(2S)-4-chloro-S-(4-methylphenyl)-3-oxo-1-phenylbutane-2-sulfonamido

• ChemBase编号: 137300
• 分子式: C17H18ClNO3S
• 平均质量: 351.84772
• 单一同位素质量: 351.06959212
• SMILES: Cc1ccc(cc1)S(=O)(=O)N[C@@H](Cc1ccccc1)C(=O)CCl
• Canonical SMILES: ClCC(=O)[C@@H](NS(=O)(=O)c1ccc(cc1)C)Cc1ccccc1
• InChI: InChI=1S/C17H18ClNO3S/c1-13-7-9-15(10-8-13)23(21,22)19-16(17(20)12-18)11-14-5-3-2-4-6-14/h2-10,16,19H,11-12H2,1H3/t16-/m0/s1
• InChIKey: MQUQNUAYKLCRME-INIZCTEOSA-N

名称和登记号

名称

• IUPAC标准名: (2S)-4-chloro-S-(4-methylphenyl)-3-oxo-1-phenylbutane-2-sulfonamido
• IUPAC传统名: TPCK
• 别名: (S)-1-Chloro-3-tosylamido-4-phenyl-2-butanone; (S)-1-Chloro-4-phenyl-3-tosylamido-2-butanone; N-p-Tosyl-L-phenylalanine chloromethyl ketone; TPCK; Tosyl-L-phenylalanyl-chloromethane; L-1-p-Tosylamino-2-phenylethyl chloromethyl ketone; N-p-Tosyl-L-phenylalanine chloromethyl ketone

登记号

• CAS号: 402-71-1
• EC号: 206-954-6
• MDL号: MFCD00000935
• Beilstein号: 2895215
• PubChem SID: 24278737; 162231564
• PubChem CID: 439647

理论计算性质

• Acid pKa: 10.168556
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 3.886409
• LogD (pH = 7.4): 3.8857622
• Log P: 3.8864174
• 摩尔折射率: 91.6556 cm^3
• 极化性: 36.23309 Å^3
• 极化表面积: 63.24 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO: >10 mg/mL (stable for several months at 4°C.); ethanol: soluble20 mg/mL (stable for several months at 4°C. Stock solutions (10 mM in methanol or ethanol) are stable for several months at 4°C.)
• 外观: white powder
• 熔点: 106-108 °C(lit.)

安全信息

• RTECS编号: XT5613500
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 37/38-41
• 安全公开号: 26-36
• GHS危险品标识: GHS05; GHS07
• GHS警示词: Danger
• GHS危险声明: H315-H318-H335
• GHS警示性声明: P261-P280-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: -20°C

药理学性质

• 相关基因信息: human ... NFKB1(4790), NKAP(79576), NKRF(55922), NOS2(4843), PTGS2(5743)

产品相关信息

• 纯度: ≥97% (TLC); ≥99%
• 药效: 10-100 μM effective concentration
• 线性分子式: C6H5CH2CH(NHSO2C6H4CH3)COCH2Cl
• Empirical Formula (Hill Notation): C17H18ClNO3S

详细说明

Sigma Aldrich - T4376

Application
Irreversible inhibitor of certain serine proteases; used to inhibit chymotrypsin in preparations of trypsin.
Caution
Shelf-life is at least two years when stored desiccated at -20 °C.
Biochem/physiol Actions
Blocks the LPS- or cytokine-induced activation of nuclear factor κB (NFκB), which, in turn, blocks the induction of iNOS and COX-2 transcription. Blocks activation of pp70s6k by all mitogens. Blocks apoptosis cell lines by inhibiting the processing of caspases in some cell lines and to some stimuli. Also blocks apoptosis initiated by Taxol (in MCF-7 human breast carcinoma cells).1

Sigma Aldrich - 857254

Application
Protease inhibitor.