Intermolecular interactions in the crystal structures of potential HIV-1 integrase inhibitors.
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.
Majerz-Maniecka
Katarzyna
K
Faculty of Chemistry, Jagiellonian University, ul. R. Ingardena 3, 30-060 Kraków, Poland. majerz@chemia.uj.edu.pl
Musiol
Robert
R
Nitek
Wojciech
W
Oleksyn
Barbara J
BJ
Mouscadet
Jean-Francois
JF
Le Bret
Marc
M
Polanski
Jaroslaw
J
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
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