Design and synthesis of substituted imidazole and triazole N-phenylbenzo[d]oxazolamine inhibitors of retinoic acid metabolizing enzyme CYP26.

PubWeight™: 0.80‹?›

🔗 View Article (PMID 18608743)

Published in J Enzyme Inhib Med Chem on April 01, 2009

Authors

Stephane Pautus1, Ahmed S Aboraia, Claire E Bassett, Andrea Brancale, Michael P Coogan, Claire Simons

Author Affiliations

1: Medicinal Chemistry, Welsh School of Pharmacy, Cardiff University, UK.

Articles by these authors

Synthesis of 5-alkylidene-1,3-dioxane-4,6-diones, an easily accessible family of axially chiral alkenes: preparation in non-racemic form and platinum binding studies. Org Biomol Chem (2006) 2.21

New arylthioindoles: potent inhibitors of tubulin polymerization. 2. Structure-activity relationships and molecular modeling studies. J Med Chem (2006) 1.28

Use of hydrogen peroxide as a biocide: new consideration of its mechanisms of biocidal action. J Antimicrob Chemother (2012) 1.24

New arylthioindoles and related bioisosteres at the sulfur bridging group. 4. Synthesis, tubulin polymerization, cell growth inhibition, and molecular modeling studies. J Med Chem (2009) 1.14

Application of d6 transition metal complexes in fluorescence cell imaging. Chem Commun (Camb) (2009) 1.14

Arylthioindoles, potent inhibitors of tubulin polymerization. J Med Chem (2004) 1.13

Synthesis and antitumor activity of 1,5-disubstituted 1,2,4-triazoles as cis-restricted combretastatin analogues. J Med Chem (2010) 1.06

Exploring the structural requirements for inhibition of the ubiquitin E3 ligase breast cancer associated protein 2 (BCA2) as a treatment for breast cancer. J Med Chem (2010) 1.06

Arylthioindole inhibitors of tubulin polymerization. 3. Biological evaluation, structure-activity relationships and molecular modeling studies. J Med Chem (2007) 1.04

Synthesis and biological evaluation of 2- and 3-aminobenzo[b]thiophene derivatives as antimitotic agents and inhibitors of tubulin polymerization. J Med Chem (2007) 1.04

Toward highly potent cancer agents by modulating the C-2 group of the arylthioindole class of tubulin polymerization inhibitors. J Med Chem (2012) 1.03

The tubulin colchicine domain: a molecular modeling perspective. ChemMedChem (2011) 1.00

Synthesis and evaluation of 1,5-disubstituted tetrazoles as rigid analogues of combretastatin A-4 with potent antiproliferative and antitumor activity. J Med Chem (2011) 0.97

Design, synthesis and evaluation of a novel double pro-drug: INX-08189. A new clinical candidate for hepatitis C virus. Bioorg Med Chem Lett (2010) 0.94

Inhibition of Vitamin D3 metabolism enhances VDR signalling in androgen-independent prostate cancer cells. J Steroid Biochem Mol Biol (2006) 0.94

Mode of action of hydrogen peroxide and other oxidizing agents: differences between liquid and gas forms. J Antimicrob Chemother (2010) 0.93

Design, synthesis, and biological evaluation of thiophene analogues of chalcones. Bioorg Med Chem (2008) 0.93

Convergent synthesis and biological evaluation of 2-amino-4-(3',4',5'-trimethoxyphenyl)-5-aryl thiazoles as microtubule targeting agents. J Med Chem (2011) 0.92

Potent CYP19 (aromatase) 1-[(benzofuran-2-yl)(phenylmethyl)pyridine, -imidazole, and -triazole inhibitors: synthesis and biological evaluation. J Med Chem (2006) 0.92

Accessible haptic technology for drug design applications. J Mol Model (2008) 0.91

The application of phosphoramidate protide technology to acyclovir confers anti-HIV inhibition. J Med Chem (2009) 0.91

