title: Structure-activity relationship study of phenylpyrazole derivatives as a novel class of anti-HIV agents.
abstract: The structure-activity relationship of phenylpyrazole derivative 1 was investigated for the development of novel anti-HIV agents. Initial efforts revealed that the diazenyl group can be replaced by an aminomethylene group. In addition, we synthesized various derivatives by the reductive amination of benzaldehydes with 5-aminopyrazoles and carried out parallel structural optimization on the benzyl group and the pyrazole ring. This optimization led to a six-fold more potent derivative 32j than the lead compound 1, and this derivative has a 3',4'-dichloro-(1,1'-biphenyl)-3-yl group.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyoto University, Kyoto 606-8501, Japan.
authors.forename: Tsukasa
authors.initials: T
authors.lastname: Mizuhara
authors.forename: Takayuki
authors.initials: T
authors.lastname: Kato
authors.forename: Atsushi
authors.initials: A
authors.lastname: Hirai
authors.forename: Hideki
authors.initials: H
authors.lastname: Kurihara
authors.forename: Yasuhiro
authors.initials: Y
authors.lastname: Shimada
authors.forename: Masahiko
authors.initials: M
authors.lastname: Taniguchi
authors.forename: Hideki
authors.initials: H
authors.lastname: Maeta
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Togami
authors.forename: Kazuya
authors.initials: K
authors.lastname: Shimura
authors.forename: Masao
authors.initials: M
authors.lastname: Matsuoka
authors.forename: Shiho
authors.initials: S
authors.lastname: Okazaki
authors.forename: Tomoki
authors.initials: T
authors.lastname: Takeuchi
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Ohno
authors.forename: Shinya
authors.initials: S
authors.lastname: Oishi
authors.forename: Nobutaka
authors.initials: N
authors.lastname: Fujii
mesh_terms: D019380:Anti-HIV Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006678:HIV / Q000187:drug effects; D020128:Inhibitory Concentration 50; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D019380:Anti-HIV Agents; D001555:Benzene Derivatives; D011720:Pyrazoles
keywords: Anti-HIV agent; HIV; NNRTI; NRTI; PI; Phenylpyrazole; human immunodeficiency virus; non-nucleoside reverse transcriptase inhibitor; nucleoside reverse transcriptase inhibitor; protease inhibitor