2(S)-Amino-3-[1H-imidazol-4(5)-yl]propyl cyclohexylmethyl ether dihydrochloride and 2(S)-amino-3-[1H-imidazol-4(5)-yl]propyl 4-bromobenzyl ether dihydrochloride

Abstract

(Cyclohexylmethyloxymethyl)(1H-imidazol-4-iomethyl)-(S)-ammonium dichloride, C(13)H(25)N(3)O(+).2Cl(-), and (4-bromobenzyl)(1H-imidazol-4-iomethyl)-(S)-ammonium dichloride, C(13)H(18)BrN(3)O(+).2Cl(-), are model compounds with different biological activities for evaluation of the histamine H3-receptor activation mechanism. Both title compounds occur in almost similar extended conformations.

A Proton Relay Process as the Mechanism of Activation of the Histamine H3-Receptor Determined by1H NMR and ab Initio Quantum Mechanical Calculations

“…Mechanism of Activation. The partial opposite biological activities of the dicationic compounds 7 and 8 cannot be explained by the X-ray structures as both compounds exist in an almost identical extended conformation . This indicates that the dicationic extended form of the compounds is not responsible for the receptor activation.…”

“…The partial opposite biological activities of the dicationic compounds 7 and 8 cannot be explained by the X-ray structures as both compounds exist in an almost identical extended conformation. 32 This indicates that the dicationic extended form of the compounds is not responsible for the receptor activation. The populations of the folded and the extended conformations are almost equal in solution at physiological pH and temperature based on 1 H NMR experiments (Table 1).…”