Novel tetralone-derived retinoic acid metabolism blocking agents: synthesis and in vitro evaluation with liver microsomal and MCF-7 CYP26A1 cell assays. J Med Chem (2005) 0.91

Discovery of a novel HCV helicase inhibitor by a de novo drug design approach. Bioorg Med Chem Lett (2009) 0.91

Rhenium fac tricarbonyl bisimine complexes: biologically useful fluorochromes for cell imaging applications. Chem Commun (Camb) (2007) 0.89

Design and synthesis of 2-heterocyclyl-3-arylthio-1H-indoles as potent tubulin polymerization and cell growth inhibitors with improved metabolic stability. J Med Chem (2011) 0.89

Functionalisation of terpyridine complexes containing the Re(CO)3(+) moiety. Dalton Trans (2010) 0.88

New pyrrole derivatives with potent tubulin polymerization inhibiting activity as anticancer agents including hedgehog-dependent cancer. J Med Chem (2014) 0.87

Synthesis and biological evaluation of 1-methyl-2-(3',4',5'-trimethoxybenzoyl)-3-aminoindoles as a new class of antimitotic agents and tubulin inhibitors. J Med Chem (2008) 0.86

Design, synthesis and structure-activity relationship of 2-(3',4',5'-trimethoxybenzoyl)-benzo[b]furan derivatives as a novel class of inhibitors of tubulin polymerization. Bioorg Med Chem (2009) 0.86

Synthesis and biological evaluation of 2-(alkoxycarbonyl)-3-anilinobenzo[b]thiophenes and thieno[2,3-b]pyridines as new potent anticancer agents. J Med Chem (2013) 0.85

Computer-aided identification, design and synthesis of a novel series of compounds with selective antiviral activity against chikungunya virus. Antiviral Res (2013) 0.84

Synthesis and CYP24 inhibitory activity of 2-substituted-3,4-dihydro-2H-naphthalen-1-one (tetralone) derivatives. Bioorg Med Chem Lett (2004) 0.84

2-Arylamino-4-amino-5-aroylthiazoles. "One-pot" synthesis and biological evaluation of a new class of inhibitors of tubulin polymerization. J Med Chem (2009) 0.84

Synthesis and biological evaluation of 2-(3',4',5'-trimethoxybenzoyl)-3-N,N-dimethylamino benzo[b]furan derivatives as inhibitors of tubulin polymerization. Bioorg Med Chem (2008) 0.84

Design, synthesis and in vitro anticancer evaluation of 4,6-diamino-1,3,5-triazine-2-carbohydrazides and -carboxamides. Bioorg Med Chem Lett (2013) 0.83

Molecular modelling studies on Arylthioindoles as potent inhibitors of tubulin polymerization. Eur J Med Chem (2011) 0.83

Complexes in context: attempting to control the cellular uptake and localisation of rhenium fac-tricarbonyl polypyridyl complexes. Dalton Trans (2011) 0.83

Synthesis and CYP24A1 inhibitory activity of (E)-2-(2-substituted benzylidene)- and 2-(2-substituted benzyl)-6-methoxy-tetralones. Eur J Med Chem (2010) 0.83

Small molecule inhibitors of retinoic acid 4-hydroxylase (CYP26): synthesis and biological evaluation of imidazole methyl 3-(4-(aryl-2-ylamino)phenyl)propanoates. J Med Chem (2011) 0.83

Application of the phosphoramidate ProTide approach to the antiviral drug ribavirin. Bioorg Med Chem (2010) 0.82

Synthesis and biological evaluation of 3-(1H-imidazol- and triazol-1-yl)-2,2-dimethyl-3-[4-(naphthalen-2-ylamino)phenyl]propyl derivatives as small molecule inhibitors of retinoic acid 4-hydroxylase (CYP26). J Med Chem (2011) 0.82

Novel potential anticancer naphthyl phosphoramidates of BVdU: separation of diastereoisomers and assignment of the absolute configuration of the phosphorus center. J Med Chem (2006) 0.82

