Literature DB >> 13678401

Discovery of 4-benzoyl-1-[(4-methoxy-1H- pyrrolo[2,3-b]pyridin-3-yl)oxoacetyl]-2- (R)-methylpiperazine (BMS-378806): a novel HIV-1 attachment inhibitor that interferes with CD4-gp120 interactions.

Tao Wang1, Zhongxing Zhang, Owen B Wallace, Milind Deshpande, Haiquan Fang, Zheng Yang, Lisa M Zadjura, Donald L Tweedie, Stella Huang, Fang Zhao, Sunanda Ranadive, Brett S Robinson, Yi-Fei Gong, Keith Ricarrdi, Timothy P Spicer, Carol Deminie, Ronald Rose, Hwei-Gene Heidi Wang, Wade S Blair, Pei-Yong Shi, Pin-Fang Lin, Richard J Colonno, Nicholas A Meanwell.   

Abstract

Indole derivative 1 interferes with the interaction of the HIV surface protein gp120 with the host cell receptor CD4. The 4-fluoro derivative 2 exhibited markedly enhanced potency and was bioavailable in the rat, dog, and cynomolgus monkey when administered orally as a solution formulation. However, aqueous suspensions of 2 were poorly bioavailable, indicative of dissolution-limited absorption. The 7-azaindole derivative 3, BMS-378806, exhibited improved pharmaceutical properties while retaining the HIV-1 inhibitory profile of 2.

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Year:  2003        PMID： 13678401     DOI： 10.1021/jm034082o

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  57 in total

1.  In vitro antiviral characteristics of HIV-1 attachment inhibitor BMS-626529, the active component of the prodrug BMS-663068.

Authors:  Beata Nowicka-Sans; Yi-Fei Gong; Brian McAuliffe; Ira Dicker; Hsu-Tso Ho; Nannan Zhou; Betsy Eggers; Pin-Fang Lin; Neelanjana Ray; Megan Wind-Rotolo; Li Zhu; Antara Majumdar; David Stock; Max Lataillade; George J Hanna; John D Matiskella; Yasutsugu Ueda; Tao Wang; John F Kadow; Nicholas A Meanwell; Mark Krystal
Journal:  Antimicrob Agents Chemother       Date:  2012-04-30       Impact factor: 5.191

2.  Antiviral activity, pharmacokinetics, and safety of BMS-488043, a novel oral small-molecule HIV-1 attachment inhibitor, in HIV-1-infected subjects.

Authors:  George J Hanna; Jacob Lalezari; James A Hellinger; David A Wohl; Richard Nettles; Anna Persson; Mark Krystal; Pinfang Lin; Richard Colonno; Dennis M Grasela
Journal:  Antimicrob Agents Chemother       Date:  2010-11-15       Impact factor: 5.191

3.  Thermodynamics of binding of a low-molecular-weight CD4 mimetic to HIV-1 gp120.

Authors:  Arne Schön; Navid Madani; Jeffrey C Klein; Amy Hubicki; Danny Ng; Xinzhen Yang; Amos B Smith; Joseph Sodroski; Ernesto Freire
Journal:  Biochemistry       Date:  2006-09-12       Impact factor: 3.162

4.  Restraining the conformation of HIV-1 gp120 by removing a flexible loop.

Authors:  Sophia Rits-Volloch; Gary Frey; Stephen C Harrison; Bing Chen
Journal:  EMBO J       Date:  2006-09-28       Impact factor: 11.598

5.  Inhibition of envelope-mediated CD4+-T-cell depletion by human immunodeficiency virus attachment inhibitors.

Authors:  Louis Alexander; Sharon Zhang; Brian McAuliffe; David Connors; Nannon Zhou; Tao Wang; Michele Agler; John Kadow; Pin-Fang Lin
Journal:  Antimicrob Agents Chemother       Date:  2009-08-31       Impact factor: 5.191

6.  Structure-activity relationships in the binding of chemically derivatized CD4 to gp120 from human immunodeficiency virus.

Authors:  Hui Xie; Danny Ng; Sergey N Savinov; Barna Dey; Peter D Kwong; Richard Wyatt; Amos B Smith; Wayne A Hendrickson
Journal:  J Med Chem       Date:  2007-09-06       Impact factor: 7.446

7.  Long-Acting BMS-378806 Analogues Stabilize the State-1 Conformation of the Human Immunodeficiency Virus Type 1 Envelope Glycoproteins.

Authors:  Shitao Zou; Shijian Zhang; Althea Gaffney; Haitao Ding; Maolin Lu; Jonathan R Grover; Mark Farrell; Hanh T Nguyen; Connie Zhao; Saumya Anang; Meiqing Zhao; Mohammadjavad Mohammadi; Scott C Blanchard; Cameron Abrams; Navid Madani; Walther Mothes; John C Kappes; Amos B Smith; Joseph Sodroski
Journal:  J Virol       Date:  2020-05-04       Impact factor: 5.103

8.  Adaptation of HIV-1 to cells with low expression of the CCR5 coreceptor.

Authors:  Nicole Espy; Beatriz Pacheco; Joseph Sodroski
Journal:  Virology       Date:  2017-05-15       Impact factor: 3.616

9.  Use of the quartz crystal microbalance to monitor ligand-induced conformational rearrangements in HIV-1 envelope protein gp120.

Authors:  Hyun-Su Lee; Mark Contarino; M Umashankara; Arne Schön; Ernesto Freire; Amos B Smith; Irwin M Chaiken; Lynn S Penn
Journal:  Anal Bioanal Chem       Date:  2009-12-17       Impact factor: 4.142

10.  An antibody-recruiting small molecule that targets HIV gp120.

Authors:  Christopher G Parker; Robert A Domaoal; Karen S Anderson; David A Spiegel
Journal:  J Am Chem Soc       Date:  2009-11-18       Impact factor: 15.419
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