Literature DB >> 20034787

Synthesis and biological evaluation of novel allophenylnorstatine-based HIV-1 protease inhibitors incorporating high affinity P2-ligands.

Arun K Ghosh1, Sandra Gemma, Elena Simoni, Abigail Baldridge, D Eric Walters, Kazuhiko Ide, Yasushi Tojo, Yasuhiro Koh, Masayuki Amano, Hiroaki Mitsuya.   

Abstract

A series of stereochemically defined cyclic ethers as P2-ligands were incorporated in an allophenylnorstatine-based isostere to provide a new series of HIV-1 protease inhibitors. Inhibitors 3b and 3c, containing conformationally constrained cyclic ethers, displayed impressive enzymatic and antiviral properties and represent promising lead compounds for further optimization. Copyright (c) 2009 Elsevier Ltd. All rights reserved.

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Year:  2009        PMID： 20034787      PMCID： PMC3179850          DOI： 10.1016/j.bmcl.2009.11.123

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


  24 in total

1.  Factors associated with clinical and virological failure in patients receiving a triple therapy including a protease inhibitor.

Authors:  S Grabar; C Pradier; E Le Corfec; R Lancar; C Allavena; M Bentata; P Berlureau; C Dupont; P Fabbro-Peray; I Poizot-Martin; D Costagliola
Journal:  AIDS       Date:  2000-01-28       Impact factor: 4.177

2.  Design and synthesis of new orally active inhibitors of human neutrophil elastase.

Authors:  K Ohmoto; M Okuma; T Yamamoto; H Kijima; T Sekioka; K Kitagawa; S Yamamoto; K Tanaka; K Kawabata; A Sakata; H Imawaka; H Nakai; M Toda
Journal:  Bioorg Med Chem       Date:  2001-05       Impact factor: 3.641

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.  Structure-based design of novel HIV-1 protease inhibitors to combat drug resistance.

Authors:  Arun K Ghosh; Perali Ramu Sridhar; Sofiya Leshchenko; Azhar K Hussain; Jianfeng Li; Andrey Yu Kovalevsky; D Eric Walters; Joseph E Wedekind; Valerie Grum-Tokars; Debananda Das; Yasuhiro Koh; Kenji Maeda; Hiroyuki Gatanaga; Irene T Weber; Hiroaki Mitsuya
Journal:  J Med Chem       Date:  2006-08-24       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.  Stereoselective photochemical 1,3-dioxolane addition to 5-alkoxymethyl-2(5H)-furanone: synthesis of bis-tetrahydrofuranyl ligand for HIV protease inhibitor UIC-94017 (TMC-114).

Authors:  Arun K Ghosh; Sofiya Leshchenko; Marcus Noetzel
Journal:  J Org Chem       Date:  2004-11-12       Impact factor: 4.354

7.  GRL-02031, a novel nonpeptidic protease inhibitor (PI) containing a stereochemically defined fused cyclopentanyltetrahydrofuran potent against multi-PI-resistant human immunodeficiency virus type 1 in vitro.

Authors:  Yasuhiro Koh; Debananda Das; Sofiya Leschenko; Hirotomo Nakata; Hiromi Ogata-Aoki; Masayuki Amano; Maki Nakayama; Arun K Ghosh; Hiroaki Mitsuya
Journal:  Antimicrob Agents Chemother       Date:  2008-10-27       Impact factor: 5.191

8.  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

9.  Potent HIV-1 protease inhibitors incorporating meso-bicyclic urethanes as P2-ligands: structure-based design, synthesis, biological evaluation and protein-ligand X-ray studies.

Authors:  Arun K Ghosh; Sandra Gemma; Jun Takayama; Abigail Baldridge; Sofiya Leshchenko-Yashchuk; Heather B Miller; Yuan-Fang Wang; Andrey Y Kovalevsky; Yashiro Koh; Irene T Weber; Hiroaki Mitsuya
Journal:  Org Biomol Chem       Date:  2008-08-11       Impact factor: 3.876

10.  Structural evidence for effectiveness of darunavir and two related antiviral inhibitors against HIV-2 protease.

Authors:  Andrey Y Kovalevsky; John M Louis; Annie Aniana; Arun K Ghosh; Irene T Weber
Journal:  J Mol Biol       Date:  2008-09-20       Impact factor: 5.469
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  5 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.  Novel HIV-1 protease inhibitors (PIs) containing a bicyclic P2 functional moiety, tetrahydropyrano-tetrahydrofuran, that are potent against multi-PI-resistant HIV-1 variants.

Authors:  Kazuhiko Ide; Manabu Aoki; Masayuki Amano; Yasuhiro Koh; Ravikiran S Yedidi; Debananda Das; Sofiya Leschenko; Bruno Chapsal; Arun K Ghosh; Hiroaki Mitsuya
Journal:  Antimicrob Agents Chemother       Date:  2011-01-31       Impact factor: 5.191

Review 3.  Tetrahydrofuran, tetrahydropyran, triazoles and related heterocyclic derivatives as HIV protease inhibitors.

Authors:  Arun K Ghosh; David D Anderson
Journal:  Future Med Chem       Date:  2011-07       Impact factor: 3.808

Review 4.  Organic carbamates in drug design and medicinal chemistry.

Authors:  Arun K Ghosh; Margherita Brindisi
Journal:  J Med Chem       Date:  2015-01-07       Impact factor: 7.446

Review 5.  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
  5 in total

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