5-(3-benzenesulfonamidophenyl)-N-hydroxypent-2-en-4-ynamide

• ChemBase编号: 154272
• 分子式: C17H14N2O4S
• 平均质量: 342.36906
• 单一同位素质量: 342.06742794
• SMILES: c1ccc(cc1)S(=O)(=O)Nc1cccc(c1)C#C/C=C/C(=O)NO
• Canonical SMILES: ONC(=O)/C=C/C#Cc1cccc(c1)NS(=O)(=O)c1ccccc1
• InChI: InChI=1S/C17H14N2O4S/c20-17(18-21)12-5-4-7-14-8-6-9-15(13-14)19-24(22,23)16-10-2-1-3-11-16/h1-3,5-6,8-13,19,21H,(H,18,20)
• InChIKey: QRPSQQUYPMFERG-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 5-(3-benzenesulfonamidophenyl)-N-hydroxypent-2-en-4-ynamide; (2E)-5-(3-benzenesulfonamidophenyl)-N-hydroxypent-2-en-4-ynamide
• IUPAC传统名: 5-(3-benzenesulfonamidophenyl)-N-hydroxypent-2-en-4-ynamide; (2E)-5-(3-benzenesulfonamidophenyl)-N-hydroxypent-2-en-4-ynamide
• 别名: (2E)-5-[3-(Phenylsulfonylamino)phenyl]-pent-2-en-4-ynohydroxamic acid; Oxamflatin; (2E)-N-Hydroxy-5-[3-[(phenylsulfonyl)amino]phenyl]-2-penten-4-ynamide; (2E)-5-[3-(Phenylsulfonylamino)phenyl]pent-2-en-4-ynohydroxamic Acid; Oxamflatin

登记号

• CAS号: 151720-43-3
• MDL号: MFCD00949087
• PubChem SID: 162248411
• PubChem CID: 5353852

理论计算性质

• Acid pKa: 7.7770977
• 质子受体: 4
• 质子供体: 3
• LogD (pH = 5.5): 2.2027388
• LogD (pH = 7.4): 2.071371
• Log P: 2.2047713
• 摩尔折射率: 89.1108 cm^3
• 极化性: 34.896065 Å^3
• 极化表面积: 95.5 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO; DMSO: soluble13 mg/mL; Ethyl Acetate; Methanol
• 外观: Red-Brown Solid; solid
• 熔点: 98-100°C

安全信息

• 保存条件: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• 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: 2-8°C

产品相关信息

• 纯度: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C17H14N2O4S

详细说明

Sigma Aldrich - O3139

Biochem/physiol Actions
Histone deacetylase inhibitor; anti-cancer agent.

Toronto Research Chemicals - O845090

Histone deacetylase inhibitor. A cell-permeable, aromatic sulfonamide derivative with a hydroxamic acid group that potently inhibits mammalian HDAC by binding to the active site zinc.

参考文献

• Ohtani, M., et al.: J. Med. Chem., 39, 2871 (1996)
• Dear, A.E., et al.: Biochem. Biophys. Acta, 1492, 15 (1996)
• Lavoie, R., et al.: Bioorg. Med. Chem. Lett., 11, 2847 (1996)