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

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.

SUBMITTER: Dong S

PROVIDER: S-EPMC3542833 | biostudies-literature | 2012 Dec

REPOSITORIES: biostudies-literature

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

Dong Suwei S Qin Tian T Hamel Ernest E Beutler John A JA Porco John A JA

Journal of the American Chemical Society 20121120 48

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 ...[more]

PMID: 23110297

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