1-ethyl-4,7-dimethoxy-2-(2-naphthyl)-1H-benzimidazole | 1246929-34-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-ethyl-4,7-dimethoxy-2-(2-naphthyl)-1H-benzimidazole
• 英文别名: 1-Ethyl-4,7-dimethoxy-2-naphthalen-2-ylbenzimidazole
• CAS: 1246929-34-9
• 化学式: C₂₁H₂₀N₂O₂
• 分子量: 332.402
• InChiKey: IODGDKLYXXGLHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-ethyl-4,7-dimethoxy-2-(2-naphthyl)-1H-benzimidazole 在 氢溴酸 、 iron(III) chloride 作用下， 以 水 为溶剂， 反应 21.0h， 以77%的产率得到1-ethyl-2-(2-naphthyl)-1H-benzimidazole-4,7-dione
  参考文献：
  名称：

  Synthesis and toxicity towards normal and cancer cell lines of benzimidazolequinones containing fused aromatic rings and 2-aromatic ring substituents

  摘要：

  A facile 6-exo-trig cyclization of sigma-aromatic radicals has allowed the synthesis of various aromatic ring fused benzimidazoles and benzimidazolequinones. The most highly conjugated naphthyl fused benzimidazolequinone, (5-methyl-5,6-dihydrobenzimidazo[2,1-a]benzo[f]isoquinoline-8,11-dione) showed the highest specificity towards human cervical (HeLa) and prostate (DU145) cancer cell lines with little toxicity towards a human normal (GM00637) cell line at doses of <1 mu M. In contrast, 2-aromatic ring substituted (benzimidazole-4,7-diones) analogues, benzimidazolequinone with a pyridine ring and mitomycin C were more toxic than the highly conjugated naphthyl fused benzimidazolequinone towards the normal cell line. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.05.025
• 作为产物：
  描述：

  4,7-dimethoxy-2-(2-naphthyl)-1H-benzimidazole 、 碘乙烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以60%的产率得到1-ethyl-4,7-dimethoxy-2-(2-naphthyl)-1H-benzimidazole
  参考文献：
  名称：

  Synthesis and toxicity towards normal and cancer cell lines of benzimidazolequinones containing fused aromatic rings and 2-aromatic ring substituents

  摘要：

  A facile 6-exo-trig cyclization of sigma-aromatic radicals has allowed the synthesis of various aromatic ring fused benzimidazoles and benzimidazolequinones. The most highly conjugated naphthyl fused benzimidazolequinone, (5-methyl-5,6-dihydrobenzimidazo[2,1-a]benzo[f]isoquinoline-8,11-dione) showed the highest specificity towards human cervical (HeLa) and prostate (DU145) cancer cell lines with little toxicity towards a human normal (GM00637) cell line at doses of <1 mu M. In contrast, 2-aromatic ring substituted (benzimidazole-4,7-diones) analogues, benzimidazolequinone with a pyridine ring and mitomycin C were more toxic than the highly conjugated naphthyl fused benzimidazolequinone towards the normal cell line. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.05.025

文献信息

• Synthesis and toxicity towards normal and cancer cell lines of benzimidazolequinones containing fused aromatic rings and 2-aromatic ring substituents
  作者：Eoin Moriarty、Miriam Carr、Sarah Bonham、Michael P. Carty、Fawaz Aldabbagh

  DOI：10.1016/j.ejmech.2010.05.025

  日期：2010.9

  A facile 6-exo-trig cyclization of sigma-aromatic radicals has allowed the synthesis of various aromatic ring fused benzimidazoles and benzimidazolequinones. The most highly conjugated naphthyl fused benzimidazolequinone, (5-methyl-5,6-dihydrobenzimidazo[2,1-a]benzo[f]isoquinoline-8,11-dione) showed the highest specificity towards human cervical (HeLa) and prostate (DU145) cancer cell lines with little toxicity towards a human normal (GM00637) cell line at doses of <1 mu M. In contrast, 2-aromatic ring substituted (benzimidazole-4,7-diones) analogues, benzimidazolequinone with a pyridine ring and mitomycin C were more toxic than the highly conjugated naphthyl fused benzimidazolequinone towards the normal cell line. (C) 2010 Elsevier Masson SAS. All rights reserved.