Insights from ab initio quantum chemical calculations into the preferred tautomeric forms and binding affinities to CDK2 of substituted pyrazolopyridines

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Abstract

Ab initio calculations were employed to compute pKa values and tautomer properties of a series of substituted pyrazolopyridines. The results show that the neutral 1H tautomer predominates, but upon protonation this proton migrates to give the preferred charged [2H,7H] tautomer. The basicity of the pyrazolopyridines is correlated with the electron donating capability of the 4-substituent. Ab initio free energy calculations were also used to identify determinants of binding affinity for some recently published pyrazolopyridine inhibitors of CDK2. Hydrogen-bonding affinity may be one important component of binding strength.

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