Literature DB >> 21806380

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

Arun K Ghosh1, David D Anderson.   

Abstract

HIV/AIDS remains a formidable disease with millions of individuals inflicted worldwide. Although treatment regimens have improved considerably, drug resistance brought on by viral mutation continues to erode their effectiveness. Intense research efforts are currently underway in search of new and improved therapies. This review is concerned with the design of novel HIV-1 protease inhibitors that incorporate heterocyclic scaffolds and which have been reported within the recent literature (2005-2010). Various examples in this review showcase the essential role heterocycles play as scaffolds and bioisosteres in HIV-1 protease inhibitor drug development. This review will hopefully stimulate the widespread application of these heterocycles in the design of other therapeutic agents.

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Year:  2011        PMID： 21806380      PMCID： PMC3164575          DOI： 10.4155/fmc.11.68

Source DB:  PubMed          Journal:  Future Med Chem        ISSN： 1756-8919            Impact factor:   3.808


  63 in total

1.  Oximinoarylsulfonamides as potent HIV protease inhibitors.

Authors:  Clinton M Yeung; Larry L Klein; Charles A Flentge; John T Randolph; Chen Zhao; MingHua Sun; Tatyana Dekhtyar; Vincent S Stoll; Dale J Kempf
Journal:  Bioorg Med Chem Lett       Date:  2005-05-02       Impact factor: 2.823

2.  Synthesis, antiviral activity, and pharmacokinetic evaluation of P3 pyridylmethyl analogs of oximinoarylsulfonyl HIV-1 protease inhibitors.

Authors:  John T Randolph; Peggy P Huang; William J Flosi; David DeGoey; Larry L Klein; Clinton M Yeung; Charles Flentge; Mingua Sun; Chen Zhao; Tatyana Dekhtyar; Hongmei Mo; Lynn Colletti; Warren Kati; Kennan C Marsh; Akhteruzzaman Molla; Dale J Kempf
Journal:  Bioorg Med Chem       Date:  2006-02-28       Impact factor: 3.641

3.  Inhibitors of HIV-1 protease by using in situ click chemistry.

Authors:  Matthew Whiting; John Muldoon; Ying-Chuan Lin; Steven M Silverman; William Lindstrom; Arthur J Olson; Hartmuth C Kolb; M G Finn; K Barry Sharpless; John H Elder; Valery V Fokin
Journal:  Angew Chem Int Ed Engl       Date:  2006-02-20       Impact factor: 15.336

4.  1,2,3-triazole as a peptide surrogate in the rapid synthesis of HIV-1 protease inhibitors.

Authors:  Ashraf Brik; Jerry Alexandratos; Ying-Chuan Lin; John H Elder; Arthur J Olson; Alexander Wlodawer; David S Goodsell; Chi-Huey Wong
Journal:  Chembiochem       Date:  2005-07       Impact factor: 3.164

5.  Potent inhibition of HIV-1 replication by novel non-peptidyl small molecule inhibitors of protease dimerization.

Authors:  Yasuhiro Koh; Shintaro Matsumi; Debananda Das; Masayuki Amano; David A Davis; Jianfeng Li; Sofiya Leschenko; Abigail Baldridge; Tatsuo Shioda; Robert Yarchoan; Arun K Ghosh; Hiroaki Mitsuya
Journal:  J Biol Chem       Date:  2007-07-17       Impact factor: 5.157

6.  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

7.  Small-sized human immunodeficiency virus type-1 protease inhibitors containing allophenylnorstatine to explore the S2' pocket.

Authors:  Koushi Hidaka; Tooru Kimura; Hamdy M Abdel-Rahman; Jeffrey-Tri Nguyen; Keith F McDaniel; William E Kohlbrenner; Akhteruzzaman Molla; Motoyasu Adachi; Taro Tamada; Ryota Kuroki; Noriko Katsuki; Yoshiaki Tanaka; Hikaru Matsumoto; Jun Wang; Yoshio Hayashi; Dale J Kempf; Yoshiaki Kiso
Journal:  J Med Chem       Date:  2009-12-10       Impact factor: 7.446

8.  A copper(I)-catalyzed 1,2,3-triazole azide-alkyne click compound is a potent inhibitor of a multidrug-resistant HIV-1 protease variant.

Authors:  Michael J Giffin; Holly Heaslet; Ashraf Brik; Ying-Chuan Lin; Gabrielle Cauvi; Chi-Huey Wong; Duncan E McRee; John H Elder; C David Stout; Bruce E Torbett
Journal:  J Med Chem       Date:  2008-09-30       Impact factor: 7.446

9.  Design and synthesis of novel HIV-1 protease inhibitors incorporating oxyindoles as the P2'-ligands.

Authors:  Arun K Ghosh; Gary Schiltz; Ramu Sridhar Perali; Sofiya Leshchenko; Stephanie Kay; D Eric Walters; Yasuhiro Koh; Kenji Maeda; Hiroaki Mitsuya
Journal:  Bioorg Med Chem Lett       Date:  2006-02-15       Impact factor: 2.823

10.  L-735,524: the design of a potent and orally bioavailable HIV protease inhibitor.

Authors:  B D Dorsey; R B Levin; S L McDaniel; J P Vacca; J P Guare; P L Darke; J A Zugay; E A Emini; W A Schleif; J C Quintero
Journal:  J Med Chem       Date:  1994-10-14       Impact factor: 7.446
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  6 in total

1.  Lewis Acid Mediated Cyclizations: Diastereoselective Synthesis of Six- to Eight-Membered Substituted Cyclic Ethers.

Authors:  Arun K Ghosh; Anthony J Tomaine; Kelsey E Cantwell
Journal:  Synthesis (Stuttg)       Date:  2017-07-25       Impact factor: 3.157

2.  Diastereoselective Synthesis of Substituted Tetrahydropyrans by Copper(II)-Bisphosphine-Catalyzed Olefin Migration and Prins Cyclization.

Authors:  Arun K Ghosh; Jorden Kass; Daniel R Nicponski; Chad Keyes
Journal:  Synthesis (Stuttg)       Date:  2012-12       Impact factor: 3.157

3.  O-Heterocycle Synthesis via Intramolecular C-H Alkoxylation Catalyzed by Iron Acetylacetonate.

Authors:  Yuyang Dong; Alexandra T Wrobel; Gerard J Porter; Jessica J Kim; Jake Z Essman; Shao-Liang Zheng; Theodore A Betley
Journal:  J Am Chem Soc       Date:  2021-05-05       Impact factor: 16.383

4.  A fission yeast cell-based system for multidrug resistant HIV-1 proteases.

Authors:  Zsigmond Benko; Dong Liang; Ge Li; Robert T Elder; Anindya Sarkar; Jun Takayama; Arun K Ghosh; Richard Y Zhao
Journal:  Cell Biosci       Date:  2017-01-11       Impact factor: 7.133

5.  Functionalisation of ethereal-based saturated heterocycles with concomitant aerobic C-H activation and C-C bond formation.

Authors:  Nehaal Ahmed; Richard J Spears; Tom D Sheppard; Vijay Chudasama
Journal:  Chem Sci       Date:  2022-06-27       Impact factor: 9.969

6.  Cu-catalyzed hydroxycyclopropanol ring-opening cyclization to tetrahydrofurans and tetrahydropyrans: short total syntheses of hyperiones.

Authors:  Weida Liang; Xinpei Cai; Mingji Dai
Journal:  Chem Sci       Date:  2020-11-20       Impact factor: 9.825
  6 in total

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