E-Combretastatin and E-resveratrol structural modifications: antimicrobial and cancer cell growth inhibitory beta-E-nitrostyrenes

  • Bioorg Med Chem. 2009 Sep 15;17(18):6606-12. doi: 10.1016/j.bmc.2009.07.076.
Robin K Pettit  1 ,  George R Pettit ,  Ernest Hamel ,  Fiona Hogan ,  Bryan R Moser ,  Sonja Wolf ,  Sandy Pon ,  Jean-Charles Chapuis ,  Jean M Schmidt
Affiliations
  • 1. Cancer Research Institute and Department of Chemistry and Biochemistry, Arizona State University, PO Box 871604, Tempe, AZ 85287-1604, United States. [email protected]
PMID: 19709889 DOI: 10.1016/j.bmc.2009.07.076
Abstract

As part of a broad-based SAR investigation of E-resveratrol (strong Sirtuin Activator and antineoplastic) and the Anticancer vascular-targeting combretastatin-type Stilbenes, a series of twenty-three beta-E-nitrostyrenes was synthesized in order to evaluate potential antineoplastic, antitubulin, and antimicrobial activities. The beta-E-nitrostyrenes evaluated ranged from monosubstituted Phenols to trimethoxy and 3-methoxy-4,5-methylenedioxy derivatives. Two of the beta-nitrostyrenes were synthesized as water-soluble sodium phosphate derivatives (4t, 4v). All except four (4r, 4s, 4t, 4u) of the series significantly inhibited a minipanel of human Cancer cell lines. All but eight led to an IC(50) of <10 microM for inhibition of tubulin polymerization, and all except three (4l, 4t, 4v) displayed antimicrobial activity.

Products