Literature DB >> 27994756

Design, Conformation, and Crystallography of 2-Naphthyl Phenyl Ethers as Potent Anti-HIV Agents.

Won-Gil Lee1, Albert H Chan2, Krasimir A Spasov2, Karen S Anderson2, William L Jorgensen1.   

Abstract

Catechol diethers that incorporate a 7-cyano-2-naphthyl substituent are reported as non-nucleoside inhibitors of HIV-1 reverse transcriptase (NNRTIs). Many of the compounds have 1-10 nM potencies toward wild-type HIV-1. An interesting conformational effect allows two unique conformers for the naphthyl group in complexes with HIV-RT. X-ray crystal structures for 4a and 4f illustrate the alternatives.

Entities:  

Keywords:  Anti-HIV agents; NNRTIs; protein crystallography

Year:  2016        PMID： 27994756      PMCID： PMC5151141          DOI： 10.1021/acsmedchemlett.6b00390

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  20 in total

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Authors:  Edit Baka; John E A Comer; Krisztina Takács-Novák
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Review 2.  HIV-1 NNRTIs: structural diversity, pharmacophore similarity, and implications for drug design.

Authors:  Peng Zhan; Xuwang Chen; Dongyue Li; Zengjun Fang; Erik De Clercq; Xinyong Liu
Journal:  Med Res Rev       Date:  2011-04-26       Impact factor: 12.944

3.  Potent Inhibitors Active against HIV Reverse Transcriptase with K101P, a Mutation Conferring Rilpivirine Resistance.

Authors:  William T Gray; Kathleen M Frey; Sarah B Laskey; Andrea C Mislak; Krasimir A Spasov; Won-Gil Lee; Mariela Bollini; Robert F Siliciano; William L Jorgensen; Karen S Anderson
Journal:  ACS Med Chem Lett       Date:  2015-08-31       Impact factor: 4.345

4.  Computer-aided discovery of anti-HIV agents.

Authors:  William L Jorgensen
Journal:  Bioorg Med Chem       Date:  2016-07-21       Impact factor: 3.641

Review 5.  In search of a treatment for HIV--current therapies and the role of non-nucleoside reverse transcriptase inhibitors (NNRTIs).

Authors:  Chevonne Reynolds; Charles B de Koning; Stephen C Pelly; Willem A L van Otterlo; Moira L Bode
Journal:  Chem Soc Rev       Date:  2012-05-22       Impact factor: 54.564

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Authors:  Adrian S Ray; Zhenjun Yang; Chung K Chu; Karen S Anderson
Journal:  Antimicrob Agents Chemother       Date:  2002-03       Impact factor: 5.191

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Authors:  T S Lin; M Z Luo; M C Liu; S B Pai; G E Dutschman; Y C Cheng
Journal:  Biochem Pharmacol       Date:  1994-01-20       Impact factor: 5.858

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Authors:  William L Jorgensen
Journal:  Acc Chem Res       Date:  2009-06-16       Impact factor: 22.384

10.  Structure-based evaluation of non-nucleoside inhibitors with improved potency and solubility that target HIV reverse transcriptase variants.

Authors:  Kathleen M Frey; David E Puleo; Krasimir A Spasov; Mariella Bollini; William L Jorgensen; Karen S Anderson
Journal:  J Med Chem       Date:  2015-03-05       Impact factor: 7.446
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  8 in total

1.  Structural investigation of 2-naphthyl phenyl ether inhibitors bound to WT and Y181C reverse transcriptase highlights key features of the NNRTI binding site.

Authors:  Vincent N Duong; Joseph A Ippolito; Albert H Chan; Won-Gil Lee; Krasimir A Spasov; William L Jorgensen; Karen S Anderson
Journal:  Protein Sci       Date:  2020-08-05       Impact factor: 6.725

2.  Covalent inhibitors for eradication of drug-resistant HIV-1 reverse transcriptase: From design to protein crystallography.

Authors:  Albert H Chan; Won-Gil Lee; Krasimir A Spasov; José A Cisneros; Shalley N Kudalkar; Zaritza O Petrova; Amanda B Buckingham; Karen S Anderson; William L Jorgensen
Journal:  Proc Natl Acad Sci U S A       Date:  2017-08-21       Impact factor: 11.205

Review 3.  Evolving understanding of HIV-1 reverse transcriptase structure, function, inhibition, and resistance.

Authors:  Francesc Xavier Ruiz; Eddy Arnold
Journal:  Curr Opin Struct Biol       Date:  2020-01-11       Impact factor: 6.809

4.  Structural and pharmacological evaluation of a novel non-nucleoside reverse transcriptase inhibitor as a promising long acting nanoformulation for treating HIV.

Authors:  Shalley N Kudalkar; Irfan Ullah; Nicole Bertoletti; Hanna K Mandl; José A Cisneros; Jagadish Beloor; Albert H Chan; Elias Quijano; W Mark Saltzman; William L Jorgensen; Priti Kumar; Karen S Anderson
Journal:  Antiviral Res       Date:  2019-04-26       Impact factor: 5.970

5.  Systematic Study of Effects of Structural Modifications on the Aqueous Solubility of Drug-like Molecules.

Authors:  José A Cisneros; Michael J Robertson; Brandon Q Mercado; William L Jorgensen
Journal:  ACS Med Chem Lett       Date:  2016-12-01       Impact factor: 4.345

Review 6.  Nitrile-containing pharmaceuticals: target, mechanism of action, and their SAR studies.

Authors:  Xi Wang; Yuanxun Wang; Xuemin Li; Zhenyang Yu; Chun Song; Yunfei Du
Journal:  RSC Med Chem       Date:  2021-08-10

7.  Covalent Inhibition of Wild-Type HIV-1 Reverse Transcriptase Using a Fluorosulfate Warhead.

Authors:  Joseph A Ippolito; Haichan Niu; Nicole Bertoletti; Zachary J Carter; Shengyan Jin; Krasimir A Spasov; José A Cisneros; Margarita Valhondo; Kara J Cutrona; Karen S Anderson; William L Jorgensen
Journal:  ACS Med Chem Lett       Date:  2021-01-06       Impact factor: 4.345

Review 8.  Avoiding Drug Resistance in HIV Reverse Transcriptase.

Authors:  Maria E Cilento; Karen A Kirby; Stefan G Sarafianos
Journal:  Chem Rev       Date:  2021-01-28       Impact factor: 60.622
  8 in total

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