6533b85afe1ef96bd12b9f17

RESEARCH PRODUCT

Conformational study of N-alkyl-benzyltetrahydroisoquinolines alkaloid

M.a. ZamoraFernando D. SuvireAlmudena BermejoRicardo D. EnrizDiego CortesInmaculada Andreu

subject

Steric effectschemistry.chemical_classificationStereochemistryAlkaloidAb initioCondensed Matter PhysicsBiochemistryResidue (chemistry)chemistryComputational chemistrySide chainMoleculePhysical and Theoretical ChemistryLone pairAlkyl

description

Abstract 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 C 1 atom were also considered. Our results indicate that different substituents at C 1 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 D 1 -receptor inhibitory activity.

yearjournalcountryeditionlanguage
2003-12-01Journal of Molecular Structure: THEOCHEM
https://doi.org/10.1016/j.theochem.2003.08.019