Pifithrin-alpha
Title: Pifithrin-a
CAS Registry Number: 63208-82-2
CAS Name: 1-(4-Methylphenyl)-2-(4,5,6,7-tetrahydro-2-imino-3(2H)-benzothiazolyl)ethanone monohydrobromide
Additional Names: 2-(2-imino-4,5,6,7-tetrahydrobenzothiazol-3-yl)-1-p-tolylethanone hydrobromide; PFT-a
Molecular Formula: C16H18N2OS.HBr
Molecular Weight: 367.30
Percent Composition: C 52.32%, H 5.21%, N 7.63%, O 4.36%, S 8.73%, Br 21.75%
Literature References: Small molecule inhibitor of p53-mediated gene activation and apoptosis; the name pifithrin is an abbreviation for p-fifty three inhibitor. Converted in vitro to the planar tricyclic condensation product, pifithrin-b. Prepn: A. Singh et al., Indian J. Chem. 14B, 997 (1976). Identification of p53 inhibition: P. G. Komarov et al., Science 285, 1733 (1999). Synthesis and neuroprotective activity: X. Zhu et al., J. Med. Chem. 45, 5090 (2002). Inhibition of heat shock and glucocorticoid signal transduction pathways: E. A. Komarova et al., J. Biol. Chem. 278, 15465 (2003). Characterization as an aryl hydrocarbon receptor agonist: M. S. Hoagland et al., J. Pharmacol. Exp. Ther. 314, 603 (2005). Conversion to pifithrin-b: R. K. Gary, D. A. Jensen, Mol. Pharm. 2, 462 (2005).
Properties: mp 182°. pKa 9.11. Sol in water, DMSO.
Melting point: mp 182°
pKa: pKa 9.11
 
Derivative Type: Pifithrin-b
CAS Registry Number: 60477-34-1; 511296-88-1 (hydrobromide)
CAS Name: 5,6,7,8-Tetrahydro-2-(4-methylphenyl)imidazo[2,1-b]benzothiazole
Additional Names: 2-(4-methylphenyl)imidazo[2,1b]-5,6,7,8-tetrahydrobenzothiazole; 2-p-tolyl-5,6,7,8-tetrahydrobenzo[d]imidazo[2,1-b]thiazole; cyclic pifithrin-a
Molecular Formula: C16H16N2S
Molecular Weight: 268.38
Percent Composition: C 71.60%, H 6.01%, N 10.44%, S 11.95%
Literature References: Crystal structure: W. Clegg, C. Jamieson, Acta Crystallogr. E61, o1486 (2005).
Properties: Crystals from methanol. mp 185°. pKa 4.36. Log P (octanol/water): 4.26. Crystal density: 1.318 Mg/m3.
Melting point: mp 185°
pKa: pKa 4.36
Log P: Log P (octanol/water): 4.26
 
Use: Biochemical tool in studies of p53 function and apoptosis.

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