Synthesis of chamaecypanone C analogues from in situ-generated cyclopentadienones and their biological evaluation

Suwei Dong; Tian Qin; Ernest Hamel; John A. Beutler; John A. Porco

doi:10.1021/ja3084708

Synthesis of chamaecypanone C analogues from in situ-generated cyclopentadienones and their biological evaluation

Suwei Dong, Tian Qin, Ernest Hamel, John A. Beutler, John A. Porco

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

30 Scopus citations

Abstract

A rhodium-catalyzed dehydrogenation protocol for the conversion of 3,5-diarylcyclopentenones to the corresponding 2,4-diarylcyclopentadienones has been developed. With this protocol, analogues of the cytotoxic agent chamaecypanone C have been synthesized via Diels-Alder cycloaddition between the cyclopentadienones and in situ-generated o-quinols. Biological evaluation of these analogues revealed a compound with higher activity as a microtubule inhibitor and cytotoxic agent in comparison with the parent structure.

Original language	English (US)
Pages (from-to)	19782-19787
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	134
Issue number	48
DOIs	https://doi.org/10.1021/ja3084708
State	Published - Dec 5 2012
Externally published	Yes

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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abstract = "A rhodium-catalyzed dehydrogenation protocol for the conversion of 3,5-diarylcyclopentenones to the corresponding 2,4-diarylcyclopentadienones has been developed. With this protocol, analogues of the cytotoxic agent chamaecypanone C have been synthesized via Diels-Alder cycloaddition between the cyclopentadienones and in situ-generated o-quinols. Biological evaluation of these analogues revealed a compound with higher activity as a microtubule inhibitor and cytotoxic agent in comparison with the parent structure.",

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AU - Dong, Suwei

AU - Qin, Tian

AU - Hamel, Ernest

AU - Beutler, John A.

AU - Porco, John A.

PY - 2012/12/5

Y1 - 2012/12/5

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AB - A rhodium-catalyzed dehydrogenation protocol for the conversion of 3,5-diarylcyclopentenones to the corresponding 2,4-diarylcyclopentadienones has been developed. With this protocol, analogues of the cytotoxic agent chamaecypanone C have been synthesized via Diels-Alder cycloaddition between the cyclopentadienones and in situ-generated o-quinols. Biological evaluation of these analogues revealed a compound with higher activity as a microtubule inhibitor and cytotoxic agent in comparison with the parent structure.

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Synthesis of chamaecypanone C analogues from in situ-generated cyclopentadienones and their biological evaluation

Abstract

ASJC Scopus subject areas

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