Conformational study of N-alkyl-benzyltetrahydroisoquinolines alkaloid

F.D.SUVIRE; I.ANDREU; A. BERMEJO; M.A.ZAMORA; D.CORTES; ENRIZ R.D.

JOURNAL OF MOLECULAR STRUCTURE THEOCHEM

ELSEVIER SCIENCE BV

Lugar: Amsterdam; Año: 2003 vol. 666 p. 109 - 116

0166-1280

An exhaustive conformational study on the benzyltetrahydroisoquinolines (BTHIQ) from ab initio (RHF/6-31G(d)) calculations was carried out. The effects of different substituents at chiral C1 atom were also considered. Our results indicate that different substituents at C1 in BTHIQ molecules introduce a significant steric hindrance which, in turn, might be responsible for a conformational restriction favouring or disfavouring the spatial orientation of the lone pairs of N atom allowing or not the electronic attachment with the side chain of Asp residue. These results can serve as an aid for designing suitable structures of BTHIQs for better dopamine D1-receptor inhibitory activity.