title: Chiral NG-acylated hetarylpropylguanidine-type histamine H2 receptor agonists do not show significant stereoselectivity.
abstract: A set of chiral imidazolylpropylguanidines and 2-aminothiazolylpropylguanidines bearing N(G)-3-phenyl- or N(G)-3-cyclohexylbutanoyl residues was synthesized and investigated for histamine H(2) receptor (H(2)R) agonism (guinea pig (gp) right atrium, GTPase assay on recombinant gp and human (h)H(2)R) and for hH(2)R selectivity compared to hH(1)R, hH(3)R and hH(4)R. In contrast to previous studies on arpromidine derivatives, the present investigation of acylguanidine-type compounds revealed only very low eudismic ratios (1.1-3.2), indicating the stereochemistry of the acyl moiety to play only a minor role in this series of H(2)R agonists.
authors.affiliation: Institute of Pharmacy, Pharmaceutical/Medicinal Chemistry, University of Regensburg, D-93040 Regensburg, Germany.
authors.forename: Prasanta
authors.initials: P
authors.lastname: Ghorai
authors.forename: Anja
authors.initials: A
authors.lastname: Kraus
authors.forename: Tobias
authors.initials: T
authors.lastname: Birnkammer
authors.forename: Roland
authors.initials: R
authors.lastname: Geyer
authors.forename: Günther
authors.initials: G
authors.lastname: Bernhardt
authors.forename: Stefan
authors.initials: S
authors.lastname: Dove
authors.forename: Roland
authors.initials: R
authors.lastname: Seifert
authors.forename: Sigurd
authors.initials: S
authors.lastname: Elz
authors.forename: Armin
authors.initials: A
authors.lastname: Buschauer
mesh_terms: D000818:Animals; D006146:Guanidines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006168:Guinea Pigs; D017442:Histamine Agonists / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D006801:Humans; D011970:Receptors, Histamine H2 / Q000737:chemistry* / Q000235:genetics / Q000378:metabolism; D011994:Recombinant Proteins / Q000737:chemistry / Q000235:genetics / Q000378:metabolism; D013237:Stereoisomerism
chemical_list: D006146:Guanidines; D017442:Histamine Agonists; D011970:Receptors, Histamine H2; D011994:Recombinant Proteins; C031653:propylguanidine