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

PubWeight™: 0.78‹?›

🔗 View Article (PMC 3179850)

Published in Bioorg Med Chem Lett on December 05, 2009

Authors

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

Author Affiliations

1: Departments of Chemistry and Medicinal Chemistry, Purdue University, West Lafayette, IN 47907, United States. akghosh@purdue.edu

Articles cited by this

Active human immunodeficiency virus protease is required for viral infectivity. Proc Natl Acad Sci U S A (1988) 10.77

Public health implications of antiretroviral therapy and HIV drug resistance. JAMA (1998) 4.72

AIDS--the first 20 years. N Engl J Med (2001) 3.26

Novel bis-tetrahydrofuranylurethane-containing nonpeptidic protease inhibitor (PI) UIC-94017 (TMC114) with potent activity against multi-PI-resistant human immunodeficiency virus in vitro. Antimicrob Agents Chemother (2003) 3.23

Design of HIV protease inhibitors targeting protein backbone: an effective strategy for combating drug resistance. Acc Chem Res (2007) 2.16

Factors associated with clinical and virological failure in patients receiving a triple therapy including a protease inhibitor. AIDS (2000) 2.14

A simple, continuous fluorometric assay for HIV protease. Int J Pept Protein Res (1990) 2.07

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. J Virol (2002) 2.02

Structure-based design of novel HIV-1 protease inhibitors to combat drug resistance. J Med Chem (2006) 1.75

Potent HIV protease inhibitors incorporating high-affinity P2-ligands and (R)-(hydroxyethylamino)sulfonamide isostere. Bioorg Med Chem Lett (1998) 1.75

JE-2147: a dipeptide protease inhibitor (PI) that potently inhibits multi-PI-resistant HIV-1. Proc Natl Acad Sci U S A (1999) 1.65

Bis-tetrahydrofuran: a privileged ligand for darunavir and a new generation of hiv protease inhibitors that combat drug resistance. ChemMedChem (2006) 1.40

The impact of transmitted drug resistance on the natural history of HIV infection and response to first-line therapy. AIDS (2006) 1.37

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). J Org Chem (2004) 1.32

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. Antimicrob Agents Chemother (2008) 1.05

A structural and thermodynamic escape mechanism from a drug resistant mutation of the HIV-1 protease. Proteins (2004) 1.02

Flexible cyclic ethers/polyethers as novel P2-ligands for HIV-1 protease inhibitors: design, synthesis, biological evaluation, and protein-ligand X-ray studies. J Med Chem (2008) 1.02

Antiviral activity of UIC-PI, a novel inhibitor of the human immunodeficiency virus type 1 protease. Antiviral Res (2002) 0.98

Structural evidence for effectiveness of darunavir and two related antiviral inhibitors against HIV-2 protease. J Mol Biol (2008) 0.95

Potent HIV protease inhibitors: the development of tetrahydrofuranylglycines as novel P2-ligands and pyrazine amides as P3-ligands. J Med Chem (1993) 0.93

Potent HIV-1 protease inhibitors incorporating meso-bicyclic urethanes as P2-ligands: structure-based design, synthesis, biological evaluation and protein-ligand X-ray studies. Org Biomol Chem (2008) 0.85

Asymmetric nitroaldol reaction. Synthesis of taxotere side chain and (-)-bestatin using (1R)-8-phenylmenthyl glyoxylate. J Org Chem (2004) 0.83

Design and synthesis of new orally active inhibitors of human neutrophil elastase. Bioorg Med Chem (2001) 0.80

Structure-activity and structure-metabolism relationships of HIV protease inhibitors containing the 3-hydroxy-2-methylbenzoyl-allophenylnorstatine structure. Bioorg Med Chem (2004) 0.79

Articles by these authors

Novel bis-tetrahydrofuranylurethane-containing nonpeptidic protease inhibitor (PI) UIC-94017 (TMC114) with potent activity against multi-PI-resistant human immunodeficiency virus in vitro. Antimicrob Agents Chemother (2003) 3.23

Highly effective treatment of acquired immunodeficiency syndrome-related lymphoma with dose-adjusted EPOCH: impact of antiretroviral therapy suspension and tumor biology. Blood (2003) 2.46

