Literature DB >> 26166629

Discovery and crystallography of bicyclic arylaminoazines as potent inhibitors of HIV-1 reverse transcriptase.

Won-Gil Lee1, Kathleen M Frey2, Ricardo Gallardo-Macias1, Krasimir A Spasov2, Albert H Chan2, Karen S Anderson3, William L Jorgensen4.   

Abstract

Non-nucleoside inhibitors of HIV-1 reverse transcriptase (HIV-RT) are reported that incorporate a 7-indolizinylamino or 2-naphthylamino substituent on a pyrimidine or 1,3,5-triazine core. The most potent compounds show below 10 nanomolar activity towards wild-type HIV-1 and variants bearing Tyr181Cys and Lys103Asn/Tyr181Cys resistance mutations. The compounds also feature good aqueous solubility. Crystal structures for two complexes enhance the analysis of the structure-activity data.
Copyright © 2015 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Drug solubility; HIV-1 reverse transcriptase; NNRTI; Protein crystallography; Structure-based drug design

Mesh：

Substances：

Year:  2015        PMID： 26166629      PMCID： PMC4607639          DOI： 10.1016/j.bmcl.2015.06.074

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


  14 in total

1.  Study of equilibrium solubility measurement by saturation shake-flask method using hydrochlorothiazide as model compound.

Authors:  Edit Baka; John E A Comer; Krisztina Takács-Novák
Journal:  J Pharm Biomed Anal       Date:  2007-11-01       Impact factor: 3.935

Review 2.  Treatment of HIV infection with once-daily regimens.

Authors:  Nitipong Permpalung; Opass Putcharoen; Anchalee Avihingsanon; Kiat Ruxrungtham
Journal:  Expert Opin Pharmacother       Date:  2012-10-08       Impact factor: 3.889

3.  Picomolar Inhibitors of HIV-1 Reverse Transcriptase: Design and Crystallography of Naphthyl Phenyl Ethers.

Authors:  Won-Gil Lee; Kathleen M Frey; Ricardo Gallardo-Macias; Krasimir A Spasov; Mariela Bollini; Karen S Anderson; William L Jorgensen
Journal:  ACS Med Chem Lett       Date:  2014-10-13       Impact factor: 4.345

Review 4.  In search of a novel anti-HIV drug: multidisciplinary coordination in the discovery of 4-[[4-[[4-[(1E)-2-cyanoethenyl]-2,6-dimethylphenyl]amino]-2- pyrimidinyl]amino]benzonitrile (R278474, rilpivirine).

Authors:  Paul A J Janssen; Paul J Lewi; Eddy Arnold; Frits Daeyaert; Marc de Jonge; Jan Heeres; Luc Koymans; Maarten Vinkers; Jérôme Guillemont; Elisabeth Pasquier; Mike Kukla; Don Ludovici; Koen Andries; Marie-Pierre de Béthune; Rudi Pauwels; Kalyan Das; Art D Clark; Yulia Volovik Frenkel; Stephen H Hughes; Bart Medaer; Fons De Knaep; Hilde Bohets; Fred De Clerck; Ann Lampo; Peter Williams; Paul Stoffels
Journal:  J Med Chem       Date:  2005-03-24       Impact factor: 7.446

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

Review 6.  Metabolic and body composition effects of newer antiretrovirals in HIV-infected patients.

Authors:  Suman Srinivasa; Steven K Grinspoon
Journal:  Eur J Endocrinol       Date:  2014-04-10       Impact factor: 6.664

7.  Extension into the entrance channel of HIV-1 reverse transcriptase--crystallography and enhanced solubility.

Authors:  Mariela Bollini; Kathleen M Frey; José A Cisneros; Krasimir A Spasov; Kalyan Das; Joseph D Bauman; Eddy Arnold; Karen S Anderson; William L Jorgensen
Journal:  Bioorg Med Chem Lett       Date:  2013-07-08       Impact factor: 2.823

8.  Optimization of diarylazines as anti-HIV agents with dramatically enhanced solubility.

Authors:  Mariela Bollini; José A Cisneros; Krasimir A Spasov; Karen S Anderson; William L Jorgensen
Journal:  Bioorg Med Chem Lett       Date:  2013-07-08       Impact factor: 2.823

9.  An analysis of FDA-approved drugs for infectious disease: HIV/AIDS drugs.

Authors:  Michael S Kinch; Eric Patridge
Journal:  Drug Discov Today       Date:  2014-05-28       Impact factor: 8.369

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
View more
  5 in total

1.  Predicting Binding Free Energies in a Large Combinatorial Chemical Space Using Multisite λ Dynamics.

Authors:  Jonah Z Vilseck; Kira A Armacost; Ryan L Hayes; Garrett B Goh; Charles L Brooks
Journal:  J Phys Chem Lett       Date:  2018-06-06       Impact factor: 6.475

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

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

3.  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

Review 4.  The "Sticky Patch" Model of Crystallization and Modification of Proteins for Enhanced Crystallizability.

Authors:  Zygmunt S Derewenda; Adam Godzik
Journal:  Methods Mol Biol       Date:  2017

5.  Structural Studies and Structure Activity Relationships for Novel Computationally Designed Non-nucleoside Inhibitors and Their Interactions With HIV-1 Reverse Transcriptase.

Authors:  Kathleen M Frey; Nicole Bertoletti; Albert H Chan; Joseph A Ippolito; Mariela Bollini; Krasimir A Spasov; William L Jorgensen; Karen S Anderson
Journal:  Front Mol Biosci       Date:  2022-02-14
  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.