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

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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

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Keywords

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

ASJC Scopus subject areas

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

Cite this

Meanwell, N. A., Wallace, O. B., Wang, H., Deshpande, M., Pearce, B. C., Trehan, A., Yeung, K. S., Qiu, Z., Wright, J. J. K., Robinson, B. A., Gong, Y. F., Wang, H. G. H., Blair, W. S., Shi, P. Y., & Lin, P. F. (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, 19(17), 5136-5139. https://doi.org/10.1016/j.bmcl.2009.07.027