Pifithrin-alpha

Base Information

• Chemical Name: Pifithrin-alpha
• CAS No.: 63208-82-2
• Molecular Formula: C16H19BrN2OS
• Molecular Weight: 367.31
• UNII: D213B92S1Y
• DSSTox Substance ID: DTXSID10432994
• Wikipedia: Pifithrin
• Wikidata: Q3915126
• Pharos Ligand ID: 1BHLHCD3GRYB
• ChEMBL ID: CHEMBL556353
• Mol file: 63208-82-2.mol

Synonyms:1-(4-methylphenyl)-2-(4,5,6,7-tetrahydro-2-imino-3(2H)- benzothiazolyl)ethanone hydrobromide;1-(4-methylphenyl)-2-(4,5,6,7-tetrahydro-2-imino-3(2H)-benzothiazolyl)ethanone hydrobromide (1:1);2-(2-imino-4,5,6,7-tetrahydrobenzothiazol-3-yl)-1-p-tolylethanone;ethanone, 1-(4-methylphenyl)-2-(4,5,6,7-tetrahydro-2-imino-3(2H)-benzothiazolyl)-, hydrobromide (1:1);PFT alpha;pifithrin;pifithrin-alpha

Chemical Property of Pifithrin-alpha

Chemical Property:

• Vapor Pressure: 1.57E-08mmHg at 25°C
• Melting Point: 192.1-192.5 °C(lit.)
• Refractive Index: 1.666
• Boiling Point: 456.8°C at 760 mmHg
• PKA: 9.11(at 25℃)
• Flash Point: 230.1°C
• PSA: 74.09000
• Density: 1.28g/cm³
• LogP: 4.15700
• Storage Temp.: −20°C
• Solubility.: DMSO: 20 mg/mL
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 366.04015
• Heavy Atom Count: 21
• Complexity: 449

Purity/Quality:

99% ^*data from raw suppliers

Pifithrin-alpha hydrobromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)C(=O)CN2C3=C(CCCC3)SC2=N.Br
• Description: Pifithrin-α is an inactivator of p53 that blocks p53-dependent transcriptional activation and apoptosis. It prevents p53-mediated apoptosis induced by cytotoxic compounds in C8 cells at 10 μM and in human umbilical vein endothelial cells at 30 μM. Pifithrin-α can also protect cells from DNA damage-induced apoptosis by a p53-independent mechanism that might involve cyclin D1.
• Uses: Pifithrin-α has been used:to study the effect of specific p53 inhibitor on p53-upregulated modulator of apoptosis (PUMA) expression after transient global cerebral ischemia (tGCI)as p53 inhibitor to treat PA1 cellsas a tumor protein p53 (TRP53) inhibitor, to treat mouse lung epithelial-12 (MLE-12) cells

Technology Process of Pifithrin-alpha

There total 4 articles about Pifithrin-alpha 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: 70.0%

2-Amino-4,5,6,7-tetrahydrobenzothiazole (2933-29-1) + 4-(bromoacetyl)toluene (619-41-0) → pifithrin-α (63208-82-2)

Guidance literature:

In benzene; at 21 ℃; for 48h;

Reference yield:

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → pifithrin-α (63208-82-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 52 percent / iodine / 12 h / 110 °C

2: 54 percent / toluene / 48 h / 20 °C

With iodine; In toluene;

DOI:10.1016/j.bmcl.2005.01.075

Reference yield:

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → pifithrin-α (63208-82-2)

Guidance literature:

Multi-step reaction with 2 steps

1: iodine / 6 h / 100 °C / Sealed tube

2: benzene / 48 h / 21 °C

With iodine; In benzene;

upstream raw materials:

2-Amino-4,5,6,7-tetrahydrobenzothiazole

4-(bromoacetyl)toluene

cyclohexanone

Downstream raw materials:

cyclic pifithrin-α

2-(4-methylphenyl)-5,6,7,8-tetrahydrobenzo[d]-imidazo[2,1-b]thiazole

Refernces

• 1、 Pietrancosta, Nicolas,Moumen, Anice,Dono, Rosanna,Lingor, Paul,Planchamp, Veronique,Lamballe, Fabienne,B?hr, Mathias,Kraus, Jean-Louis,Maina, Flavio. "Imino-tetrahydro-benzothiazole derivatives as p53 inhibitors: Discovery of a highly potent in vivo inhibitor and its action mechanism". . p. 3645 - 3652. Retrieved 2007/10/03.
• 2、 Barchéchath, Sylvie D.,Tawatao, Rommel I.,Corr, Maripat,Carson, Dennis A.,Cottam, Howard B.. "Inhibitors of apoptosis in lymphocytes: Synthesis and biological evaluation of compounds related to pifithrin-α". . p. 6409 - 6422. Retrieved 2007/10/03.