Homology model of human retinoic acid metabolising enzyme cytochrome P450 26A1 (CYP26A1): active site architecture and ligand binding. J Enzyme Inhib Med Chem (2006) 0.82

Specific recognition of the bicyclic pyrimidine nucleoside analogs, a new class of highly potent and selective inhibitors of varicella-zoster virus (VZV), by the VZV-encoded thymidine kinase. Mol Pharmacol (2002) 0.81

Discovery and optimization of a series of 2-aryl-4-amino-5-(3',4',5'-trimethoxybenzoyl)thiazoles as novel anticancer agents. J Med Chem (2012) 0.81

Synthesis of novel antimitotic agents based on 2-amino-3-aroyl-5-(hetero)arylethynyl thiophene derivatives. Bioorg Med Chem Lett (2010) 0.81

Small-molecule inhibitors of 25-hydroxyvitamin D-24-hydroxylase (CYP24A1): synthesis and biological evaluation. J Med Chem (2014) 0.81

Amyloid-associated nucleic acid hybridisation. PLoS One (2011) 0.81

N-methylpurine DNA glycosylase and 8-oxoguanine dna glycosylase metabolize the antiviral nucleoside 2-bromo-5,6-dichloro-1-(beta-D-ribofuranosyl)benzimidazole. Drug Metab Dispos (2006) 0.81

Importance of single molecular determinants in the fidelity of expanded genetic codes. Proc Natl Acad Sci U S A (2011) 0.81

Synthesis and CYP26A1 inhibitory activity of 1-[benzofuran-2-yl-(4-alkyl/aryl-phenyl)-methyl]-1H-triazoles. Bioorg Med Chem (2006) 0.81

Molecular dynamics at the receptor level of immunodominant myelin basic protein epitope 87-99 implicated in multiple sclerosis and its antagonists altered peptide ligands: triggering of immune response. J Mol Graph Model (2007) 0.81

Comparison of proposed putative active conformations of myelin basic protein epitope 87-99 linear altered peptide ligands by spectroscopic and modelling studies: the role of positions 91 and 96 in T-cell receptor activation. J Med Chem (2006) 0.80

Actions of Artemisia vulgaris extracts and isolated sesquiterpene lactones against receptors mediating contraction of guinea pig ileum and trachea. J Ethnopharmacol (2011) 0.80

Novel azolyl-(phenylmethyl)]aryl/heteroarylamines: potent CYP26 inhibitors and enhancers of all-trans retinoic acid activity in neuroblastoma cells. Bioorg Med Chem (2007) 0.80

Haptic-driven applications to molecular modeling: state-of-the-art and perspectives. Future Med Chem (2012) 0.79

Haptic-driven, interactive drug design: implementing a GPU-based approach to evaluate the induced fit effect. Faraday Discuss (2014) 0.79

Substituted 2-(3',4',5'-trimethoxybenzoyl)-benzo[b]thiophene derivatives as potent tubulin polymerization inhibitors. Bioorg Med Chem (2010) 0.79

Multimodal radio- (PET/SPECT) and fluorescence imaging agents based on metallo-radioisotopes: current applications and prospects for development of new agents. Dalton Trans (2011) 0.79

Homology model of 1alpha,25-dihydroxyvitamin D3 24-hydroxylase cytochrome P450 24A1 (CYP24A1): active site architecture and ligand binding. J Steroid Biochem Mol Biol (2007) 0.79

Advanced in silico approaches in antiviral research. Antivir Chem Chemother (2010) 0.79

Concise synthesis and biological evaluation of 2-Aroyl-5-amino benzo[b]thiophene derivatives as a novel class of potent antimitotic agents. J Med Chem (2013) 0.78

Identification and biological evaluation of grapefruit oil components as potential novel efflux pump modulators in methicillin-resistant Staphylococcus aureus bacterial strains. Phytochemistry (2004) 0.78

Novel imidazo[1,2-c]pyrimidine base-modified nucleosides: synthesis and antiviral evaluation. Bioorg Med Chem (2004) 0.78

