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• W2081392835 abstract "Abstract Bioisosteric replacement of the guanidino group in arpromidine‐like histamine H 2 receptor (H 2 R) agonists by an acylguanidine moiety is useful for obtaining potent H 2 R agonists with improved oral bioavailability and blood–brain barrier penetration. We show that bioisosteric replacement of the imidazole ring in N G ‐acylated imidazolylpropylguanidines by a 2‐aminothiazol‐5‐yl group resulted in potent H 2 R agonists with much greater selectivity for the human H 2 R over H 3 and H 4 receptors. magnified image The bioisosteric replacement of the guanidino group in arpromidine‐like histamine H 2 receptor (H 2 R) agonists by an acylguanidine moiety is a useful approach to obtain potent H 2 R agonists with improved oral bioavailability and blood–brain barrier penetration. Unfortunately, the selectivity of such N G ‐acylated imidazolylpropylguanidines for the H 2 R is poor, in particular versus histamine H 3 (H 3 R) and H 4 receptors (H 4 R). This drawback appears to depend on the “privileged” imidazolylpropylguanidine structure. The 2‐amino‐4‐methylthiazol‐5‐yl moiety is a bioisostere of the imidazole ring in the moderately potent H 2 R‐selective histamine analogue amthamine. This approach was successfully applied to acylguanidine‐type H 2 R agonists. The aminothiazoles are nearly equipotent to the corresponding imidazoles as H 2 R agonists. Compared with histamine, the potency is increased up to 40‐fold on the guinea pig right atrium, and up to 125‐ and 280‐fold in GTPase assays with human and guinea pig H 2 R–G s α S fusion proteins expressed in Sf9 insect cells, respectively. Docking studies on H 2 R models support the hypothesis that 2‐aminothiazolyl and imidazolyl derivatives interact with H 2 Rs as bioisosteres. In contrast to the imidazoles, the aminothiazoles are devoid of agonistic or relevant antagonistic effects on H 1 , H 3 , and H 4 receptors. Moreover, unlike amthamine, the 4‐methyl group does not significantly contribute to the H 2 R agonism of N G ‐acylated 2‐amino‐4‐methylthiazol‐5‐ylpropylguanidines." @default.
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• W2081392835 date "2009-02-04" @default.
• W2081392835 modified "2023-10-16" @default.
• W2081392835 title "N^G-Acylated Aminothiazolylpropylguanidines as Potent and Selective Histamine H₂Receptor Agonists" @default.
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• W2081392835 doi "https://doi.org/10.1002/cmdc.200800296" @default.
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