N-[(1-tritylaziridin-(2S)-yl)methyl]-1H-benzimidazole-4,7-dione | 1095273-29-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N-[(1-tritylaziridin-(2S)-yl)methyl]-1H-benzimidazole-4,7-dione
• 英文别名: 1-[[(2S)-1-tritylaziridin-2-yl]methyl]benzimidazole-4,7-dione
• CAS: 1095273-29-2
• 化学式: C₂₉H₂₃N₃O₂
• 分子量: 445.521
• InChiKey: NASRDRWUOMAFBA-IFIVVKAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4,7-dimethoxy-N-[(1-tritylaziridin-(2S)-yl)methyl]-1H-benzimidazole 在 N-溴代丁二酰亚胺(NBS) 、 硫酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.67h， 以56%的产率得到N-[(1-tritylaziridin-(2S)-yl)methyl]-1H-benzimidazole-4,7-dione
  参考文献：
  名称：

  The influence of the aziridinyl substituent of benzimidazoles and benzimidazolequinones on toxicity towards normal and Fanconi anaemia cells

  摘要：

  Aziridinyl substituted benzimidazolequinones are more toxic than methoxy analogues towards normal human fibroblast cells (GM00637). The aziridinyl substituent is required for hypersensitive killing of Fanconi anaemia (FA) cells (PD20i) deficient in FANCD2. Despite lacking quinone functionality, 4,7-dimethoxy-N-[(aziridin-2-yl)methyl]benzimidazole also induces hypersensitivity from FA cells, similar to their response towards mitomycin C. Expression of FANCD2 (in PD20:RV) corrects FA cell hypersensitivity supporting cellular response via the FANC pathway. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.01.026

文献信息

• First synthesis of N-[(aziridin-2-yl)methyl]benzimidazolequinone and analysis of toxicity towards normal and Fanconi anemia cells
  作者：Liz O’Donovan、Michael P. Carty、Fawaz Aldabbagh

  DOI：10.1039/b814706j

  日期：——

  A diazole is N-substituted with 1-trityl-2-methylaziridine and demethylated and oxidised with NBS under acidic conditions to give a benzimidazolequinone; this novel anti-tumour agent is marginally more cytotoxic than mitomycin C (MMC) towards the normal human fibroblast cell line GM00637, while the MMC-hypersensitive human Fanconi anaemia (FA) cell line, PD20i, lacking the FANCD2 protein, is also hypersensitive to the benzimidazolequinone, with expression of FANCD2 protein decreasing sensitivity to both MMC and the benzimidazolequinone.

  在酸性条件下，用 1-三苯甲基-2-甲基氮丙啶对重氮唑进行 N-取代、脱甲基和 NBS 氧化，得到苯并咪唑醌；这种新型抗肿瘤药物对正常人成纤维细胞系 GM00637 的细胞毒性略高于丝裂霉素 C（MMC），而对 MMC 不敏感的人范可尼贫血（FA）细胞系 PD20i（缺乏 FANCD2 蛋白）对苯并咪唑醌也不敏感，FANCD2 蛋白的表达会降低对 MMC 和苯并咪唑醌的敏感性。
• The influence of the aziridinyl substituent of benzimidazoles and benzimidazolequinones on toxicity towards normal and Fanconi anaemia cells
  作者：Karen Fahey、Liz O'Donovan、Miriam Carr、Michael P. Carty、Fawaz Aldabbagh

  DOI：10.1016/j.ejmech.2010.01.026

  日期：2010.5

  Aziridinyl substituted benzimidazolequinones are more toxic than methoxy analogues towards normal human fibroblast cells (GM00637). The aziridinyl substituent is required for hypersensitive killing of Fanconi anaemia (FA) cells (PD20i) deficient in FANCD2. Despite lacking quinone functionality, 4,7-dimethoxy-N-[(aziridin-2-yl)methyl]benzimidazole also induces hypersensitivity from FA cells, similar to their response towards mitomycin C. Expression of FANCD2 (in PD20:RV) corrects FA cell hypersensitivity supporting cellular response via the FANC pathway. (C) 2010 Elsevier Masson SAS. All rights reserved.