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Synthesis of chamaecypanone C analogues from in situ-generated cyclopentadienones and their biological evaluation.
- Source :
-
Journal of the American Chemical Society [J Am Chem Soc] 2012 Dec 05; Vol. 134 (48), pp. 19782-7. Date of Electronic Publication: 2012 Nov 20. - Publication Year :
- 2012
-
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.
- Subjects :
- Bridged Bicyclo Compounds chemistry
Catalysis
Microtubules drug effects
Molecular Structure
Tubulin Modulators chemistry
Bridged Bicyclo Compounds chemical synthesis
Bridged Bicyclo Compounds pharmacology
Cyclopentanes chemistry
Cyclopentanes pharmacology
Rhodium chemistry
Tubulin Modulators chemical synthesis
Tubulin Modulators pharmacology
Subjects
Details
- Language :
- English
- ISSN :
- 1520-5126
- Volume :
- 134
- Issue :
- 48
- Database :
- MEDLINE
- Journal :
- Journal of the American Chemical Society
- Publication Type :
- Academic Journal
- Accession number :
- 23110297
- Full Text :
- https://doi.org/10.1021/ja3084708