2. Academic Validation
  3. 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

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

  • Bioorg Med Chem Lett. 2008 Jan 15;18(2):586-95. doi: 10.1016/j.bmcl.2007.11.087.
Daniel S Gardner 1,  Joseph B Santella 3rd,  Andrew J Tebben,  Douglas G Batt,  Soo S Ko,  Sarah C Traeger,  Patricia K Welch,  Eric A Wadman,  Paul Davies,  Percy H Carter,  John V Duncia
Affiliations

Affiliation

  • 1 Bristol-Myers Squibb Company, R & D, PO Box 4000, Princeton, NJ 08543-4000, USA.
PMID: 18160284 DOI: 10.1016/j.bmcl.2007.11.087
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.

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