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ID: ALA1135002

Journal: Bioorg Med Chem Lett

Title: Optimization of a pyrazolo[1,5-a]pyrimidine class of KDR kinase inhibitors: improvements in physical properties enhance cellular activity and pharmacokinetics.

Authors: Fraley ME, Rubino RS, Hoffman WF, Hambaugh SR, Arrington KL, Hungate RW, Bilodeau MT, Tebben AJ, Rutledge RZ, Kendall RL, McFall RC, Huckle WR, Coll KE, Thomas KA.

Abstract: We have introduced solubilizing functionality to a 3,6-disubstituted pyrazolo[1,5-a]pyrimidine series of KDR kinase inhibitors to improve the physical properties of these compounds. The addition of a basic side-chain to the 6-aryl ring, introduction of 3-pyridyl groups, and most significantly, incorporation of a 4-pyridinonyl substituent at the 6-position of the core are modifications that maintain and often enhance the intrinsic potency of this class of inhibitors. Moreover, the improvements in physical properties result in marked increases in cellular activity and more favorable pharmacokinetics in rats. The synthesis and SAR of these compounds are described.

CiteXplore: 12443771

DOI: 10.1016/s0960-894x(02)00827-2