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• W2113217775 abstract "Various approaches to the synthesis of all four stereoisomers of 2-(1H-imidazol-4-yl)cyclopropylamine (cyclopropylhistamine) are described. The rapid and convenient synthesis and resolution of trans-cyclopropylhistamine is reported. The absolute configuration of its enantiomers was determined by single-crystal X-ray crystallographic analysis. The distinct trans-cyclopropylhistamine enantiomers were tested for their activity and affinity on the histamine H3 receptor. (1S,2S)-Cyclopropylhistamine (VUF 5297) acts as an agonist both on the rat cortex (pD2 = 7.1; α = 0.75) and on guinea pig jejunum (pD2 = 6.6; α = 0.75). Its enantiomer, (1R,2R)-cyclopropylhistamine (VUF 5296), is about 1 order of magnitude less active. Both enantiomers show weak activity on H1 and H2 receptors. All synthetic attempts to cis-cyclopropylhistamine were unsuccessful. Nevertheless, the results of this study provide an ideal template for molecular modeling studies of histamine H3 receptor ligands." @default.
• W2113217775 created "2016-06-24" @default.
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• W2113217775 date "1999-03-12" @default.
• W2113217775 modified "2023-10-17" @default.
• W2113217775 title "Characterization of the Binding Site of the Histamine H₃ Receptor. 1. Various Approaches to the Synthesis of 2-(1<i>H</i>-Imidazol-4-yl)cyclopropylamine and Histaminergic Activity of (1<i>R</i>,2<i>R</i>)- and (1<i>S</i>,2<i>S</i>)-2-(1<i>H</i>-Imidazol-4-yl)- cyclopropylamine" @default.
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• W2113217775 doi "https://doi.org/10.1021/jm9810912" @default.
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