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Bioorg Med Chem. 2012 Apr 1;20(7):2427-34. doi: 10.1016/j.bmc.2012.01.047. Epub 2012 Feb 11.

Optimization of the aromatase inhibitory activities of pyridylthiazole analogues of resveratrol.

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Department of Medicinal Chemistry and Molecular Pharmacology, College of Pharmacy, and Purdue Center for Cancer Research, Purdue University, West Lafayette, IN 47907, United States.


Aromatase is an established target not only for breast cancer chemotherapy, but also for breast cancer chemoprevention. The moderate and non-selective aromatase inhibitory activity of resveratrol (1) was improved about 100-fold by replacement of the ethylenic bridge with a thiadiazole and the phenyl rings with pyridines (e.g., compound 3). The aromatase inhibitory activity was enhanced over 6000-fold by using a 1,3-thiazole as the central ring and modifying the substituents on the 'A' ring to target the Met374 residue of aromatase. On the other hand, targeting the hydroxyl group of Thr310 by a hydrogen-bond acceptor on the 'B' ring did not improve the aromatase inhibitory activity.

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