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Acylguanidines as bioisosteres of guanidines: N(G)-acylated imidazolylpropylguanidines, a new class of histamine H2 receptor agonists

Ghorai, Prasanta ; Kraus, Anja ; Keller, Max ; Götte, Carsten ; Igel, Patrick ; Schneider, Erich ; Schnell, David ; Bernhardt, Günther ; Dove, Stefan ; Zabel, Manfred ; Elz, Sigurd ; Seifert, Roland ; Buschauer, Armin


N(1)-Aryl(heteroaryl)alkyl-N(2)-[3-(1H-imidazol-4-yl)propyl]guanidines are potent histamine H2-receptor (H2R) agonists, but their applicability is compromised by the lack of oral bioavailability and CNS penetration. To improve pharmacokinetics, we introduced carbonyl instead of methylene adjacent to the guanidine moiety, decreasing the basicity of the novel H2R agonists by 4-5 orders of ...


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