title: Intermolecular interactions in the crystal structures of potential HIV-1 integrase inhibitors.
abstract: 2-[(2,5-dichloro-4-nitro-phenylamino)-methoxy-methyl]-8-hydroxy-quinoline 1 and 2-methyl-quinoline-5,8-dione-5-oxime 2 were obtained as potential HIV-1 integrase inhibitors and analyzed by X-ray crystallography. Semiempirical theoretical calculations of energy preferred conformations were also carried out. The crystal structures of both compounds are stabilized via hydrogen bonds and pi-pi stacking interactions. The planarity of compound 1 is caused by intramolecular hydrogen bonds.
authors.affiliation: Faculty of Chemistry, Jagiellonian University, ul. R. Ingardena 3, 30-060 Kraków, Poland. majerz@chemia.uj.edu.pl
authors.forename: Katarzyna
authors.initials: K
authors.lastname: Majerz-Maniecka
authors.forename: Robert
authors.initials: R
authors.lastname: Musiol
authors.forename: Wojciech
authors.initials: W
authors.lastname: Nitek
authors.forename: Barbara J
authors.initials: BJ
authors.lastname: Oleksyn
authors.forename: Jean-Francois
authors.initials: JF
authors.lastname: Mouscadet
authors.forename: Marc
authors.initials: M
authors.lastname: Le Bret
authors.forename: Jaroslaw
authors.initials: J
authors.lastname: Polanski
mesh_terms: D003460:Crystallization; D018360:Crystallography, X-Ray; D019427:HIV Integrase / Q000187:drug effects*; D019428:HIV Integrase Inhibitors / Q000737:chemistry* / Q000494:pharmacology*; D008958:Models, Molecular; D015394:Molecular Structure; D011804:Quinolines / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: C509749:2-((2,5-dichloro-4-nitrophenylamino)methoxymethyl)8-hydroxyquinoline; C509750:2-methylquinoline-5,8-dione-5-oxime; D019428:HIV Integrase Inhibitors; D011804:Quinolines; D019427:HIV Integrase