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Optimization of 5-phenyl-3-pyridinecarbonitriles as PKCtheta inhibitors

Diane H Boschelli1, Daniel Wang, Amar S Prashad

  • 1Wyeth Research, Chemical Sciences, 401 N. Middletown Road, Pearl River, NY 10965, United States. bosched@wyeth.com

Bioorganic & Medicinal Chemistry Letters
|May 19, 2009
PubMed

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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...