5-[(4-Carboxyphenyl)methylene]-2-thioxo-3-[(3-trifluoromethyl)phenyl]-4-thiazolidinone

Base Information

• Chemical Name: 5-[(4-Carboxyphenyl)methylene]-2-thioxo-3-[(3-trifluoromethyl)phenyl]-4-thiazolidinone
• CAS No.: 307510-92-5
• Molecular Formula: C18H10 F3 N O3 S2
• Molecular Weight: 409.41
• European Community (EC) Number: 636-554-0
• ChEMBL ID: CHEMBL1554655
• Mol file: 307510-92-5.mol

Synonyms:3-((3-trifluoromethyl)phenyl)-5-((3-carboxyphenyl)methylene)-2-thioxo-4-thiazolidinone;CFTR(inh)-172

Chemical Property of 5-[(4-Carboxyphenyl)methylene]-2-thioxo-3-[(3-trifluoromethyl)phenyl]-4-thiazolidinone

Chemical Property:

• Vapor Pressure: 3.48E-13mmHg at 25°C
• Melting Point: 181-183 °C
• Boiling Point: 555.7ºC at 760 mmHg
• PKA: 3.88±0.10(Predicted)
• Flash Point: 289.9 ºC
• PSA: 115.00000
• Density: 1.61 g/cm³
• LogP: 4.87440
• Storage Temp.: Store at +4°C
• Solubility.: DMSO: ≥10mg/mL
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 409.00542001
• Heavy Atom Count: 27
• Complexity: 657

Purity/Quality:

98%,99%, ^*data from raw suppliers

CFTRinh 172 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,N
• Hazard Codes: Xi,N
• Statements: 36/37/38-43-50/53
• Safety Statements: 26-36/37-60-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC(=C1)N2C(=O)C(=CC3=CC=C(C=C3)C(=O)O)SC2=S)C(F)(F)F
• Isomeric SMILES: C1=CC(=CC(=C1)N2C(=O)/C(=C\C3=CC=C(C=C3)C(=O)O)/SC2=S)C(F)(F)F
• Uses: The cystic fibrosis (CF) gene encodes a cAMP-regulated chloride channel, the CF transmembrane conductance regulator (CFTR). CFTR Inhibitor-172 is a thiazolidinone that selectively blocks the CFTR channel (Ki = 300 nM) in a voltage-independent manner. It appears to directly modulate the gating of chloride at the channel and does not prevent elevation of cAMP or inhibit other pumps or channels. In mice, CFTR inhibitor-172 prevents cholera toxin-induced fluid secretion in the small intestine, when given by intraperitoneal injection. It slows cyst growth in animal models of polycystic kidney disease. As CFTR also modulates glutathione (GSH) efflux, CFTR inhibitor-172 can affect intracellular GSH concentration and reactive oxygen species balance. CFTR(inh)-172 has been used to specifically inhibit cystic fibrosis transmembrane conductance regulator (CFTR) activity. It is also used as a CFTR inhibitor Inh-172 to treat forskolin and IBMX.

Technology Process of 5-[(4-Carboxyphenyl)methylene]-2-thioxo-3-[(3-trifluoromethyl)phenyl]-4-thiazolidinone

There total 5 articles about 5-[(4-Carboxyphenyl)methylene]-2-thioxo-3-[(3-trifluoromethyl)phenyl]-4-thiazolidinone 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: 67.0%

2-thioxo-3-[3-(trifluoromethyl)phenyl]-4-thiazolidinone (315-08-2) + 4-Carboxybenzaldehyde (619-66-9) → 4-[[4-oxo-2-sulfanylidene-3-[3-(trifluoromethyl)phenyl]-1,3-thiazolidin-5-ylidene]methyl]benzoic acid (307510-92-5)

Guidance literature:

With piperidine; In ethanol; for 2h; Reflux;

DOI:10.1016/j.bmc.2008.07.044

Reference yield:

3-trifluoromethylaniline (98-16-8) → 4-[[4-oxo-2-sulfanylidene-3-[3-(trifluoromethyl)phenyl]-1,3-thiazolidin-5-ylidene]methyl]benzoic acid (307510-92-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine / ethyl acetate / Cooling with ice

2.1: sodium hydrogencarbonate / water / 2 h / pH 8 - 9

2.2: Reflux

3.1: piperidine / ethanol / 2 h / Reflux

With sodium hydrogencarbonate; triethylamine; piperidine; In ethanol; water; ethyl acetate; 3.1: Knoevenagel Condensation;

Reference yield:

1-isothiocyanato-3-trifluoromethyl-benzene (1840-19-3) → 4-[[4-oxo-2-sulfanylidene-3-[3-(trifluoromethyl)phenyl]-1,3-thiazolidin-5-ylidene]methyl]benzoic acid (307510-92-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / water; tetrahydrofuran / 3.5 h / 0 - 20 °C

1.2: Reflux

2.1: piperidine / ethanol / 2 h / Reflux

With triethylamine; piperidine; In tetrahydrofuran; ethanol; water; 2.1: Knoevenagel Condensation;

upstream raw materials:

2-thioxo-3-[3-(trifluoromethyl)phenyl]-4-thiazolidinone

4-Carboxybenzaldehyde

3-trifluoromethylaniline

1-isothiocyanato-3-trifluoromethyl-benzene

Downstream raw materials:

4-[[4-oxo-2-thioxo-3-[3-(trifluoromethyl)phenyl]-5-thiazolidinyl]methyl]benzoic acid

Refernces

• 1、 -. "WATER SOLUBLE SMALL MOLECULE INHIBITORS OF THE CYSTIC FIBROSIS TRANSMEMBRANE CONDUCTANCE REGULATOR". Page/Page column 28. . Retrieved 2011/05/08.