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

doi:10.1021/np9002146

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 journal › Article › peer-review

24 Scopus citations

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 language	English (US)
Pages (from-to)	1637-1642
Number of pages	6
Journal	Journal of Natural Products
Volume	72
Issue number	9
DOIs	https://doi.org/10.1021/np9002146
State	Published - Sep 25 2009

ASJC Scopus subject areas

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

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10.1021/np9002146

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T2 - A resveratrol structural modification

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AU - Melody, Noeleen

AU - Thornhill, Andrew

AU - Knight, John C.

AU - Groy, Thomas L.

AU - Herald, Cherry L.

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AB - 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.

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Antineoplastic agents. 579. Synthesis and cancer cell growth evaluation of E-stilstatin 3: A resveratrol structural modification

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CCDC 736738: Experimental Crystal Structure Determination

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Antineoplastic agents. 579. Synthesis and cancer cell growth evaluation of E-stilstatin 3: A resveratrol structural modification

Abstract

ASJC Scopus subject areas

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CCDC 736738: Experimental Crystal Structure Determination

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