2-(2-imino-2,3,4,5,6,7-hexahydro-1,3-benzothiazol-3-yl)-1-(4-methylphenyl)ethan-1-one hydrobromide

• ChemBase ID: 133304
• Molecular Formular: C16H19BrN2OS
• Molecular Mass: 367.30386
• Monoisotopic Mass: 366.04014624
• SMILES: Cc1ccc(cc1)C(=O)Cn1c2c(sc1=N)CCCC2.Br
• Canonical SMILES: Cc1ccc(cc1)C(=O)Cn1c(=N)sc2c1CCCC2.Br
• InChI: InChI=1S/C16H18N2OS.BrH/c1-11-6-8-12(9-7-11)14(19)10-18-13-4-2-3-5-15(13)20-16(18)17;/h6-9,17H,2-5,10H2,1H3;1H
• InChIKey: HAGVCKULCLQGRF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2-imino-2,3,4,5,6,7-hexahydro-1,3-benzothiazol-3-yl)-1-(4-methylphenyl)ethan-1-one hydrobromide
• IUPAC Traditional name: 2-(2-imino-4,5,6,7-tetrahydro-1,3-benzothiazol-3-yl)-1-(4-methylphenyl)ethanone hydrobromide
• Synonyms: 2-(2-Imino-4,5,6,7-tetrahydrobenzothiazol-3-yl)-1-p-tolylethanone hydrobromide; PFT-α; Pifithrin-α; Pifithrin-α

Database IDs

• CAS Number: 63208-82-2
• MDL Number: MFCD00417851
• PubChem SID: 162227581; 24898529
• PubChem CID: 9929138

CALCULATED PROPERTIES

• Acid pKa: 15.250456
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.7600198
• LogD (pH = 7.4): 3.5309336
• Log P: 3.55956
• Molar Refractivity: 96.4317 cm^3
• Polarizability: 31.972496 Å^3
• Polar Surface Area: 44.16 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble20 mg/mL
• Apperance: off-white powder
• Melting Point: 192.1-192.5 °C(lit.)

Safety Information

• Storage Condition: protect from light; under inert gas
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Target: p53

Product Information

• Purity: ≥95% (HPLC)
• Salt Data: HBr
• Shipped in: wet ice

DETAILS

Sigma Aldrich - P4359

Biochem/physiol Actions
Pifithrin-α is a reversible inhibitor of p53-mediated apoptosis and p53-dependent gene transcription such as cyclin G, p21/waf1, and mdm2 expression. Pifithrin-α enhances cell survival after genotoxic stress such as UV irradiation and treatment with cytotoxic compounds including doxorubicin, etopoxide, paclitaxel, and cytosine-β-D-arabinofuranoside. Pifithrin-α protects mice from lethal whole body γ-irradiation without an increase in cancer incidence. The protective effect is not seen in p53-null mice or cells expressing a dominant negative mutant of the p53 gene. Protection is conferred by the transient expression of p53 in p53-deficient cell lines.