SH-4-54

Base Information

• Chemical Name: SH-4-54
• CAS No.: 1456632-40-8
• Molecular Formula: C29H27F5N2O5S
• Molecular Weight: 610.59
• Mol file: 1456632-40-8.mol

Synonyms:4-[[(4-cyclohexylphenyl)methyl][2-[methyl[(2,3,4,5,6-pentafluorophenyl)sulfonyl]amino]acetyl]amino]-benzoic acid;4-[[(4-cyclohexylphenyl)methyl][2-[methyl[(2,3,4,5,6-pentafluorophenyl)sulfonyl]amino]acetyl]amino]-Benzoic Acid SH-4-54

Chemical Property of SH-4-54

Chemical Property:

• Boiling Point: 717.2±70.0 °C(Predicted)
• PKA: 4.29±0.10(Predicted)
• PSA: 103.37000
• Density: 1.431±0.06 g/cm3(Predicted)
• LogP: 7.06270

Purity/Quality:

98% min ^*data from raw suppliers

4-[[(4-Cyclohexylphenyl)methyl][2-[methyl[(2,3,4,5,6-pentafluorophenyl)sulfonyl]amino]acetyl]amino]benzoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: SH-4-54 is an inhibitor of signal transducer and activator of transcription 3 (STAT3; IC50 = 4.7 μM for STAT3 homodimer DNA binding activity). It selectively inhibits STAT3 homodimer over STAT1 and STAT5 homodimer and STAT3:STAT1 heterodimer DNA binding in EGF-stimulated NIH3T3/hEGFR nuclear extracts containing activated STAT1, STAT3, and STAT5 and decreases STAT3 iNOS, Survivin, and Bcl-2 promoter occupancy in MDA-MB-231 cells. SH-4-54 inhibits growth of glioma, breast, and prostate cancer cell lines that express constitutively active STAT3 (IC50s = 1-7.4, 3.8-4.5, and 5.3-5.8 μM, respectively). In vivo, SH-4-54 (3 mg/kg per day) inhibits tumor growth in the U251MG glioma and MDA-MB-231 breast cancer mouse xenograft models.
• Uses: 4-[[(4-Cyclohexylphenyl)methyl][2-[methyl[(2,3,4,5,6-pentafluorophenyl)sulfonyl]amino]acetyl]amino]benzoic Acid acts as a STAT 3 and STAT5 inhibitor. STAT 3 is unusually active in glioblastoma and plays a crucial role in tumor growth

Technology Process of SH-4-54

There total 8 articles about SH-4-54 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: 86.0%

benzyl 4-(N-(4-cyclohexylbenzyl)-2-(2,3,4,5,6-pentafluoro-N-methylphenylsulfonamido)acetamido)benzoate → SH-4-54 (1456632-40-8)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; methanol; for 3.08333h;

DOI:10.1021/ml4003138

Reference yield:

benzyl 4-aminobenzoate (19008-43-6) → SH-4-54 (1456632-40-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: acetic acid / 1,2-dichloro-ethane / 0.08 h / 20 °C / Molecular sieve

2.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C

3.1: dichlorotriphenylphosphorane / chloroform / 0.08 h / 20 °C

3.2: 0.25 h / 125 °C / Microwave irradiation

4.1: palladium 10% on activated carbon; hydrogen / methanol; tetrahydrofuran / 3.08 h

With palladium 10% on activated carbon; hydrogen; sodium tris(acetoxy)borohydride; acetic acid; dichlorotriphenylphosphorane; In tetrahydrofuran; methanol; chloroform; 1,2-dichloro-ethane;

DOI:10.1021/ml4003138

Reference yield:

benzyl 4-((4-cyclohexylbenzyl)amino)benzoate → SH-4-54 (1456632-40-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dichlorotriphenylphosphorane / chloroform / 0.08 h / 20 °C

1.2: 0.25 h / 125 °C / Microwave irradiation

2.1: palladium 10% on activated carbon; hydrogen / methanol; tetrahydrofuran / 3.08 h

With palladium 10% on activated carbon; hydrogen; dichlorotriphenylphosphorane; In tetrahydrofuran; methanol; chloroform;

DOI:10.1021/ml4003138

upstream raw materials:

benzyl 4-aminobenzoate

pentafluorobenzenesulonyl chloride

4-amino-benzoic acid

Refernces