ChemInform Abstract: Ureas and Amides Derived from N‐(5‐Norbornen‐2‐ylmethyl)bornan‐2‐exo‐amine with Antiarrhythmic and Other Activities.

Abstract

ChemInform Abstract Coupling of camphor nitrimine (I) with the norbornenylmethylamine (II) yields the imine (III) which is reduced to give the amine (IV). This reacts with the isocyanates (V) or the aromatic acid chlorides (VII), producing the ureas (VI) or the carboxamides (VIII). The antiinflammatory, hypoglycemic, local anesthetic, antiarrhythmic, and hypotensive activities of the compounds (VI) and (VIII) are reported.

hERG stereoselective modulation by mexiletine‐derived ureas: Molecular docking study, synthesis, and biological evaluation

“…The mechanism of action of MC450 is similar to that described for the two previously reported ureas NS-1643 and NS-3623, thus corroborating the role of the urea scaffold as a useful chemotype in the quest for hERG openers. [28] Starting from the observation that the hERG channel is involved in cardiac disorders and very few and even old studies have been devoted to the evaluation of the cardiac activity of ureabased compounds so far, [29][30][31][32][33][34][35] we aimed to explore the cardiovascular effect of MC450, together with its SS enantiomer and the RS (meso) form to gain insight on a possible stereoselective behavior. These compounds were prepared in high optical purity by an alternative and more efficient stereospecific route than what was previously reported for the RR enantiomer.…”

Synthesis and Reactivity of Amines Containing Several Cage-like Fragments

“…Derivatives of bicyclo[2.2.1]-hept-5-en-2-ylmethylamine containing piperidine, pyrrolidine and other moieties resemble by their activity the amines of the Ic group: specific inhibitors have been found among them for the pathogenic flora, tubercle bacillus, and other bacteria [5]. Up till now a single amine with two cage-like fragments was described whose derivatives (Id, R = COCH 3 , CONHAr) possessed anti-arrhythmic, hypoglycemic, and hypotensive activity [6].Taking into account the favorable effect of the bicyclic carbon cage-like structure on the pharmacological characteristics of amines we aimed this research to development of synthetic procedures and to study of reactivity of amines with norbornene and adamantane skeleton, of the dependence of their chemical behavior on the number and relative position of the cage-like fragments. The amines were prepared by reduction with lithium aluminum hydride of adamantanecarboxamides; a similar procedure had been previously used in the synthesis of alkyl-(aralkyl)norbornenylmethylamines [7].…”

“…Derivatives of bicyclo[2.2.1]-hept-5-en-2-ylmethylamine containing piperidine, pyrrolidine and other moieties resemble by their activity the amines of the Ic group: specific inhibitors have been found among them for the pathogenic flora, tubercle bacillus, and other bacteria [5]. Up till now a single amine with two cage-like fragments was described whose derivatives (Id, R = COCH 3 , CONHAr) possessed anti-arrhythmic, hypoglycemic, and hypotensive activity [6].…”