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

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.

SUBMITTER: Maiti A

PROVIDER: S-EPMC2673050 | biostudies-literature | 2009 Apr

REPOSITORIES: biostudies-literature

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

Maiti Arup A Reddy P V Narasimha PV Sturdy Megan M Marler Laura L Pegan Scott D SD Mesecar Andrew D AD Pezzuto John M JM Cushman Mark M

Journal of medicinal chemistry 20090401 7

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 ...[more]

PMID: 19265439

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