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

doi:10.1016/j.bmcl.2009.07.027

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

Biochemistry & Molecular Biology

Research output: Contribution to journal › Article › peer-review

41 Scopus citations

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 language	English (US)
Pages (from-to)	5136-5139
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	19
Issue number	17
DOIs	https://doi.org/10.1016/j.bmcl.2009.07.027
State	Published - Sep 1 2009

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

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10.1016/j.bmcl.2009.07.027

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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

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, PY & 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

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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.",

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AU - Deshpande, Milind

AU - Pearce, Bradley C.

AU - Trehan, Ashok

AU - Yeung, Kap Sun

AU - Qiu, Zhilei

AU - Wright, J. J.Kim

AU - Robinson, Brett A.

AU - Gong, Yi Fei

AU - Wang, Hwei Gene Heidi

AU - Blair, Wade S.

AU - Shi, Pei Yong

AU - Lin, Pin fang

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AB - 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.

KW - Antiviral

KW - HIV attachment inhibitor

KW - HIV inhibitor

KW - Indole glyoxamide

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Inhibitors of HIV-1 attachment. Part 3: A preliminary survey of the effect of structural variation of the benzamide moiety on antiviral activity

Abstract

Keywords

ASJC Scopus subject areas

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