Inhibitors of HIV-1 attachment. Part 3

A preliminary survey of the effect of structural variation of the benzamide moiety on antiviral activity

Nicholas A. Meanwell, Owen B. Wallace, Henry Wang, Milind Deshpande, Bradley C. Pearce, Ashok Trehan, Kap Sun Yeung, Zhilei Qiu, J. J Kim Wright, Brett A. Robinson, Yi Fei Gong, Hwei Gene Heidi Wang, Wade S. Blair, Pei-Yong Shi, Pin fang Lin

Research output: Contribution to journalArticle

29 Citations (Scopus)

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.

Original languageEnglish (US)
Pages (from-to)5136-5139
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume19
Issue number17
DOIs
StatePublished - Sep 1 2009
Externally publishedYes

Fingerprint

CD4 Antigens
Ethane
Antiviral Agents
HIV-1
Substitution reactions
indole
Surveys and Questionnaires
benzamide

Keywords

  • Antiviral
  • HIV attachment inhibitor
  • HIV inhibitor
  • Indole glyoxamide

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery
  • Organic Chemistry
  • Molecular Medicine
  • Molecular Biology
  • Clinical Biochemistry
  • Biochemistry

Cite this

Inhibitors of HIV-1 attachment. Part 3 : A preliminary survey of the effect of structural variation of the benzamide moiety on antiviral activity. / Meanwell, Nicholas A.; Wallace, Owen B.; Wang, Henry; Deshpande, Milind; Pearce, Bradley C.; Trehan, Ashok; Yeung, Kap Sun; Qiu, Zhilei; Wright, J. J Kim; Robinson, Brett A.; Gong, Yi Fei; Wang, Hwei Gene Heidi; Blair, Wade S.; Shi, Pei-Yong; Lin, Pin fang.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 19, No. 17, 01.09.2009, p. 5136-5139.

Research output: Contribution to journalArticle

Meanwell, NA, Wallace, OB, Wang, H, Deshpande, M, Pearce, BC, Trehan, A, Yeung, KS, Qiu, Z, Wright, JJK, Robinson, BA, Gong, YF, Wang, HGH, Blair, WS, Shi, P-Y & Lin, PF 2009, 'Inhibitors of HIV-1 attachment. Part 3: A preliminary survey of the effect of structural variation of the benzamide moiety on antiviral activity', Bioorganic and Medicinal Chemistry Letters, vol. 19, no. 17, pp. 5136-5139. https://doi.org/10.1016/j.bmcl.2009.07.027
Meanwell, Nicholas A. ; Wallace, Owen B. ; Wang, Henry ; Deshpande, Milind ; Pearce, Bradley C. ; Trehan, Ashok ; Yeung, Kap Sun ; Qiu, Zhilei ; Wright, J. J Kim ; Robinson, Brett A. ; Gong, Yi Fei ; Wang, Hwei Gene Heidi ; Blair, Wade S. ; Shi, Pei-Yong ; Lin, Pin fang. / Inhibitors of HIV-1 attachment. Part 3 : A preliminary survey of the effect of structural variation of the benzamide moiety on antiviral activity. In: Bioorganic and Medicinal Chemistry Letters. 2009 ; Vol. 19, No. 17. pp. 5136-5139.
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