5,6-dihydro-10-nitrobenzimidazo[2,1-a]isoquinoline-8-carboxamide N-oxide | 1350542-55-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 5,6-dihydro-10-nitrobenzimidazo[2,1-a]isoquinoline-8-carboxamide N-oxide
• 英文别名: 10-Nitro-12-oxido-5,6-dihydrobenzimidazolo[2,1-a]isoquinolin-12-ium-8-carboxamide
• CAS: 1350542-55-0
• 化学式: C₁₆H₁₂N₄O₄
• 分子量: 324.296
• InChiKey: YZUUZEZGOIMVFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,5-dinitro-2-(1,2,3,4-tetrahydroisoquinolin-2-yl)benzamide 以 丙酸 为溶剂， 反应 17.0h， 以89%的产率得到5,6-dihydro-10-nitrobenzimidazo[2,1-a]isoquinoline-8-carboxamide N-oxide
  参考文献：
  名称：

  The synthesis of 2-nitroaryl-1,2,3,4-tetrahydroisoquinolines, nitro-substituted 5,6-dihydrobenzimidazo[2,1-a]isoquinoline N-oxides and related heterocycles as potential bioreducible substrates for the enzymes NAD(P)H: quinone oxidoreductase 1 and E. coli nitroreductase

  摘要：

  A series of 2-nitroaryl-1,2,3,4-tetrahydroisoquinolines 10 and nitro-substituted 5,6-dihydrobenzimidazo[2,1-a]isoquinoline N-oxides 11 have been synthesised and evaluated as potential bioreducible substrates for the enzymes NAD(P)H: quinone oxidoreductase 1 (NQO1) and Escherichia coli nitroreductase (NR). Also prepared and evaluated were 2-(3,5-dinitropyridin-2-yl)-1,2,3,4-tetrahydroisoquinoline 12 and 5,6-dihydro-10-nitropyrido[3 '',2 '':4',5']imidazo[2',1'-a] isoquinoline 12-oxide 13. Both compounds 10b and 13 were reduced faster by human NQO1 than by CB-1954 [5-(aziridin-1-yl)-2,4-dinitrobenzamide]. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.044

文献信息

• The synthesis of 2-nitroaryl-1,2,3,4-tetrahydroisoquinolines, nitro-substituted 5,6-dihydrobenzimidazo[2,1-a]isoquinoline N-oxides and related heterocycles as potential bioreducible substrates for the enzymes NAD(P)H: quinone oxidoreductase 1 and E. coli nitroreductase
  作者：Philip J. Burke、Lai Chun Wong、Terence C. Jenkins、Richard J. Knox、Stephen P. Stanforth

  DOI：10.1016/j.bmcl.2011.10.044

  日期：2011.12

  A series of 2-nitroaryl-1,2,3,4-tetrahydroisoquinolines 10 and nitro-substituted 5,6-dihydrobenzimidazo[2,1-a]isoquinoline N-oxides 11 have been synthesised and evaluated as potential bioreducible substrates for the enzymes NAD(P)H: quinone oxidoreductase 1 (NQO1) and Escherichia coli nitroreductase (NR). Also prepared and evaluated were 2-(3,5-dinitropyridin-2-yl)-1,2,3,4-tetrahydroisoquinoline 12 and 5,6-dihydro-10-nitropyrido[3 '',2 '':4',5']imidazo[2',1'-a] isoquinoline 12-oxide 13. Both compounds 10b and 13 were reduced faster by human NQO1 than by CB-1954 [5-(aziridin-1-yl)-2,4-dinitrobenzamide]. (C) 2011 Elsevier Ltd. All rights reserved.