title: 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.
authors.affiliation: Department of Chemistry and Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, United States.
authors.forename: Suwei
authors.initials: S
authors.lastname: Dong
authors.forename: Tian
authors.initials: T
authors.lastname: Qin
authors.forename: Ernest
authors.initials: E
authors.lastname: Hamel
authors.forename: John A
authors.initials: JA
authors.lastname: Beutler
authors.forename: John A
authors.initials: JA
authors.lastname: Porco
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002384:Catalysis; D003517:Cyclopentanes / Q000737:chemistry* / Q000494:pharmacology*; D008870:Microtubules / Q000187:drug effects; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*; D050257:Tubulin Modulators / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D001643:Bridged Bicyclo Compounds; D003517:Cyclopentanes; D050257:Tubulin Modulators; C539295:chamaecypanone C; D012238:Rhodium