5,6-dihydrophenanthridin-6-one

• ChemBase编号: 68417
• 分子式: C13H9NO
• 平均质量: 195.21666
• 单一同位素质量: 195.06841391
• SMILES: c1cccc2[nH]c(=O)c3ccccc3c12
• Canonical SMILES: O=c1[nH]c2ccccc2c2c1cccc2
• InChI: InChI=1S/C13H9NO/c15-13-11-7-2-1-5-9(11)10-6-3-4-8-12(10)14-13/h1-8H,(H,14,15)
• InChIKey: RZFVLEJOHSLEFR-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 5,6-dihydrophenanthridin-6-one
• IUPAC传统名: 5H-phenanthridin-6-one
• 别名: 6(5H)-5-氮杂菲酮; 6-(5H)-菲啶酮; 6(5H)-Phenanthridinone; 5H-Phenanthridin-6-one; 6-Phenanthridinol; 6-Phenanthridinone; 6-Phenanthridone; PJ 97A; 6(5H)-Phenanthridinone; WD 99-004344; 6-Phenanthridone; phenanthridin-6(5H)-one; 6-(5H)-Phenanthridinone; 6(5H)-Phenanthridinone; NSC 11021; NSC 40943; NSC 61083; 6-(5H)-Phenanthridinone

登记号

• CAS号: 1015-89-0
• EC号: 213-804-3
• MDL号: MFCD00004988
• Beilstein号: 140641
• PubChem SID: 24858050; 162034148
• PubChem CID: 1853

理论计算性质

• Acid pKa: 13.477064
• 质子受体: 1
• 质子供体: 1
• LogD (pH = 5.5): 2.7391102
• LogD (pH = 7.4): 2.7391098
• Log P: 2.7391102
• 摩尔折射率: 60.6697 cm^3
• 极化性: 23.630543 Å^3
• 极化表面积: 29.1 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: 288-294°C; 290 - 292°C; 290-292 °C(lit.)
• 疏水性(logP): 2.196

安全信息

• 保存注意事项: IRRITANT
• RTECS编号: SG0370000
• 德国WGK号: 3
• TSCA收录: false; 否
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

药理学性质

• 相关基因信息: human ... PARP1(142)

产品相关信息

• 纯度: 95%; 95+%; 96%; 98%
• 级别: technical grade
• Empirical Formula (Hill Notation): C13H9NO

详细说明

Sigma Aldrich - 299634

包装
1 g in glass bottle
Application
Reactant involved in:
• Synthesis of 5,6-dihydrophenanthridine sulfonamides1
• Oxidative coupling with diphenylacetylene2
• Direct copper acetate-catalyzed N-cyclopropylation of cyclic amides3Reactant involved in the synthesis and/or pharmacological activity of biologically active molecules including:
• Potassium channel KV1.3 and IK-1 inhibitors4
• HIV-1 integrase inhibitors5

Toronto Research Chemicals - P294900

6-Phenanthridone is a poly(ADP-ribose) polymerase (PARP) inhibitor with immunosuppressive effects. 6-Phenanthridone has been shown to inhibit concanavalin A-induced lymphocyte proliferation.

参考文献

• Chiarugi, A. et al.: Br. J. Pharmacol., 137, 761 (2002)
• Nasrabady, S.E. et al.: Cell. Mol. Neurobiol., 31, 503 (2002)
• Weltin, D. et al.: Int. J. Immunopharmacol., 17, 265 (2002)