Antineoplastic agents. 579. Synthesis and cancer cell growth evaluation of E-stilstatin 3

A resveratrol structural modification

George Pettit, Noeleen Melody, Andrew Thornhill, John C. Knight, Thomas L. Groy, Cherry L. Herald

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

As an extension of our earlier structure/activity investigation of resveratrol (1a) cancer cell growth inhibitory activity compared to the structurally related stilbene combretastatin series (e.g., 2a), an efficient synthesis of E-stilstatin 3 (3a) and its phosphate prodrug 3b was completed. The trans-stilbene 3a was obtained using a convergent synthesis employing a Wittig reaction with phosphonium bromide 9 as the key reaction step. Deprotection of the Z-silyl ether 13 gave E-stilstatin 3 (3a) as the exclusive product. The structure and stereochemistry of 3a was confirmed by X-ray crystal structure determination.

Original languageEnglish (US)
Pages (from-to)1637-1642
Number of pages6
JournalJournal of Natural Products
Volume72
Issue number9
DOIs
StatePublished - Sep 25 2009

Fingerprint

Stilbenes
Cell growth
Antineoplastic Agents
Stereochemistry
Prodrugs
Growth
Bromides
Ether
Neoplasms
Crystal structure
Phosphates
X-Rays
X rays
stilstatin 3
resveratrol
combretastatin

ASJC Scopus subject areas

  • Complementary and alternative medicine
  • Molecular Medicine
  • Organic Chemistry
  • Analytical Chemistry
  • Pharmaceutical Science
  • Pharmacology
  • Drug Discovery

Cite this

Antineoplastic agents. 579. Synthesis and cancer cell growth evaluation of E-stilstatin 3 : A resveratrol structural modification. / Pettit, George; Melody, Noeleen; Thornhill, Andrew; Knight, John C.; Groy, Thomas L.; Herald, Cherry L.

In: Journal of Natural Products, Vol. 72, No. 9, 25.09.2009, p. 1637-1642.

Research output: Contribution to journalArticle

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