Antineoplastic agents. 565. Synthesis of combretastatin D-2 phosphate and dihydro-combretastatin D-2

George Pettit; Peter D. Quistorf; Jeremy A. Fry; Delbert L. Herald; Ernest Hamel; Jean Chapuis

doi:10.1021/np800635h

Antineoplastic agents. 565. Synthesis of combretastatin D-2 phosphate and dihydro-combretastatin D-2

George Pettit, Peter D. Quistorf, Jeremy A. Fry, Delbert L. Herald, Ernest Hamel, Jean Chapuis

Research output: Contribution to journal › Article › peer-review

21 Scopus citations

Abstract

A modified synthetic route to combretastatin D-2 (5) was devised in order to further evaluate its biological activity, for its conversion to phosphate prodrugs (25-28), and as a route to obtaining dihydro-combretastatin D-2 (42). A parallel first total synthesis of dihydro-combretastatin D-2 was completed, proceeding from a saturated 3-phenylpropionic ester intermediate via the Ullmann biaryl ether reaction (39-41). In contrast to the cancer cell growth inhibitory activity exhibited by combretastatin D-2, relatively minor structural modifications (41, 42) caused elimination of those properties.

Original language	English (US)
Pages (from-to)	876-883
Number of pages	8
Journal	Journal of Natural Products
Volume	72
Issue number	5
DOIs	https://doi.org/10.1021/np800635h
State	Published - May 22 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/np800635h

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abstract = "A modified synthetic route to combretastatin D-2 (5) was devised in order to further evaluate its biological activity, for its conversion to phosphate prodrugs (25-28), and as a route to obtaining dihydro-combretastatin D-2 (42). A parallel first total synthesis of dihydro-combretastatin D-2 was completed, proceeding from a saturated 3-phenylpropionic ester intermediate via the Ullmann biaryl ether reaction (39-41). In contrast to the cancer cell growth inhibitory activity exhibited by combretastatin D-2, relatively minor structural modifications (41, 42) caused elimination of those properties.",

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AU - Herald, Delbert L.

AU - Hamel, Ernest

AU - Chapuis, Jean

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Antineoplastic agents. 565. Synthesis of combretastatin D-2 phosphate and dihydro-combretastatin D-2

Abstract

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CCDC 714059: Experimental Crystal Structure Determination

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Antineoplastic agents. 565. Synthesis of combretastatin D-2 phosphate and dihydro-combretastatin D-2

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 714059: Experimental Crystal Structure Determination

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