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

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Maiti A, Reddy PV, Sturdy M, Marler L, Pegan SD, Mesecar AD, Pezzuto JM, Cushman M

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

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

PubMed ID

19265439 [ View in PubMed

]

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.

DrugBank Data that Cites this Article

Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Aminoglutethimide	Cytochrome P450 19A1	IC 50 (nM)	270	7.4	37	Details