Design of HIV protease inhibitors targeting protein backbone: an effective strategy for combating drug resistance. Acc Chem Res (2007) 2.16

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. J Virol (2002) 2.02

Increased malignancy of Neu-induced mammary tumors overexpressing active transforming growth factor beta1. Mol Cell Biol (2003) 1.99

Effect of SLCO1B3 haplotype on testosterone transport and clinical outcome in caucasian patients with androgen-independent prostatic cancer. Clin Cancer Res (2008) 1.95

Spirodiketopiperazine-based CCR5 inhibitor which preserves CC-chemokine/CCR5 interactions and exerts potent activity against R5 human immunodeficiency virus type 1 in vitro. J Virol (2004) 1.92

Amino acid substitutions in Gag protein at non-cleavage sites are indispensable for the development of a high multitude of HIV-1 resistance against protease inhibitors. J Biol Chem (2001) 1.91

Conditional overexpression of active transforming growth factor beta1 in vivo accelerates metastases of transgenic mammary tumors. Cancer Res (2004) 1.84

Potent inhibition of HIV-1 replication by novel non-peptidyl small molecule inhibitors of protease dimerization. J Biol Chem (2007) 1.79

Structure-based design of novel HIV-1 protease inhibitors to combat drug resistance. J Med Chem (2006) 1.75

beta-Secretase as a therapeutic target for Alzheimer's disease. Neurotherapeutics (2008) 1.74

Overexpression of HER2 (erbB2) in human breast epithelial cells unmasks transforming growth factor beta-induced cell motility. J Biol Chem (2004) 1.72

Multimode, cooperative mechanism of action of allosteric HIV-1 integrase inhibitors. J Biol Chem (2012) 1.55

Structural and molecular interactions of CCR5 inhibitors with CCR5. J Biol Chem (2006) 1.55

Darunavir, a conceptually new HIV-1 protease inhibitor for the treatment of drug-resistant HIV. Bioorg Med Chem (2007) 1.51

Allosteric integrase inhibitor potency is determined through the inhibition of HIV-1 particle maturation. Proc Natl Acad Sci U S A (2013) 1.49

Identification of aberrantly methylated genes in association with adult T-cell leukemia. Cancer Res (2004) 1.48

Properties of two cataract-associated mutations located in the NH2 terminus of connexin 46. Am J Physiol Cell Physiol (2013) 1.46

Mechanism of inhibition of HIV-1 reverse transcriptase by 4'-Ethynyl-2-fluoro-2'-deoxyadenosine triphosphate, a translocation-defective reverse transcriptase inhibitor. J Biol Chem (2009) 1.45

Activity against human immunodeficiency virus type 1, intracellular metabolism, and effects on human DNA polymerases of 4'-ethynyl-2-fluoro-2'-deoxyadenosine. Antimicrob Agents Chemother (2007) 1.43

Bis-tetrahydrofuran: a privileged ligand for darunavir and a new generation of hiv protease inhibitors that combat drug resistance. ChemMedChem (2006) 1.40

Altered HIV-1 Gag protein interactions with cyclophilin A (CypA) on the acquisition of H219Q and H219P substitutions in the CypA binding loop. J Biol Chem (2005) 1.38

Conformational changes in BAK, a pore-forming proapoptotic Bcl-2 family member, upon membrane insertion and direct evidence for the existence of BH3-BH3 contact interface in BAK homo-oligomers. J Biol Chem (2010) 1.36

2'-deoxy-4'-C-ethynyl-2-halo-adenosines active against drug-resistant human immunodeficiency virus type 1 variants. Int J Biochem Cell Biol (2008) 1.36

A novel bis-tetrahydrofuranylurethane-containing nonpeptidic protease inhibitor (PI), GRL-98065, is potent against multiple-PI-resistant human immunodeficiency virus in vitro. Antimicrob Agents Chemother (2007) 1.34

Characterization of monocyte/macrophage subsets in the skin and peripheral blood derived from patients with systemic sclerosis. Arthritis Res Ther (2010) 1.33

Prognostic impact of circulating tumor cells in patients with small cell lung cancer. J Thorac Oncol (2012) 1.29

