(5E)-5-(4-ethylbenzylidene)-2-mercapto-1,3-thiazol-4(5H)-one

Base Information

• Chemical Name: (5E)-5-(4-ethylbenzylidene)-2-mercapto-1,3-thiazol-4(5H)-one
• CAS No.: 403811-55-2
• Molecular Formula: C12H11NOS2
• Molecular Weight: 249.35200
• Hs Code.: 2934100090
• DSSTox Substance ID: DTXSID301017239
• Wikidata: Q106041338
• ChEMBL ID: CHEMBL3183888
• Mol file: 403811-55-2.mol

Synonyms:c-Myc Inhibitor;(5E)-5-(4-ethylbenzylidene)-2-mercapto-1,3-thiazol-4(5H)-one;5-(4-ethylbenzylidene)-2-sulfanylidene-1,3-thiazolidin-4-one;(5E)-5-[(4-ethylphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one;CHEMBL3183888;DTXSID301017239;HMS3653E13;BCP08097;AKOS030690544;SB19479;UPCMLD0ENAT5387305:001;NCGC00185994-02;PD056405;FT-0679472;10058F4;10058 F4

Chemical Property of (5E)-5-(4-ethylbenzylidene)-2-mercapto-1,3-thiazol-4(5H)-one

Chemical Property:

• Vapor Pressure: 3.39E-06mmHg at 25°C
• Boiling Point: 387.1oC at 760 mmHg
• Flash Point: 187.9oC
• PSA: 93.53000
• Density: 1.33g/cm3
• LogP: 2.58470
• Storage Temp.: 2-8°C
• Solubility.: DMSO: >10mg/mL
• Water Solubility.: Soluble in DMSO. Soluble in water at concentrations less than 2mg/ml
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 249.02820632
• Heavy Atom Count: 16
• Complexity: 330

Purity/Quality:

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

10058-F4 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36-43
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC1=CC=C(C=C1)C=C2C(=O)NC(=S)S2
• Description: 10058-F4 (403811-55-2) effectively disables c-Myc by inhibiting the c-Myc-Max association and function.It prevents the growth of fibroblasts in a c-Myc-dependent manner. Downregulates human telomerase reverse transcriptase and enhances chemosensitivity in human hepatocellular carcinoma cells.10058-F4 induces cell cycle arrest, apoptosis and myeloid differentiation in human acute myeloid leukemia.Inhibits the MYCN/Max interaction leading to cell cycle arrest, apoptosis and neuronal differentiation in MYCN-amplified neuroblastoma cells.
• Uses: A c-Myc inhibitor that induces apoptosis

Technology Process of (5E)-5-(4-ethylbenzylidene)-2-mercapto-1,3-thiazol-4(5H)-one

There total 1 articles about (5E)-5-(4-ethylbenzylidene)-2-mercapto-1,3-thiazol-4(5H)-one 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-thioxo-4-thiazolidinone (141-84-4) + 4-ethylbenzylaldehyde (4748-78-1) → 5-[(4-ethylphenyl)methylene]-2-thioxo-4-thiazolidinone (403811-55-2)

Guidance literature:

With potassium carbonate; In water;

DOI:10.1002/chem.202004962

Reference yield: 58.0%

5-[(4-ethylphenyl)methylene]-2-thioxo-4-thiazolidinone (403811-55-2) + 3-(diphenylphosphino)propionic acid-gold(I)chloride → C27H24AuClNO2PS2

Guidance literature:

3-(diphenylphosphino)propionic acid-gold(I)chloride; With (chloromethylene)dimethyliminium chloride; In dichloromethane; at 0 ℃; for 2h;

5-[(4-ethylphenyl)methylene]-2-thioxo-4-thiazolidinone; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃;

DOI:10.1002/chem.202004962

Reference yield: 10.0%

5-[(4-ethylphenyl)methylene]-2-thioxo-4-thiazolidinone (403811-55-2) + C14H11AuCl2N2O3 → C26H20AuCl2N3O3S2

Guidance literature:

C₁₄H₁₁AuCl₂N₂O₃; With (chloromethylene)dimethyliminium chloride; In dichloromethane; at 0 ℃; for 0.5h;

5-[(4-ethylphenyl)methylene]-2-thioxo-4-thiazolidinone; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1002/chem.202004962

upstream raw materials:

2-thioxo-4-thiazolidinone

4-ethylbenzylaldehyde

Refernces