Chiral N(G)-acylated hetarylpropylguanidine-type histamine H2 receptor agonists do not show significant stereoselectivity

Ghorai, Prasanta and Kraus, Anja and Birnkammer, Tobias and Geyer, Roland and Bernhardt, Günther and Dove, Stefan and Seifert, Roland and Elz, Sigurd and Buschauer, Armin (2010) Chiral N(G)-acylated hetarylpropylguanidine-type histamine H2 receptor agonists do not show significant stereoselectivity. Bioorganic & Medicinal Chemistry Letters 20 (10), pp. 3173-3176.

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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 H2 receptor (H2R) agonism (guinea pig (gp) right atrium, GTPase assay on recombinant gp and human (h) H2R) and for hH2R selectivity compared to hH1R, hH3R and hH4R. 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 H2R agonists.

Item Type:

Article

Institutions:

Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical/Medicinal Chemistry II (Prof. Buschauer)
Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical/Medicinal Chemistry I (Prof. Elz)

Projects:

GRK 760, Graduiertenkolleg Medizinische Chemie

Identification Number:

Value	Type
10.1016/j.bmcl.2010.03.082	DOI
20409707	PubMed ID

Related URLs:

URL	URL Type
http://www.sciencedirect.com/science/MiamiMultiMediaURL/B6TF9-4YPPPY3-4/B6TF9-4YPPPY3-4-9/5221/html/S0960894X10004130/838bbb3db83fce38f96e20eff3be8934/mmc1.pdf	Supplementary Material

Keywords:

histamine; H2 receptor agonist; chiral; enantiomers; acylguanidine; Sf9 cells

Subjects:

500 Science > 570 Life sciences
500 Science > 540 Chemistry & allied sciences

Status:

Published

Refereed:

Yes, this version has been refereed

Created at the University of Regensburg:

Yes

Owner:

Prof. Armin Buschauer