Literature DB >> 19632112

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 Meanwell1, 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, Timothy P Spicer, Wade S Blair, Pei-Yong Shi, Pin-fang Lin.   

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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Year:  2009        PMID: 19632112     DOI: 10.1016/j.bmcl.2009.07.027

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  8 in total

Review 1.  Thermodynamics-based drug design: strategies for inhibiting protein-protein interactions.

Authors:  Arne Schön; Sonia Y Lam; Ernesto Freire
Journal:  Future Med Chem       Date:  2011-07       Impact factor: 3.808

2.  Illuminating HIV gp120-Ligand Recognition through Computationally-Driven Optimization of Antibody-Recruiting Molecules.

Authors:  Christopher G Parker; Markus K Dahlgren; Ran N Tao; Don T Li; Eugene F Douglass; Takuji Shoda; Navneet Jawanda; Krasimir A Spasov; Sangil Lee; Nannan Zhou; Robert A Domaoal; Richard E Sutton; Karen S Anderson; William L Jorgensen; Mark Krystal; David A Spiegel
Journal:  Chem Sci       Date:  2014-06-01       Impact factor: 9.825

Review 3.  The Genesis and Future Prospects of Small Molecule HIV-1 Attachment Inhibitors.

Authors:  Tao Wang; John F Kadow; Nicholas A Meanwell; Mark Krystal
Journal:  Adv Exp Med Biol       Date:  2022       Impact factor: 2.622

4.  Computational design, synthesis and evaluation of new sulphonamide derivatives targeting HIV-1 gp120.

Authors:  Radhika Vangala; Sree Kanth Sivan; Saikiran Reddy Peddi; Vijjulatha Manga
Journal:  J Comput Aided Mol Des       Date:  2019-12-02       Impact factor: 3.686

5.  Chemically Programmed Antibodies AS HIV-1 Attachment Inhibitors.

Authors:  Shinichi Sato; Tsubasa Inokuma; Nobumasa Otsubo; Dennis R Burton; Carlos F Barbas
Journal:  ACS Med Chem Lett       Date:  2013-05-09       Impact factor: 4.345

6.  Homology models of the HIV-1 attachment inhibitor BMS-626529 bound to gp120 suggest a unique mechanism of action.

Authors:  David R Langley; S Roy Kimura; Prasanna Sivaprakasam; Nannan Zhou; Ira Dicker; Brian McAuliffe; Tao Wang; John F Kadow; Nicholas A Meanwell; Mark Krystal
Journal:  Proteins       Date:  2014-12-23

7.  Synthesis of diindolylmethane (DIM) bearing thiadiazole derivatives as a potent urease inhibitor.

Authors:  Muhammad Taha; Fazal Rahim; Aftab Ahmad Khan; El Hassane Anouar; Naveed Ahmed; Syed Adnan Ali Shah; Mohamed Ibrahim; Zainul Amiruddin Zakari
Journal:  Sci Rep       Date:  2020-05-14       Impact factor: 4.379

Review 8.  Innovation in the discovery of the HIV-1 attachment inhibitor temsavir and its phosphonooxymethyl prodrug fostemsavir.

Authors:  Tao Wang; John F Kadow; Nicholas A Meanwell
Journal:  Med Chem Res       Date:  2021-09-28       Impact factor: 1.965

  8 in total

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