Potent anti-R5 human immunodeficiency virus type 1 effects of a CCR5 antagonist, AK602/ONO4128/GW873140, in a novel human peripheral blood mononuclear cell nonobese diabetic-SCID, interleukin-2 receptor gamma-chain-knocked-out AIDS mouse model. J Virol (2005) 1.29

Biologic correlation of 2-[18F]-fluoro-2-deoxy-D-glucose uptake on positron emission tomography in thymic epithelial tumors. J Clin Oncol (2010) 1.27

Synthesis and pharmacological evaluation of potent and highly selective D3 receptor ligands: inhibition of cocaine-seeking behavior and the role of dopamine D3/D2 receptors. J Med Chem (2003) 1.24

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. J Virol (2010) 1.24

(Z)- and (E)-[2-Fluoro-2-(hydroxymethyl)cyclopropylidene]methylpurines and -pyrimidines, a new class of methylenecyclopropane analogues of nucleosides: synthesis and antiviral activity. J Med Chem (2004) 1.19

Specific targeting of hepatitis C virus NS3 RNA helicase. Discovery of the potent and selective competitive nucleotide-mimicking inhibitor QU663. Biochemistry (2005) 1.17

Down-regulation of PU.1 by methylation of distal regulatory elements and the promoter is required for myeloma cell growth. Cancer Res (2007) 1.15

The A128T resistance mutation reveals aberrant protein multimerization as the primary mechanism of action of allosteric HIV-1 integrase inhibitors. J Biol Chem (2013) 1.14

Potent activity of a nucleoside reverse transcriptase inhibitor, 4'-ethynyl-2-fluoro-2'-deoxyadenosine, against human immunodeficiency virus type 1 infection in a model using human peripheral blood mononuclear cell-transplanted NOD/SCID Janus kinase 3 knockout mice. Antimicrob Agents Chemother (2009) 1.14

A 4'-C-ethynyl-2',3'-dideoxynucleoside analogue highlights the role of the 3'-OH in anti-HIV active 4'-C-ethynyl-2'-deoxy nucleosides. J Med Chem (2004) 1.11

Probing multidrug-resistance and protein-ligand interactions with oxatricyclic designed ligands in HIV-1 protease inhibitors. ChemMedChem (2010) 1.11

The structural evolution of β-secretase inhibitors: a focus on the development of small-molecule inhibitors. Curr Top Med Chem (2013) 1.11

Oligomycin frames a common drug-binding site in the ATP synthase. Proc Natl Acad Sci U S A (2012) 1.10

Specific targeting highly conserved residues in the HIV-1 reverse transcriptase primer grip region. Design, synthesis, and biological evaluation of novel, potent, and broad spectrum NNRTIs with antiviral activity. J Med Chem (2005) 1.08

Design, synthesis, and biological evaluation of the combinatorial library with a new spirodiketopiperazine scaffold. Discovery of novel potent and selective low-molecular-weight CCR5 antagonists. J Med Chem (2006) 1.08

Enhancing protein backbone binding--a fruitful concept for combating drug-resistant HIV. Angew Chem Int Ed Engl (2012) 1.08

Decreased stimulation of CD4+ T cell proliferation and IL-2 production by highly enriched populations of HIV-infected dendritic cells. J Immunol (2003) 1.08

Design of HIV-1 protease inhibitors with pyrrolidinones and oxazolidinones as novel P1'-ligands to enhance backbone-binding interactions with protease: synthesis, biological evaluation, and protein-ligand X-ray studies. J Med Chem (2009) 1.07

Size-based isolation of circulating tumor cells in lung cancer patients using a microcavity array system. PLoS One (2013) 1.06

Spirodiketopiperazine-based CCR5 antagonists: Lead optimization from biologically active metabolite. Bioorg Med Chem Lett (2006) 1.06

Activation of the endoplasmic reticulum stress pathway is associated with survival of myeloma cells. Leuk Lymphoma (2006) 1.06

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. Antimicrob Agents Chemother (2008) 1.05

FoxP3+ regulatory T cells are distinct from leukemia cells in HTLV-1-associated adult T-cell leukemia. Int J Cancer (2009) 1.05

