title: Structure-activity relationships in quinoline Reissert derivatives with HIV-1 reverse transcriptase inhibitory activity.
abstract: The relationship between the chemical structure and the HIV-1 RT inhibitory activity has been studied for a series of quinoline derivatives. Two methods were used: a standard QSAR analysis, by combining the methods of Hansch and Free-Wilson, and an analysis using quantum chemistry indices as descriptor parameters, by the semiempirical method AM1. The equations obtained lead to the proposal that the activity of the compounds increases, mainly, with the presence of electron-withdrawing substituents in position 6 of the quinoline ring that cause a decrease in the energy from the molecular orbital LUMO. In turn, this fact leads to the proposal that the most important interaction of these compounds with the HIV-1 RT is a charge transfer type interaction, with the quinoline aromatic ring acting as acceptor.
authors.affiliation: Dpt. of Medicinal Chemistry, Centro de Investigación en Farmacobiologia Aplicada, Universidad de Navarra, Pamplona, España.
authors.forename: M
authors.initials: M
authors.lastname: Font
authors.forename: A
authors.initials: A
authors.lastname: Monge
authors.forename: I
authors.initials: I
authors.lastname: Ruiz
authors.forename: B
authors.initials: B
authors.lastname: Heras
mesh_terms: D019380:Anti-HIV Agents / Q000494:pharmacology*; D054303:HIV Reverse Transcriptase / Q000037:antagonists & inhibitors*; D008958:Models, Molecular; D008968:Molecular Conformation; D011804:Quinolines / Q000494:pharmacology*; D018894:Reverse Transcriptase Inhibitors / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D019380:Anti-HIV Agents; D011804:Quinolines; D018894:Reverse Transcriptase Inhibitors; D054303:HIV Reverse Transcriptase