Synthesis of Secondary Amines of Bornylamine and Isobornylamine Containing a Saturated N-Heterocycle and Study of Their Antiviral Activity against Respiratory Syncytial Virus

Abstract

Natural compounds are actively used as promising starting molecules for the development of new antiviral drugs. In this paper, a method was proposed for the synthesis of new derivatives of bicyclic monoterpenoids using endo- and exo-bornylamines as starting materials. It was shown that alkylation of (+)-exo-bornylamine and (+)- or (–)-endo-bornylamine with 2-chloro-1-morpholinoethanone, 2-chloro-1-(piperidin-1-yl)ethanone and 2-chloro-1-(4-methylpiperidin-1-yl)ethanone in the presence of potassium carbonate as a base leads to the corresponding secondary amines. In order to study the effect of the amide group on the antiviral activity, some of the prepared compounds were reduced to amines. It was found that the exo-bornylamine derivative containing the 4-methylpiperidine fragment has pronounced antiviral activity against the respiratory syncytial virus.