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Structure-based optimization of pyrazolo-pyrimidine and -pyridine inhibitors of PI3-kinase

Steven T Staben1, Timothy P Heffron, Daniel P Sutherlin

  • 1Discovery Chemistry, Genentech, Inc., South San Francisco, CA 94080, USA. stevents@gene.com

Bioorganic & Medicinal Chemistry Letters
|September 9, 2010
PubMed

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Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).