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ID: ALA1137845

Journal: Bioorg Med Chem Lett

Title: Discovery of N-propylurea 3-benzylpiperidines as selective CC chemokine receptor-3 (CCR3) antagonists.

Authors: Varnes JG, Gardner DS, Santella JB, Duncia JV, Estrella M, Watson PS, Clark CM, Ko SS, Welch P, Covington M, Stowell N, Wadman E, Davies P, Solomon K, Newton RC, Trainor GL, Decicco CP, Wacker DA.

Abstract: The discovery of novel and selective small molecule antagonists of the CC Chemokine Receptor-3 (CCR3) is presented. Simple conversion from a 4- to 3-benzylpiperidine gave improved selectivity for CCR3 over the serotonin 5HT(2A) receptor. Chiral resolution and exploration of mono- and disubstitution of the N-propylurea resulted in several 3-benzylpiperidine N-propylureas with CCR3 binding IC(50)s under 5 nM. Data from in vitro calcium mobilization and chemotaxis assays for these compounds ranged from high picomolar to low nanomolar EC(50)s and correlated well with antagonist binding IC(50)s.

CiteXplore: 15026042

DOI: 10.1016/j.bmcl.2004.01.059