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

• ChemBase编号: 133304
• 分子式: C16H19BrN2OS
• 平均质量: 367.30386
• 单一同位素质量: 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

名称和登记号

名称

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

登记号

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

理论计算性质

• Acid pKa: 15.250456
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 2.7600198
• LogD (pH = 7.4): 3.5309336
• Log P: 3.55956
• 摩尔折射率: 96.4317 cm^3
• 极化性: 31.972496 Å^3
• 极化表面积: 44.16 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO: soluble20 mg/mL
• 外观: off-white powder
• 熔点: 192.1-192.5 °C(lit.)

安全信息

• 保存条件: protect from light; under inert gas
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: -20°C

药理学性质

• 作用靶点: p53

产品相关信息

• 纯度: ≥95% (HPLC)
• 成盐信息: HBr
• 运输包装: wet ice

详细说明

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.