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Antineoplastic agents. 443. Synthesis of the cancer cell growth inhibitor hydroxyphenstatin and its sodium diphosphate prodrug.

Abstract：

:A structure-activity relationship (SAR) study of the South African willow tree (Combretum caffrum) antineoplastic constituent combretastatin A-4 (3b) led to the discovery of a potent cancer cell growth inhibitor designated phenstatin (5a). This benzophenone derivative of combretastatin A-4 showed remarkable antineoplastic activity, and the benzophenone derivative of combretastatin A-1 was therefore synthesized. The benzophenone, designated hydroxyphenstatin (6a), was synthesized by coupling of a protected bromobenzene and a benzaldehyde to give the benzhydrol with subsequent oxidation to the ketone. Hydroxyphenstatin was converted to the sodium phosphate prodrug (6e) by a dibenzyl phosphite phosphorylation and subsequent benzyl cleavage (6a --> 6d --> 6e). While hydroxyphenstatin (6a) was a potent inhibitor of tubulin polymerization with activity comparable to that of combretastatin A-1 (3a), the phosphorylated derivative (6e) was inactive.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Pettit GR,Grealish MP,Herald DL,Boyd MR,Hamel E,Pettit RK

doi

10.1021/jm000045a

keywords:

subject

Has Abstract

pub_date

2000-07-13 00:00:00

pages

2731-7

issue

14

eissn

0022-2623

issn

1520-4804

pii

jm000045a

journal_volume

43

pub_type

杂志文章

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