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.
Publication types
-
Research Support, N.I.H., Extramural
-
Research Support, N.I.H., Intramural
-
Research Support, Non-U.S. Gov't
MeSH terms
-
Bridged Bicyclo Compounds / chemical synthesis*
-
Bridged Bicyclo Compounds / chemistry
-
Bridged Bicyclo Compounds / pharmacology*
-
Catalysis
-
Cyclopentanes / chemistry*
-
Cyclopentanes / pharmacology*
-
Microtubules / drug effects
-
Molecular Structure
-
Rhodium / chemistry*
-
Tubulin Modulators / chemical synthesis*
-
Tubulin Modulators / chemistry
-
Tubulin Modulators / pharmacology*
Substances
-
Bridged Bicyclo Compounds
-
Cyclopentanes
-
Tubulin Modulators
-
chamaecypanone C
-
Rhodium