title: Synthesis and evaluation of new Reissert analogs as HIV-1 reverse transcriptase inhibitors. 1. Quinoline and quinoxaline derivatives.
abstract: The synthesis and preliminary evaluation of new quinoline and quinoxaline derivatives (obtained by applying the original Reissert method, conveniently modified) as HIV-1 Reverse Transcriptase (RT) inhibitors are presented in this paper; likewise, the first structure-activity relationships are also proposed. Propyl 2-cyano-1(2H)-quinolin-carboxylate 2e, isopropyl 2-cyano-1 (2H)-quinolincarboxylate 2f, butyl 2-cyano-1 (2H)-quinolincarboxylate 2g and isobutyl 2-cyano-1 (2H)-quinolincarboxylate 2h have been selected as lead compounds. These compounds are active against the HIV-1 RT mutant type P236L (2f, IC50 = 1.2 microM) and present activity as anti-infective agents in HLT41acZ-1IIIB cells, showing no cytotoxicity at the active concentrations.
authors.affiliation: Medicinal Chemistry, Universidad de Navarra, Pamplona, Spain.
authors.forename: M
authors.initials: M
authors.lastname: Font
authors.forename: A
authors.initials: A
authors.lastname: Monge
authors.forename: E
authors.initials: E
authors.lastname: Alvarez
authors.forename: A
authors.initials: A
authors.lastname: Cuartero
authors.forename: M J
authors.initials: MJ
authors.lastname: Losa
authors.forename: M J
authors.initials: MJ
authors.lastname: Fidalgo
authors.forename: C
authors.initials: C
authors.lastname: SanMartín
authors.forename: E
authors.initials: E
authors.lastname: Nadal
authors.forename: I
authors.initials: I
authors.lastname: Ruiz
authors.forename: I
authors.initials: I
authors.lastname: Merino
authors.forename: J J
authors.initials: JJ
authors.lastname: Martínez-Irujo
authors.forename: E
authors.initials: E
authors.lastname: Alberdi
authors.forename: E
authors.initials: E
authors.lastname: Santiago
authors.forename: I
authors.initials: I
authors.lastname: Prieto
authors.forename: J J
authors.initials: JJ
authors.lastname: Lasarte
authors.forename: P
authors.initials: P
authors.lastname: Sarobe
authors.forename: F
authors.initials: F
authors.lastname: Borrás
mesh_terms: D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002460:Cell Line; D054303:HIV Reverse Transcriptase / Q000037:antagonists & inhibitors*; D006801:Humans; D011804:Quinolines / Q000138:chemical synthesis* / Q000494:pharmacology; D011810:Quinoxalines / Q000138:chemical synthesis* / Q000494:pharmacology; D018894:Reverse Transcriptase Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D019380:Anti-HIV Agents; D011804:Quinolines; D011810:Quinoxalines; D018894:Reverse Transcriptase Inhibitors; D054303:HIV Reverse Transcriptase