Abstract
Conformational analysis of the 3-benzylpiperidine in CCR3 antagonist clinical candidate 1 (BMS-639623) predicts that the benzylpiperidine may be replaced by acyclic, conformationally stabilized, anti-1,2-disubstituted phenethyl- and phenpropylamines. Ab initio calculations, enantioselective syntheses, and evaluation in CCR3 binding and chemotaxis assays of anti-1-methyl-2-hydroxyphenethyl- and phenpropylamine-containing CCR3 antagonists support this conformational correlation. © 2007 Elsevier Ltd. All rights reserved.
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Gardner, D. S., Santella, J. B., Tebben, A. J., Batt, D. G., Ko, S. S., Traeger, S. C., … Duncia, J. V. (2008). From rigid cyclic templates to conformationally stabilized acyclic scaffolds. Part II: Acyclic replacements for the (3S)-3-benzylpiperidine in a series of potent CCR3 antagonists. Bioorganic and Medicinal Chemistry Letters, 18(2), 586–595. https://doi.org/10.1016/j.bmcl.2007.11.087
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