Synthesis, antimitotic and antivascular activity of 1-(3',4',5'-trimethoxybenzoyl)-3-arylamino-5-amino-1,2,4-triazoles. J Med Chem (2014) 0.78

Design, synthesis, and anti-HIV activity of 2',3'-didehydro-2',3'-dideoxyuridine (d4U), 2',3'-dideoxyuridine (ddU) phosphoramidate 'ProTide' derivatives. Bioorg Med Chem Lett (2007) 0.78

One-pot synthesis and biological evaluation of 2-pyrrolidinyl-4-amino-5-(3',4',5'-trimethoxybenzoyl)thiazole: a unique, highly active antimicrotubule agent. Eur J Med Chem (2011) 0.78

Antiviral Chemistry & Chemotherapy's current antiviral agents FactFile 2006 (1st edition). Antivir Chem Chemother (2006) 0.78

GPU-accelerated molecular mechanics computations. J Comput Chem (2013) 0.77

Synthesis and CYP24A1 inhibitory activity of N-(2-(1H-imidazol-1-yl)-2-phenylethyl)arylamides. Bioorg Med Chem (2010) 0.77

Synthesis and biological evaluation of purine 2'-fluoro-2'-deoxyriboside ProTides as anti-influenza virus agents. ChemMedChem (2013) 0.77

Synthesis and antitumor molecular mechanism of agents based on amino 2-(3',4',5'-trimethoxybenzoyl)benzo[b]furan: inhibition of tubulin and induction of apoptosis. ChemMedChem (2011) 0.77

Synthesis and biological evaluation of 2-substituted-4-(3',4',5'-trimethoxyphenyl)-5-aryl thiazoles as anticancer agents. Bioorg Med Chem (2012) 0.77

Uptake and localisation of rhenium fac-tricarbonyl polypyridyls in fluorescent cell imaging experiments. Org Biomol Chem (2010) 0.77

Evaluation of a fluorescent derivative of AMD3100 and its interaction with the CXCR4 chemokine receptor. Chembiochem (2011) 0.76

Homology Modelling of Human E1 Ubiquitin Activating Enzyme. Lett Drug Des Discov (2010) 0.76

Synthesis and antimycobacterial activity of 7-O-substituted-4-methyl-2H-2-chromenone derivatives vs Mycobacterium tuberculosis. J Enzyme Inhib Med Chem (2005) 0.76

Comparative modeling of 25-hydroxycholesterol-7α-hydroxylase (CYP7B1): ligand binding and analysis of hereditary spastic paraplegia type 5 CYP7B1 mutations. J Mol Model (2011) 0.76

Indolylarylsulfones carrying a heterocyclic tail as very potent and broad spectrum HIV-1 non-nucleoside reverse transcriptase inhibitors. J Med Chem (2014) 0.76

Small molecule inhibitors of West Nile virus. Antivir Chem Chemother (2014) 0.76

The role of substrate specificity and metal binding in defining the activity and structure of an intracellular subtilisin. FEBS Open Bio (2012) 0.76

6-Azathymidine-4'-thionucleosides: synthesis and antiviral evaluation. J Enzyme Inhib Med Chem (2008) 0.76

Virtual screening-driven identification of human carbonic anhydrase inhibitors incorporating an original, new pharmacophore. Bioorg Med Chem Lett (2011) 0.76

Design of photocontrolled RNA-binding peptidomimetics. Chembiochem (2012) 0.76

Benzofuran- and furan-2-yl-(phenyl)-3-pyridylmethanols: synthesis and inhibition of P450 aromatase. J Enzyme Inhib Med Chem (2005) 0.76

Novel retinoic acid 4-hydroxylase (CYP26) inhibitors based on a 3-(1H-imidazol- and triazol-1-yl)-2,2-dimethyl-3-(4-(phenylamino)phenyl)propyl scaffold. Bioorg Med Chem (2012) 0.76