Quantum Chemical Study of the Structure and Properties of a Quinolysine Alkaloid Derivative Molecule

Abstract

Derivatives of quinolisidine alkaloids obtained from plants of the genus Lupinus and Anabasis is one of such
important compounds from the point of view of searching for new biologically active substances. The presence
of the primary alcoholic group allows obtaining various modifications of lupinin derivatives. The task of
complex study of the spatial structure of quinolisidine derivatives molecules, pathways and obstacles of their
conformational transitions, conformational states, and reactivity data remains relevant. Therefore, in continuation
of the study of the conformational states of these derivatives, quantum-chemical calculations of the
molecule 1-((4-(4-(m-tolyl)-1H-1,2,3-triazol-1-yl)methyl)octahydro-1H-quinolysine were performed. Geometrical
properties of this molecule, obtained as a result of quantum chemical calculations, were analyzed and
compared with experimental data of X-ray diffraction analysis. According to the results of the conformational
analysis, conducted by rotating along the labile C12-C13 and C10-N2 bonds, the most favorable conformational
states of the molecule were determined. It was shown that the localization of the boundary molecular
orbitals falls on the 1-ethyl-4-(m-tolyl)-1H-1,2,3-triazole substituent at C12 and C10 atoms, which suggests
its participation in the subsequent modification reactions carried out in the search for new biologically active
substances.