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 journalArticle

19 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)19782-19787
Number of pages6
JournalJournal of the American Chemical Society
Volume134
Issue number48
DOIs
StatePublished - Dec 5 2012
Externally publishedYes

Fingerprint

Cytotoxins
Hydroquinones
Rhodium
Cycloaddition
Cycloaddition Reaction
Dehydrogenation
Microtubules
chamaecypanone C

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Synthesis of chamaecypanone C analogues from in situ-generated cyclopentadienones and their biological evaluation. / Dong, Suwei; Qin, Tian; Hamel, Ernest; Beutler, John A.; Porco, John A.

In: Journal of the American Chemical Society, Vol. 134, No. 48, 05.12.2012, p. 19782-19787.

Research output: Contribution to journalArticle

Dong, Suwei ; Qin, Tian ; Hamel, Ernest ; Beutler, John A. ; Porco, John A. / Synthesis of chamaecypanone C analogues from in situ-generated cyclopentadienones and their biological evaluation. In: Journal of the American Chemical Society. 2012 ; Vol. 134, No. 48. pp. 19782-19787.
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