Literature DB >> 26185337

Enantioselective Synthesis of Dioxatriquinane Structural Motifs for HIV-1 Protease Inhibitors Using a Cascade Radical Cyclization.

Arun K Ghosh1, Chun-Xiao Xu1, Heather L Osswald1.   

Abstract

Synthesis of novel HIV-1 protease inhibitors incorporating dioxatriquinane-derived P2-ligands is described. The tricyclic ligand alcohol contains five contiguous chiral centers. The ligand alcohols were prepared in optically active form by an enzymatic asymmetrization of mesodiacetate, cascade radical cyclization, and Lewis acid catalyzed reduction as the key steps. Inhibitors with dioxatriquinane-derived P2-ligands exhibited low nanomolar HIV-1 protease activity.

Entities:  

Keywords:  Cascade; Dioxatriquinane; HIV-1 protease; Inhibitor; Radical

Year:  2015        PMID： 26185337      PMCID： PMC4500529          DOI： 10.1016/j.tetlet.2015.01.019

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  17 in total

Review 1.  Bis-tetrahydrofuran: a privileged ligand for darunavir and a new generation of hiv protease inhibitors that combat drug resistance.

Authors:  Arun K Ghosh; Perali Ramu Sridhar; Nagaswamy Kumaragurubaran; Yasuhiro Koh; Irene T Weber; Hiroaki Mitsuya
Journal:  ChemMedChem       Date:  2006-09       Impact factor: 3.466

Review 2.  Why do patients fail HIV therapy?

Authors:  L Waters; M Nelson
Journal:  Int J Clin Pract       Date:  2007-06       Impact factor: 2.503

3.  Potent HIV protease inhibitors incorporating high-affinity P2-ligands and (R)-(hydroxyethylamino)sulfonamide isostere.

Authors:  A K Ghosh; J F Kincaid; W Cho; D E Walters; K Krishnan; K A Hussain; Y Koo; H Cho; C Rudall; L Holland; J Buthod
Journal:  Bioorg Med Chem Lett       Date:  1998-03-17       Impact factor: 2.823

4.  Novel P2 tris-tetrahydrofuran group in antiviral compound 1 (GRL-0519) fills the S2 binding pocket of selected mutants of HIV-1 protease.

Authors:  Hongmei Zhang; Yuan-Fang Wang; Chen-Hsiang Shen; Johnson Agniswamy; Kalapala Venkateswara Rao; Chun-Xiao Xu; Arun K Ghosh; Robert W Harrison; Irene T Weber
Journal:  J Med Chem       Date:  2013-01-23       Impact factor: 7.446

5.  A simple, continuous fluorometric assay for HIV protease.

Authors:  M V Toth; G R Marshall
Journal:  Int J Pept Protein Res       Date:  1990-12

6.  Probing multidrug-resistance and protein-ligand interactions with oxatricyclic designed ligands in HIV-1 protease inhibitors.

Authors:  Arun K Ghosh; Chun-Xiao Xu; Kalapala Venkateswara Rao; Abigail Baldridge; Johnson Agniswamy; Yuan-Fang Wang; Irene T Weber; Manabu Aoki; Salcedo Gomez Pedro Miguel; Masayuki Amano; Hiroaki Mitsuya
Journal:  ChemMedChem       Date:  2010-11-08       Impact factor: 3.466

7.  Novel bis-tetrahydrofuranylurethane-containing nonpeptidic protease inhibitor (PI) UIC-94017 (TMC114) with potent activity against multi-PI-resistant human immunodeficiency virus in vitro.

Authors:  Yasuhiro Koh; Hirotomo Nakata; Kenji Maeda; Hiromi Ogata; Geoffrey Bilcer; Thippeswamy Devasamudram; John F Kincaid; Peter Boross; Yuan-Fang Wang; Yunfeng Tie; Patra Volarath; Laquasha Gaddis; Robert W Harrison; Irene T Weber; Arun K Ghosh; Hiroaki Mitsuya
Journal:  Antimicrob Agents Chemother       Date:  2003-10       Impact factor: 5.191

Review 8.  Design of HIV protease inhibitors targeting protein backbone: an effective strategy for combating drug resistance.

Authors:  Arun K Ghosh; Bruno D Chapsal; Irene T Weber; Hiroaki Mitsuya
Journal:  Acc Chem Res       Date:  2007-08-28       Impact factor: 22.384

Review 9.  Darunavir, a conceptually new HIV-1 protease inhibitor for the treatment of drug-resistant HIV.

Authors:  Arun K Ghosh; Zachary L Dawson; Hiroaki Mitsuya
Journal:  Bioorg Med Chem       Date:  2007-09-14       Impact factor: 3.641

Review 10.  Enhancing protein backbone binding--a fruitful concept for combating drug-resistant HIV.

Authors:  Arun K Ghosh; David D Anderson; Irene T Weber; Hiroaki Mitsuya
Journal:  Angew Chem Int Ed Engl       Date:  2012-01-31       Impact factor: 15.336
View more
  4 in total

Review 1.  Recent Progress in the Development of HIV-1 Protease Inhibitors for the Treatment of HIV/AIDS.

Authors:  Arun K Ghosh; Heather L Osswald; Gary Prato
Journal:  J Med Chem       Date:  2016-01-22       Impact factor: 7.446

2.  Nature Inspired Molecular Design: Stereoselective Synthesis of Bicyclic and Polycyclic Ethers for Potent HIV-1 Protease Inhibitors.

Authors:  Arun K Ghosh; Margherita Brindisi
Journal:  Asian J Org Chem       Date:  2018-06-08       Impact factor: 3.319

3.  Photoinduced Cycloadditions in the Diversity-Oriented Synthesis Toolbox: Increasing Complexity with Straightforward Postphotochemical Modifications.

Authors:  Weston J Umstead; Olga A Mukhina; N N Bhuvan Kumar; Andrei G Kutateladze
Journal:  Aust J Chem       Date:  2015-07-24       Impact factor: 1.321

4.  Catalysis-Enabled Concise and Stereoselective Total Synthesis of the Tricyclic Prostaglandin D2 Metabolite Methyl Ester.

Authors:  Hunter S Sims; Pedro de Andrade Horn; Ryota Isshiki; Melissa Lim; Yan Xu; Robert H Grubbs; Mingji Dai
Journal:  Angew Chem Int Ed Engl       Date:  2021-12-14       Impact factor: 15.336
  4 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.