title: Inhibitors of HIV-1 attachment. Part 3: A preliminary survey of the effect of structural variation of the benzamide moiety on antiviral activity.
abstract: 1-(4-Benzoylpiperazin-1-yl)-2-(1H-indol-3-yl)ethane-1,2-dione (1a) has been characterized as an inhibitor of HIV-1 attachment that interferes with the interaction of viral gp120 with the host cell receptor CD4. In previous studies, the effect of indole substitution pattern on antiviral activity was probed. In this Letter, the effect of structural variation of the benzamide moiety is described, a study that reveals the potential or the phenyl moiety to be replaced by five-membered heterocyclic rings and a restricted tolerance for the introduction of substituents to the phenyl ring.
authors.affiliation: Department of Chemistry, Bristol-Myers Squibb Research and Development, 5 Research Parkway, Wallingford, CT 06492, USA. Nicholas.Meanwell@bms.com
authors.forename: Nicholas A
authors.initials: NA
authors.lastname: Meanwell
authors.forename: Owen B
authors.initials: OB
authors.lastname: Wallace
authors.forename: Henry
authors.initials: H
authors.lastname: Wang
authors.forename: Milind
authors.initials: M
authors.lastname: Deshpande
authors.forename: Bradley C
authors.initials: BC
authors.lastname: Pearce
authors.forename: Ashok
authors.initials: A
authors.lastname: Trehan
authors.forename: Kap-Sun
authors.initials: KS
authors.lastname: Yeung
authors.forename: Zhilei
authors.initials: Z
authors.lastname: Qiu
authors.forename: J J Kim
authors.initials: JJ
authors.lastname: Wright
authors.forename: Brett A
authors.initials: BA
authors.lastname: Robinson
authors.forename: Yi-Fei
authors.initials: YF
authors.lastname: Gong
authors.forename: Hwei-Gene Heidi
authors.initials: HG
authors.lastname: Wang
authors.forename: Timothy P
authors.initials: TP
authors.lastname: Spicer
authors.forename: Wade S
authors.initials: WS
authors.lastname: Blair
authors.forename: Pei-Yong
authors.initials: PY
authors.lastname: Shi
authors.forename: Pin-fang
authors.initials: PF
authors.lastname: Lin
mesh_terms: D019380:Anti-HIV Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D001549:Benzamides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D002460:Cell Line; D015699:HIV Envelope Protein gp120 / Q000037:antagonists & inhibitors* / Q000378:metabolism; D023581:HIV Fusion Inhibitors / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D006801:Humans; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D010879:Piperazines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D053585:Virus Attachment / Q000187:drug effects*
chemical_list: C544973:1-(4-benozylpiperazin-1-yl)-2-(1H-indol-3-yl)ethane-1,2-dione; D019380:Anti-HIV Agents; D001549:Benzamides; D015699:HIV Envelope Protein gp120; D023581:HIV Fusion Inhibitors; D007211:Indoles; D010879:Piperazines; C514793:gp120 protein, Human immunodeficiency virus 1; C037689:benzamide