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

Maiti A, Reddy PV, Sturdy M, Marler L, Pegan SD, Mesecar AD, Pezzuto JM, Cushman M
J Med Chem 52 1873-84 (2009)
Cited: 29 times
EuropePMC logo PMID: 19265439

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.

Articles - 3g5m mentioned but not cited (1)

  1. Aromatase and glycosyl transferase inhibiting acridone alkaloids from fruits of Cameroonian Zanthoxylum species. Wouatsa VN, Misra L, Kumar S, Prakash O, Khan F, Tchoumbougnang F, Venkatesh RK. Chem Cent J 7 125 (2013)


Reviews citing this publication (3)

  1. Recent Progress in the Discovery of Next Generation Inhibitors of Aromatase from the Structure-Function Perspective. Ghosh D, Lo J, Egbuta C. J Med Chem 59 5131-5148 (2016)
  2. Combating breast cancer with non-steroidal aromatase inhibitors (NSAIs): Understanding the chemico-biological interactions through comparative SAR/QSAR study. Adhikari N, Amin SA, Saha A, Jha T. Eur J Med Chem 137 365-438 (2017)
  3. Natural compounds with aromatase inhibitory activity: an update. Balunas MJ, Kinghorn AD. Planta Med 76 1087-1093 (2010)

Articles citing this publication (25)



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