Overexpression of c-Maf contributes to T-cell lymphoma in both mice and human. Cancer Res (2006) 1.04

Involvement of the second extracellular loop and transmembrane residues of CCR5 in inhibitor binding and HIV-1 fusion: insights into the mechanism of allosteric inhibition. J Mol Biol (2008) 1.04

2'-deoxy-4'-C-ethynyl-2-fluoroadenosine: a nucleoside reverse transcriptase inhibitor with highly potent activity against wide spectrum of HIV-1 strains, favorable toxic profiles, and stability in plasma. Nucleosides Nucleotides Nucleic Acids (2007) 1.03

The mitochondrial citrate transport protein: probing the secondary structure of transmembrane domain III, identification of residues that likely comprise a portion of the citrate transport pathway, and development of a model for the putative TMDIII-TMDIII' interface. J Biol Chem (2003) 1.03

Macrophage inflammatory protein-1 alpha is produced by human multiple myeloma (MM) cells and its expression correlates with bone lesions in patients with MM. Br J Haematol (2003) 1.02

Flexible cyclic ethers/polyethers as novel P2-ligands for HIV-1 protease inhibitors: design, synthesis, biological evaluation, and protein-ligand X-ray studies. J Med Chem (2008) 1.02

Response rate is associated with prolonged survival in patients with advanced non-small cell lung cancer treated with gefitinib or erlotinib. J Thorac Oncol (2009) 1.02

Ion selectivity of alpha-hemolysin with beta-cyclodextrin adapter. II. Multi-ion effects studied with grand canonical Monte Carlo/Brownian dynamics simulations. J Phys Chem B (2010) 1.02

Non-cleavage site gag mutations in amprenavir-resistant human immunodeficiency virus type 1 (HIV-1) predispose HIV-1 to rapid acquisition of amprenavir resistance but delay development of resistance to other protease inhibitors. J Virol (2009) 1.01

Response of simian immunodeficiency virus to the novel nucleoside reverse transcriptase inhibitor 4'-ethynyl-2-fluoro-2'-deoxyadenosine in vitro and in vivo. Antimicrob Agents Chemother (2012) 1.01

Mechanism of hypercalcemia in adult T-cell leukemia: overexpression of receptor activator of nuclear factor kappaB ligand on adult T-cell leukemia cells. Blood (2002) 1.01

Assessment of mutational profile of Japanese lung adenocarcinoma patients by multitarget assays: a prospective, single-institute study. Cancer (2014) 1.01

Identification of the substrate binding sites within the yeast mitochondrial citrate transport protein. J Biol Chem (2007) 0.99

Design and synthesis of potent HIV-1 protease inhibitors incorporating hexahydrofuropyranol-derived high affinity P(2) ligands: structure-activity studies and biological evaluation. J Med Chem (2010) 0.98

9-{[3-fluoro-2-(hydroxymethyl)cyclopropylidene]methyl}adenines and -guanines. Synthesis and antiviral activity of all stereoisomers1. J Med Chem (2006) 0.97

Clarithromycin attenuates autophagy in myeloma cells. Int J Oncol (2010) 0.97

Immunoselection by natural killer cells of PIGA mutant cells missing stress-inducible ULBP. Blood (2005) 0.96

Synergistic interaction between the EGFR tyrosine kinase inhibitor gefitinib ("Iressa") and the DNA topoisomerase I inhibitor CPT-11 (irinotecan) in human colorectal cancer cells. Int J Cancer (2004) 0.96

GRL-0519, a novel oxatricyclic ligand-containing nonpeptidic HIV-1 protease inhibitor (PI), potently suppresses replication of a wide spectrum of multi-PI-resistant HIV-1 variants in vitro. Antimicrob Agents Chemother (2013) 0.96

Anticancer effects of ZD6474, a VEGF receptor tyrosine kinase inhibitor, in gefitinib ("Iressa")-sensitive and resistant xenograft models. Cancer Sci (2004) 0.96

Design of HIV-1 protease inhibitors with C3-substituted hexahydrocyclopentafuranyl urethanes as P2-ligands: synthesis, biological evaluation, and protein-ligand X-ray crystal structure. J Med Chem (2011) 0.96