
Cell Line, Tumor
Chemistry, Pharmaceutical - methods
Drug Design
Enzyme-Linked Immunosorbent Assay
General aspects
HIV Integrase - chemistry
HIV Integrase Inhibitors - chemical synthesis
HIV Integrase Inhibitors - pharmacology
HIV-1 integrase
Human immunodeficiency virus 1
Humans
Inhibitory Concentration 50
Medical sciences
Models, Chemical
Pharmacology. Drug treatments
Structure-Activity Relationship
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Summary:Forty caffeate analogues synthesized by one-pot methods were evaluated for their bioactivities. Four caffeate analogues possessed good HIV-IN inhibitory activities and several compounds showed good antitumor activities. 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 μM, 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 μM for CAPE against BEL-7404.
ISSN:0960-894X
0968-0896
1464-3405
1464-3391
DOI:10.1016/j.bmcl.2008.10.046