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115575-11-6 | 1H-Benzimidazole, 6-[(3-chlorophenyl)-1H-imidazol-1-ylmethyl]-
CAS No: 115575-11-6 Catalog No: AG000G7M MDL No:
Product Description
Catalog Number:
AG000G7M
Chemical Name:
1H-Benzimidazole, 6-[(3-chlorophenyl)-1H-imidazol-1-ylmethyl]-
CAS Number:
115575-11-6
Molecular Formula:
C17H13ClN4
Molecular Weight:
308.7649
IUPAC Name:
6-[(3-chlorophenyl)-imidazol-1-ylmethyl]-1H-benzimidazole
InChI:
InChI=1S/C17H13ClN4/c18-14-3-1-2-12(8-14)17(22-7-6-19-11-22)13-4-5-15-16(9-13)21-10-20-15/h1-11,17H,(H,20,21)
InChI Key:
UGFHIPBXIWJXNA-UHFFFAOYSA-N
SMILES:
Clc1cccc(c1)C(n1cncc1)c1ccc2c(c1)[nH]cn2
Properties
Complexity:
380
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
308.083g/mol
Formal Charge:
0
Heavy Atom Count:
22
Hydrogen Bond Acceptor Count:
2
Hydrogen Bond Donor Count:
1
Isotope Atom Count:
0
Molecular Weight:
308.769g/mol
Monoisotopic Mass:
308.083g/mol
Rotatable Bond Count:
3
Topological Polar Surface Area:
46.5A^2
Undefined Atom Stereocenter Count:
1
Undefined Bond Stereocenter Count:
0
XLogP3:
3.5
Literature
| Title | Journal |
|---|---|
| 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). | Journal of medicinal chemistry 20111013 |
| Small molecule inhibitors of retinoic acid 4-hydroxylase (CYP26): synthesis and biological evaluation of imidazole methyl 3-(4-(aryl-2-ylamino)phenyl)propanoates. | Journal of medicinal chemistry 20110428 |
| Pharmacophore modeling strategies for the development of novel nonsteroidal inhibitors of human aromatase (CYP19). | Bioorganic & medicinal chemistry letters 20100515 |
| Both all-trans retinoic acid and cytochrome P450 (CYP26) inhibitors affect the expression of vitamin A metabolizing enzymes and retinoid biomarkers in organotypic epidermis. | Archives of dermatological research 20090801 |
| Design and synthesis of substituted imidazole and triazole N-phenylbenzo[d]oxazolamine inhibitors of retinoic acid metabolizing enzyme CYP26. | Journal of enzyme inhibition and medicinal chemistry 20090401 |
| Effects of MAPK signaling on 1,25-dihydroxyvitamin D-mediated CYP24 gene expression in the enterocyte-like cell line, Caco-2. | Journal of cellular physiology 20090401 |
| Sequential RARbeta and alpha signalling in vivo can induce adult forebrain neural progenitor cells to differentiate into neurons through Shh and FGF signalling pathways. | Developmental biology 20090215 |
| Expression of retinoid-regulated genes in lamellar ichthyosis vs. healthy control epidermis: changes after oral treatment with liarozole. | Acta dermato-venereologica 20090101 |
| Novel azolyl-(phenylmethyl)]aryl/heteroarylamines: potent CYP26 inhibitors and enhancers of all-trans retinoic acid activity in neuroblastoma cells. | Bioorganic & medicinal chemistry 20080901 |
| [Enantiomeric separation of liarozole on amylose chiral stationary phase]. | Se pu = Chinese journal of chromatography 20080901 |
| Emerging drugs for ichthyosis. | Expert opinion on emerging drugs 20071101 |
| Oral liarozole vs. acitretin in the treatment of ichthyosis: a phase II/III multicentre, double-blind, randomized, active-controlled study. | The British journal of dermatology 20070501 |
| Effects of liarozole fumarate (R85246) in combination with tamoxifen on N-methyl-N-nitrosourea (MNU)-induced mammary carcinoma and uterus in the rat model. | BMC cancer 20070101 |
| Synthesis and CYP26A1 inhibitory activity of 1-[benzofuran-2-yl-(4-alkyl/aryl-phenyl)-methyl]-1H-triazoles. | Bioorganic & medicinal chemistry 20060601 |
| Novel tetralone-derived retinoic acid metabolism blocking agents: synthesis and in vitro evaluation with liver microsomal and MCF-7 CYP26A1 cell assays. | Journal of medicinal chemistry 20051117 |
| Potent and selective [2-imidazol-1-yl-2-(6-alkoxy-naphthalen-2-yl)-1-methyl-ethyl]-dimethyl-amines as retinoic acid metabolic blocking agents (RAMBAs). | Bioorganic & medicinal chemistry letters 20050315 |
| Inhibition of p450 17 as a new strategy for the treatment of prostate cancer. | Current medicinal chemistry 20050101 |
| Novel retinoic acid metabolism blocking agents endowed with multiple biological activities are efficient growth inhibitors of human breast and prostate cancer cells in vitro and a human breast tumor xenograft in nude mice. | Journal of medicinal chemistry 20041230 |
| Discovery of inhibitors of MCF-7 tumor cell adhesion to endothelial cells and investigation on their mode of action. | Archiv der Pharmazie 20041201 |
| Cytochrome p450 retinoic acid 4-hydroxylase inhibitors: potential agents for cancer therapy. | Mini reviews in medicinal chemistry 20020601 |
| Inhibition of all-TRANS-retinoic acid metabolism by R116010 induces antitumour activity. | British journal of cancer 20020212 |
| Liarozole markedly increases all trans-retinoic acid toxicity in mouse limb bud cell cultures: a model to explain the potency of the aromatic retinoid (E)-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylenyl)-1-propenyl] benzoic acid. | Toxicology and applied pharmacology 20020201 |
| Oral liarozole in the treatment of palmoplantar pustular psoriasis: a randomized, double-blind, placebo-controlled study. | The British journal of dermatology 20011001 |
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