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J Med Chem. 2009 Apr 9;52(7):1873-84. doi: 10.1021/jm801335z.

Synthesis of casimiroin and optimization of its quinone reductase 2 and aromatase inhibitory activities.

Author information

1
Department of Medicinal Chemistry and Molecular Pharmacology, School of Pharmacy and Pharmaceutical Sciences, and the Purdue Cancer Center, Purdue University, West Lafayette, Indiana 47907, USA.

Abstract

An efficient method has been developed to synthesize casimiroin (1), a component of the edible fruit of Casimiroa edulis, on a multigram scale in good overall yield. The route was versatile enough to provide an array of compound 1 analogues that were evaluated as QR2 and aromatase inhibitors. In addition, X-ray crystallography studies of QR2 in complex with compound 1 and one of its more potent analogues has provided insight into the mechanism of action of this new series of QR2 inhibitors. The initial biological investigations suggest that compound 1 and its analogues merit further investigation as potential chemopreventive or chemotherapeutic agents.

PMID:
19265439
PMCID:
PMC2673050
DOI:
10.1021/jm801335z
[Indexed for MEDLINE]
Free PMC Article

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