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ID: ALA1782038

Journal: Eur J Med Chem

Title: Heterocyclic replacement of the central phenyl core of diamine-based histamine H3 receptor antagonists.

Authors: Swanson DM, Shah CR, Lord B, Morton K, Dvorak LK, Mazur C, Apodaca R, Xiao W, Boggs JD, Feinstein M, Wilson SJ, Barbier AJ, Bonaventure P, Lovenberg TW, Carruthers NI.

Abstract: A series of small molecules consisting of a heterocyclic core flanked by two basic functionalities were synthesized and screened for in vitro affinity at the human histamine H(3) receptor (hH(3)R). Nine of the twenty-eight compounds tested were found to possess a hH(3)R K(i) of less than 5 nM and consisted of a diverse range of central hetero-aromatic linkers (pyridine, pyrazine, oxazole, isoxazole, thiazole, furan, thiophene, and pyrrole). One member of this series, (4-isopropyl-piperazin-1-yl)-(6-piperidin-1-ylmethyl-pyridin-3-yl)-methanone (37), was found to be a high affinity, selective antagonist that crosses the blood-brain barrier and occupies H(3) receptors after oral administration in the rat.

CiteXplore: 19577344

DOI: 10.1016/j.ejmech.2009.06.007