4-({5-Amino-1-[(2,6-Difluorophenyl)carbonyl]-1h-1,2,4-Triazol-3-Yl}amino)benzenesulfonamide

Base Information

• Chemical Name: 4-({5-Amino-1-[(2,6-Difluorophenyl)carbonyl]-1h-1,2,4-Triazol-3-Yl}amino)benzenesulfonamide
• CAS No.: 443797-96-4
• Molecular Formula: C15H12F2N6O3S
• Molecular Weight: 394.361
• Hs Code.: 2935009090
• UNII: 74GK72DON8
• DSSTox Substance ID: DTXSID40416207
• Nikkaji Number: J2.856.873H
• Wikidata: Q27074622
• Pharos Ligand ID: Z5BYJ1V31PDX
• ChEMBL ID: CHEMBL191003
• Mol file: 443797-96-4.mol

Synonyms:JNJ-7706621

Chemical Property of 4-({5-Amino-1-[(2,6-Difluorophenyl)carbonyl]-1h-1,2,4-Triazol-3-Yl}amino)benzenesulfonamide

Chemical Property:

• Melting Point: 149-155 °C
• Boiling Point: 676.6 °C at 760 mmHg
• PKA: 9.80±0.12(Predicted)
• Flash Point: 363 °C
• PSA: 154.37000
• Density: 1.71 g/cm³
• LogP: 3.65330
• Storage Temp.: +2C to +8C
• Sensitive.: Light Sensitive
• Solubility.: Soluble in DMSO at 15mg/ml
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 4
• Exact Mass: 394.06596576
• Heavy Atom Count: 27
• Complexity: 630

Purity/Quality:

98.0%Min ^*data from raw suppliers

JNJ-7706621 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=C(C(=C1)F)C(=O)N2C(=NC(=N2)NC3=CC=C(C=C3)S(=O)(=O)N)N)F
• Description: JNJ-7706621 is a dual inhibitor of cyclin-dependent kinases (CDKs) and Aurora kinases. It potently inhibits Cdk1/cyclin B, Cdk2/cyclin A, Cdk2/cyclin E, Cdk3/cyclin E, Cdk4/cyclin D1, Cdk6/cyclin D1, Aurora A, and Aurora B in vitro (IC50s = 9, 4, 3, 58, 253, 175, 11, and 15 nM, respectively). It shows selectivity for these enzymes over a panel of other receptors and kinases, although it exhibits submicromolar inhibition of VEGF and FGF receptors, as well as GSK3β. JNJ-7706621 blocks the growth of a large variety of cancer cell lines (IC50 values range from 112 to 514 nM), with lower potency against normal cells (IC50 values between 3.67 and 5.42 μM). It induces the regression of A375 melanoma human tumor xenografts in mice. JNJ-7706621 is a substrate for the ATP-binding cassette transporter G2, also known as breast cancer resistance protein.
• Uses: JNJ-770662 is a broad spectrum inhibitor of cyclin-dependent kinases and aurora kinases including CDK1/Cyclin B, CDK2/Cyclin A, CDK2/Cyclin E, Aurora-A and Aurora-B. JNJ-770662 has been shown to induce growth suppression and mitotic defects, these results suggest that JNJ-7706621 could be useful for cell cycle analysis and therapy of various cancers, including Ewing''s sarcoma.

Technology Process of 4-({5-Amino-1-[(2,6-Difluorophenyl)carbonyl]-1h-1,2,4-Triazol-3-Yl}amino)benzenesulfonamide

There total 8 articles about 4-({5-Amino-1-[(2,6-Difluorophenyl)carbonyl]-1h-1,2,4-Triazol-3-Yl}amino)benzenesulfonamide 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:

2,6-difluorobenzoic hydrazide (172935-91-0) + N-cyanodiphenylcarbonimidate (79463-77-7) + sulfanilamide (63-74-1) → 4-[[5-amino-1-(2,6-difluorobenzoyl)-1H-1,2,4-triazol-3-yl]amino]benzenesulfonamide (443797-96-4)

Guidance literature:

N-cyanodiphenylcarbonimidate; sulfanilamide; With pyridine; at 20 - 30 ℃; for 10h;

2,6-difluorobenzoic hydrazide; at 70 - 80 ℃; for 4h;

With ammonium chloride; In water; at 55 - 60 ℃;

Reference yield:

2,6-difluorobenzoic hydrazide (172935-91-0) + N-[4-(aminosulfonyl)phenyl]-N'-cyanocarbamidic acid phenyl ester (700805-72-7) → 4-[[5-amino-1-(2,6-difluorobenzoyl)-1H-1,2,4-triazol-3-yl]amino]benzenesulfonamide (443797-96-4)

Guidance literature:

2,6-difluorobenzoic hydrazide; N-[4-(aminosulfonyl)phenyl]-N'-cyanocarbamidic acid phenyl ester; In DMF (N,N-dimethyl-formamide); at 20 - 110 ℃; for 3.5h;

With water; In DMF (N,N-dimethyl-formamide); Product distribution / selectivity;

Reference yield:

4-((5-amino-1H-1,2,4-triazol-3-yl)amino)benzenesulfonamide (443799-31-3) + 2,6-difluorobenzoylchloride (18063-02-0) → 4-[[5-amino-1-(2,6-difluorobenzoyl)-1H-1,2,4-triazol-3-yl]amino]benzenesulfonamide (443797-96-4)

Guidance literature:

With pyridine; at 20 ℃; for 6h;

DOI:10.1021/jm050267e

upstream raw materials:

4-((5-amino-1H-1,2,4-triazol-3-yl)amino)benzenesulfonamide

2,6-difluorobenzoylchloride

phenyl-N'-cyano-N-(4-sulfamoylphenyl)carbamimidate

4-{3-[(3,5-dimethyl-pyrazol-1-yl)-imino-methyl]-thioureido}-benzenesulfonamide

Refernces

• 1、 Lin, Ronghui,Connolly, Peter J.,Huang, Shenlin,Wetter, Steven K.,Lu, Yanhua,Murray, William V.,Emanuel, Stuart L.,Gruninger, Robert H.,Fuentes-Pesquera, Angel R.,Rugg, Catherine A.,Middleton, Steven A.,Jolliffe, Linda K.. "1-Acyl-1H-[1,2,4]triazole-3,5-diamine analogues as novel and potent anticancer cyclin-dependent kinase inhibitors: Synthesis and evaluation of biological activities". . p. 4208 - 4211. Retrieved 2007/10/03.
• 2、 -. "Substituted triazole diamine derivatives as kinase inhibitors". . . Retrieved 2008/06/13.