Conformational and electronic study of homoallylamines with inhibitory properties against polymers of fungal cell wall

S.VILLAGRA; M.VERNINI; A.M RODRIGUEZ; S.ZACCHINO; V.KOUZNETSOV; ENRIZ R.D.

JOURNAL OF MOLECULAR STRUCTURE THEOCHEM

ELSEVIER SCIENCE BV

Lugar: Amsterdam; Año: 2003 vol. 666 p. 587 - 598

0166-1280

A complete conformational analysis of 4-methyl-2-(30-pyridyl)quinoline (I), 4-methyl-2-(30-pyridyl)-1,2,3,4-tetrahydroquinoline (II) and structurally related compounds with known antifungal properties was carried out using ab initio and DFT calculations. Quasi-planar forms were found as the low-energy conformations for compound I. Sixteen conformations, considering the enantiomeric forms, were obtained for compound II. The preferred forms are 2R4S and 2R4R displaying the ring B in a half-chair arrangement. Intermediate structures in the conversion of compound II into compound I were also evaluated.