5-methyl-2-(6-methyl-pyridin-2-yl)-1(3)H-benzoimidazole | 67273-47-6

• 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-methyl-2-(6-methyl-pyridin-2-yl)-1(3)H-benzoimidazole
• 英文别名: Benzimidazole, 5-methyl-2-(6-methyl-2-pyridyl)-；6-methyl-2-(6-methylpyridin-2-yl)-1H-benzimidazole
• CAS: 67273-47-6
• 化学式: C₁₄H₁₃N₃
• 分子量: 223.277
• InChiKey: OKHWNVWJPUHVKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-methyl-2-(6-methyl-pyridin-2-yl)-1(3)H-benzoimidazole 在 palladium on activated charcoal 硫酸 、 氢气 、 溴 、 硝酸 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 110.0 ℃ 、344.74 kPa 条件下， 反应 12.67h， 生成 5-Methyl-2-(6-methyl-pyridin-2-yl)-1H-benzoimidazol-4-ylamine
  参考文献：
  名称：

  Differential antiproliferative activity of new benzimidazole-4,7-diones

  摘要：

  Ten benzimidazole-4,7-diones were synthesized and tested in vitro on two tumor cell lines. Several compounds showed a significant antiproliferative activity on K562 cells, although to a different extent, whereas compound 1i showed a highly significant activity on SW620 cells, comparable to that of doxorubicin. Both the substituents in the quinone ring and the position of the nitrogen atom in the pyridine moiety play a crucial role for the biological activity.

  DOI：

  10.1016/j.farmac.2004.04.001
• 作为产物：
  描述：

  4-甲基-2-硝基苯胺 在 tin(ll) chloride 作用下， 以 甲醇 、 硝基苯 为溶剂， 反应 5.0h， 生成 5-methyl-2-(6-methyl-pyridin-2-yl)-1(3)H-benzoimidazole
  参考文献：
  名称：

  Differential antiproliferative activity of new benzimidazole-4,7-diones

  摘要：

  Ten benzimidazole-4,7-diones were synthesized and tested in vitro on two tumor cell lines. Several compounds showed a significant antiproliferative activity on K562 cells, although to a different extent, whereas compound 1i showed a highly significant activity on SW620 cells, comparable to that of doxorubicin. Both the substituents in the quinone ring and the position of the nitrogen atom in the pyridine moiety play a crucial role for the biological activity.

  DOI：

  10.1016/j.farmac.2004.04.001

文献信息

• 2-Substituted azole derivatives. 1. Synthesis and antiinflammatory activity of some 2-(substituted-pyridinyl)benzimidazoles
  作者：Goro Tsukamoto、Koichiro Yoshino、Toshihiko Kohno、Hiroshi Ohtaka、Hajime Kagaya、Keizo Ito

  DOI：10.1021/jm00181a007

  日期：1980.7

  A series of 2-(2-pyridinyl)benzimidazoles was synthesized and evaluated for antiinflammatory activity by the carrageenan-induced rat paw edema assay. Among several active derivatives, 2-(5-ethylpyridin-2-yl)benzimidazole (6) was selected for further study. A comparison of compound 6 with phenylbutazone and tiaramide revealed that 6 possesses stronger activity in acute inflammatory models possibly with

  合成了一系列的2-（2-吡啶基）苯并咪唑，并通过角叉菜胶诱导的大鼠爪水肿试验评估了其抗炎活性。在几种活性衍生物中，选择2-（5-乙基吡啶-2-基）苯并咪唑（6）进行进一步研究。化合物6与苯基丁a和噻草胺的比较表明，在急性炎症模型中，化合物6具有比苯基丁a和噻草胺稍强的胃肠道刺激性。
• BENZIMIDAZOLE DERIVATES USEFUL AS INHIBITORS OF MAMMALIAN HISTONE DEACETYLASE ACTIVITY
  申请人：Kancera AB

  公开号：EP3294715B1

  公开（公告）日：2020-05-06
• Differential antiproliferative activity of new benzimidazole-4,7-diones
  作者：Laura Garuti、Marinella Roberti、Daniela Pizzirani、Annalisa Pession、Emanuela Leoncini、Valentina Cenci、Silvana Hrelia

  DOI：10.1016/j.farmac.2004.04.001

  日期：2004.8

  Ten benzimidazole-4,7-diones were synthesized and tested in vitro on two tumor cell lines. Several compounds showed a significant antiproliferative activity on K562 cells, although to a different extent, whereas compound 1i showed a highly significant activity on SW620 cells, comparable to that of doxorubicin. Both the substituents in the quinone ring and the position of the nitrogen atom in the pyridine moiety play a crucial role for the biological activity.