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Title: Design of substituted tetrahydrofuran derivatives for HIV-1 protease inhibitors: synthesis, biological evaluation, and X-ray structural studies

Journal Article · · Organic and Biomolecular Chemistry
DOI: https://doi.org/10.1039/D4OB00506F · OSTI ID:2395971
ORCiD logo [1];  [2];  [2];  [2];  [2];  [3];  [3]; ORCiD logo [4];  [5];  [3];  [6]
  1. Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907, USA, Department of Medicinal Chemistry and Molecular Pharmacology, Purdue University, 560 Oval Drive, West Lafayette, IN 47907, USA
  2. Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907, USA
  3. Department of Biology, Georgia State University, Atlanta, Georgia 30303, USA
  4. Departments of Infectious Diseases and Hematology, Kumamoto University Graduate School of Biomedical Sciences, Kumamoto 860-8556, Japan
  5. Center for Clinical Sciences, National Center for Global Health and Medicine, Tokyo 162-8655, Japan
  6. Departments of Infectious Diseases and Hematology, Kumamoto University Graduate School of Biomedical Sciences, Kumamoto 860-8556, Japan, Center for Clinical Sciences, National Center for Global Health and Medicine, Tokyo 162-8655, Japan, Experimental Retrovirology Section, HIV and AIDS Malignancy Branch, National Cancer Institute, National Institutes of Health, Bethesda, MD 20892, USA
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A series of potent HIV-1 protease inhibitors with novel P2-ligands have been designed, synthesized and evaluated.

Sponsoring Organization:
USDOE
Grant/Contract Number:
W-31109-ENG-38
OSTI ID:
2395971
Journal Information:
Organic and Biomolecular Chemistry, Journal Name: Organic and Biomolecular Chemistry Journal Issue: 36 Vol. 22; ISSN OBCRAK; ISSN 1477-0520
Publisher:
Royal Society of Chemistry (RSC)Copyright Statement
Country of Publication:
United Kingdom
Language:
English

References (45)

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Ultra-high Resolution Crystal Structure of HIV-1 Protease Mutant Reveals Two Binding Sites for Clinical Inhibitor TMC114 journal October 2006
Design of HIV Protease Inhibitors Targeting Protein Backbone: An Effective Strategy for Combating Drug Resistance journal January 2008
Highly Drug-Resistant HIV-1 Protease Mutant PRS17 Shows Enhanced Binding to Substrate Analogues journal May 2019
Darunavir, a conceptually new HIV-1 protease inhibitor for the treatment of drug-resistant HIV journal December 2007
Current status and challenges of antiretroviral research and therapy journal January 2010
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Novel bis-Tetrahydrofuranylurethane-Containing Nonpeptidic Protease Inhibitor (PI) UIC-94017 (TMC114) with Potent Activity against Multi-PI-Resistant Human Immunodeficiency Virus In Vitro journal September 2003
Amprenavir complexes with HIV-1 protease and its drug-resistant mutants altering hydrophobic clusters: HIV protease mutants altering hydrophobic clusters journal August 2010
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Potent HIV‐1 Protease Inhibitors Containing Carboxylic and Boronic Acids: Effect on Enzyme Inhibition and Antiviral Activity and Protein‐Ligand X‐ray Structural Studies journal October 2019
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In Vitro Selection of Highly Darunavir-Resistant and Replication-Competent HIV-1 Variants by Using a Mixture of Clinical HIV-1 Isolates Resistant to Multiple Conventional Protease Inhibitors journal September 2010
Design and Synthesis of Potent HIV-1 Protease Inhibitors Incorporating Hexahydrofuropyranol-Derived High Affinity P 2 Ligands: Structure−Activity Studies and Biological Evaluation journal January 2011
Beyond darunavir: recent development of next generation HIV-1 protease inhibitors to combat drug resistance journal January 2022
Current and future priorities for the development of optimal HIV drugs journal March 2019
A Potent Human Immunodeficiency Virus Type 1 Protease Inhibitor, UIC-94003 (TMC-126), and Selection of a Novel (A28S) Mutation in the Protease Active Site journal February 2002
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Design of the anti-HIV protease inhibitor darunavir book January 2013
Recent Progress in the Development of HIV-1 Protease Inhibitors for the Treatment of HIV/AIDS journal January 2016

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