5-(4-Fluorophenyl)-2-ureidothiophene-3-carboxamide

Base Information

• Chemical Name: 5-(4-Fluorophenyl)-2-ureidothiophene-3-carboxamide
• CAS No.: 507475-17-4
• Molecular Formula: C12H10FN3O2S
• Molecular Weight: 279.294
• European Community (EC) Number: 637-136-0
• UNII: 9M632G86CC
• DSSTox Substance ID: DTXSID50432635
• Nikkaji Number: J2.819.229K
• Wikidata: Q27078038
• Pharos Ligand ID: XBS6877PWDJF
• ChEMBL ID: CHEMBL257167
• Mol file: 507475-17-4.mol

Synonyms:2-((aminocarbonyl)amino)-5-(4-fluorophenyl)-3-thiophenecarboxamide;TPCA-1;TPCA1

Chemical Property of 5-(4-Fluorophenyl)-2-ureidothiophene-3-carboxamide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 442.576°C at 760 mmHg
• PKA: 13.12±0.50(Predicted)
• Flash Point: 221.462°C
• PSA: 126.45000
• Density: 1.490
• LogP: 3.61730
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble5mg/mL, clear
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 279.04777591
• Heavy Atom Count: 19
• Complexity: 361

Purity/Quality:

99% ^*data from raw suppliers

TPCA-1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2=CC(=C(S2)NC(=O)N)C(=O)N)F
• Description: TPCA-1 (507475-17-4) selective inhibitor of IκB kinase 2 (IKK2) (IC50 = 17.9 nM).1 Inhibits production of pro-inflammatory cytokines in arthritis and other animal models of inflammation.1,2 Also attenuates NLRP3 inflammasome activation in THP-1 myeloid cells, and suppresses IL1β-induced proliferation, migration, and invasion of HeLa cells.3,4 Continuous exposure to TPCA-1 promotes expansion of hematopoietic stem/progenitor cells (HSPCs) via improved glycolysis and limited ROS production.5
• Uses: TPCA-1 is a direct dual inhibitor for both IKKβ (IKK-2) and STAT3. It inhibits STAT3 phosphorylation, DNA binding, and transactivation in vivo. Synergistic treatment of TPCA-1 with tyrosine kinase inhibitors (TKIs) can potentially be a more effective method for treating cancers.

Technology Process of 5-(4-Fluorophenyl)-2-ureidothiophene-3-carboxamide

There total 10 articles about 5-(4-Fluorophenyl)-2-ureidothiophene-3-carboxamide 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: 81.0%

methyl 5-(4-fluorophenyl)-2-ureidothiophene-3-carboxylate → 2-(carbamoylamino)-5-(4-fluorophenyl)thiophene-3-carboxamide (507475-17-4)

Guidance literature:

With trimethylaluminum; ammonium chloride; In toluene; at 0 - 60 ℃; for 12h; Inert atmosphere;

Reference yield: 63.0%

1-(3-acetyl-5-(4-fluorophenyl)thiophen-2-yl)urea → 2-(carbamoylamino)-5-(4-fluorophenyl)thiophene-3-carboxamide (507475-17-4)

Guidance literature:

With trimethylaluminum; ammonium chloride; In toluene; at 60 ℃; for 10h; Inert atmosphere;

DOI:10.1039/c8cc09595g

Reference yield: 61.0%

2-[(aminocarbonyl)amino]-5-bromo-3-thiophenecarboxamide (354812-10-5) + 2-(4-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (214360-58-4) → 2-(carbamoylamino)-5-(4-fluorophenyl)thiophene-3-carboxamide (507475-17-4)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate; In 1,4-dioxane; water; at 75 ℃; for 18h; Inert atmosphere;

DOI:10.3987/COM-19-S(F)43

upstream raw materials:

2-amino-5-(4-fluorophenyl)-3-thiophenecarboxamide

isocyanate de chlorosulfonyle

4-fluorophenylacetaldehyde

2‐(4-fluorophenyl)cyclopropane-1,1-dicarboxylic acid dimethyl ester

Refernces

• 1、 Kawasaki, Norihiko,Fukuda, Hayato,Ishihara, Jun. "Concise synthesis of tpca-1 and related thiophene-carboxamides by cross coupling". . p. 707 - 716. Retrieved 2020/01/31.
• 2、 Xie, Ming-Sheng,Zhao, Guo-Feng,Qin, Tao,Suo, Yong-Bo,Qu, Gui-Rong,Guo, Hai-Ming. "Thiourea participation in [3+2] cycloaddition with donor-acceptor cyclopropanes: A domino process to 2-amino-dihydrothiophenes". . p. 1580 - 1583. Retrieved 2019/02/07.