Antineoplastic agents. 465. Structural modification of resveratrol: sodium resverastatin phosphate.

Abstract

As an extension of structure/activity investigations of resveratrol (1), phenstatin (2c), and the cancer antiangiogenesis drug sodium combretastatin A-4 phosphate (2b), syntheses of certain related stilbenes (14) and benzophenones (16) were undertaken. The trimethyl ether derivative of (Z)-resveratrol (4a) exhibited the strongest activity (GI(50) = 0.01-0.001 microg/mL) against a minipanel of human cancer cell lines. A monodemethylated derivative (14c) was converted to prodrug 14n (sodium resverastatin phosphate) for further biological evaluation. The antitubulin and antimicrobial activities of selected compounds were also evaluated.

• Authors: George R Pettit, Matthew P Grealish, M Katherine Jung, Ernest Hamel, Robin K Pettit, J-Charles Chapuis, Jean M Schmidt
• Journal: Journal of medicinal chemistry (J Med Chem) Vol. 45 Issue 12 Pg. 2534-42 (Jun 06 2002) ISSN: 0022-2623 [Print] United States
• PMID: 12036362 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't, Research Support, U.S. Gov't, P.H.S.)

Chemical References

• Anti-Bacterial Agents
• Anti-Infective Agents
• Antineoplastic Agents
• Biopolymers
• Organophosphates
• Prodrugs
• Stilbenes
• Tubulin
• resverstatin phosphate
• Resveratrol

Topics

• Anti-Bacterial Agents
• Anti-Infective Agents (chemical synthesis, chemistry, pharmacology)
• Antineoplastic Agents (chemical synthesis, chemistry, pharmacology)
• Bacteria (drug effects)
• Biopolymers
• Cell Division (drug effects)
• Drug Screening Assays, Antitumor
• Fungi (drug effects)
• Humans
• Microbial Sensitivity Tests
• Organophosphates (chemical synthesis, chemistry, pharmacology)
• Prodrugs (chemical synthesis, chemistry, pharmacology)
• Resveratrol
• Stereoisomerism
• Stilbenes (chemical synthesis, chemistry, pharmacology)
• Structure-Activity Relationship
• Tubulin (chemistry)
• Tumor Cells, Cultured