5-(5,6-Dimethoxy-1-benzimidazolyl)-3-[[2-(trifluoromethyl)phenyl]methoxy]-2-thiophenecarboxamide

Base Information

• Chemical Name: 5-(5,6-Dimethoxy-1-benzimidazolyl)-3-[[2-(trifluoromethyl)phenyl]methoxy]-2-thiophenecarboxamide
• CAS No.: 660868-91-7
• Molecular Formula: C22H18F3N3O4S
• Molecular Weight: 477.464
• European Community (EC) Number: 636-269-1
• DSSTox Substance ID: DTXSID80431373
• Nikkaji Number: J2.670.081G
• Wikidata: Q27163216
• Pharos Ligand ID: 5WMRL8SJWA3G
• ChEMBL ID: CHEMBL514499
• Mol file: 660868-91-7.mol

Synonyms:5-(5,6-dimethoxy-1H-benzimidazol-1-yl)-3-((2-(trifluoromethyl)benzyl)oxy)thiophene-2-carboxamide;DBTBOT-carboxamide;GW843682X

Chemical Property of 5-(5,6-Dimethoxy-1-benzimidazolyl)-3-[[2-(trifluoromethyl)phenyl]methoxy]-2-thiophenecarboxamide

Chemical Property:

• Boiling Point: 609.118 °C at 760 mmHg
• PKA: 15.03±0.50(Predicted)
• Flash Point: 322.183 °C
• PSA: 116.84000
• Density: 1.455 g/cm³
• LogP: 5.50120
• Storage Temp.: 2-8°C
• Solubility.: DMSO: >10mg/mL
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 7
• Exact Mass: 477.09701172
• Heavy Atom Count: 33
• Complexity: 688

Purity/Quality:

99%, ^*data from raw suppliers

GW-843682X ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=C(C=C2C(=C1)N=CN2C3=CC(=C(S3)C(=O)N)OCC4=CC=CC=C4C(F)(F)F)OC
• Description: GW843682X is a reversible, cell-permeable polo-like kinase (PLK) inhibitor. It selectively inhibits Plk1 and Plk3 (IC50s = 2.2 and 9.1 nM, respectively) over PDGFR1β, VEGFR2, Aurora A, and Cdk2/cyclin A (IC50s = 160, 360, 4,800, and 7,600 nM, respectively), as well as over 30 other kinases, in a cell-free assay. GW843682X also inhibits Plk1 activity in vitro in HeLa cells (IC50 = 0.14 μM in a reporter assay using chimeric Plk1). It inhibits growth in nine cancer cell lines in a panel (IC50s = 0.11-0.7 μM) but not of PC3 human prostate cancer cells (IC50 = 6.82 μM) or non-cancerous human diploid fibroblasts (HDFs; IC50 = 6.14 μM). GW843682X inhibits growth of MES-SA human uterine sarcoma cells, as well as of the drug-resistant, P-glycoprotein-expressing MES-SA/Dx5 subline (IC50s = 0.21 and 0.21 μM, respectively). It also inhibits the growth of patient-derived leukemia cells (IC50s = <0.25-0.8 μM). GW843682X induces G2/M cell cycle arrest and apoptosis of H460 human lung and PALL-2 and MOLM13 human leukemia cancer cells in a concentration-dependent manner.
• Uses: GW843682X is a polo-like kinase-1 (PLK1) and polo-like kinase-3 (PLK3) inhibitor.

Technology Process of 5-(5,6-Dimethoxy-1-benzimidazolyl)-3-[[2-(trifluoromethyl)phenyl]methoxy]-2-thiophenecarboxamide

There total 2 articles about 5-(5,6-Dimethoxy-1-benzimidazolyl)-3-[[2-(trifluoromethyl)phenyl]methoxy]-2-thiophenecarboxamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 34.0%

→ 5-(5,6-dimethoxy-1H-benzimidazol-1-yl)-3-[[2-(trifluoromethyl)phenyl]methoxy]-2-thiophenecarboxamide (660868-91-7)

Guidance literature:

Reference yield:

methyl 5-(5,6-dimethoxy-1H-benzimidazol-1-yl)-3-[(2-trifluoromethylbenzyl)oxy]thiophene-2-carboxylate → 5-(5,6-dimethoxy-1H-benzimidazol-1-yl)-3-[[2-(trifluoromethyl)phenyl]methoxy]-2-thiophenecarboxamide (660868-91-7)

Guidance literature:

With ammonia; In methanol; at 80 ℃; sealed tube;

DOI:10.1016/j.bmcl.2008.11.041

Reference yield: 48.0%

5-(5,6-dimethoxy-1H-benzimidazol-1-yl)-3-[[2-(trifluoromethyl)phenyl]methoxy]-2-thiophenecarboxamide (660868-91-7) → 5-(5,6-dimethoxy-1H-benzimidazol-1-yl)-3-{[2-(trifluoromethyl)benzyl]oxy}thiophene-2-carbothioamide

Guidance literature:

With Lawessons reagent; In 1,4-dioxane; at 80 ℃; for 5h;

Downstream raw materials:

5-[5,6-bis(methyloxy)-1H-benzimidazol-1-yl]-3-({[2-(trifluoromethyl)phenyl]methyl}oxy)-2-thiophenecarbonitrile

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