methyl 5-[(2-methyl-1H-indol-3-yl)thio]-1H-benzoimidazol-2-ylcarbamate

• 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: methyl 5-[(2-methyl-1H-indol-3-yl)thio]-1H-benzoimidazol-2-ylcarbamate
• 英文别名: methyl N-[6-[(2-methyl-1H-indol-3-yl)sulfanyl]-1H-benzimidazol-2-yl]carbamate
• 化学式: C₁₈H₁₆N₄O₂S
• 分子量: 352.417
• InChiKey: HTUDFSLOSQEIIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 5-[(2-methyl-1H-indol-3-yl)thio]-1H-benzoimidazol-2-ylcarbamate 在 间氯过氧苯甲酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以69%的产率得到methyl 5-[(2-methyl-1H-indol-3-yl)sulfonyl]-1H-benzoimidazol-2-ylcarbamate
  参考文献：
  名称：

  Synthesis and evaluation of benzimidazole carbamates bearing indole moieties for antiproliferative and antitubulin activities

  摘要：

  A series of novel benzimidazole carbamates bearing indole moieties with sulphur or selenium atoms connecting the aromatic rings were synthesised and evaluated for their antiproliferative activities against three human cancer cell lines (SGC-7901. A-549 and HT-1080) using an MTT assay. Compounds 10a, 10b, 7a, 7b and 7f showed significant activities against these cell lines. The most potent compound in this series, 10a, was selected to investigate its antitumour mechanism. In addition, molecular docking studies suggested that compound 10a interacts very closely with the nocodazole docking pose through hydrogen bonds at the colchicine binding site of tubulin. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.071
• 作为产物：
  描述：

  2-methyl-3-thiocyanato-1H-indole 在 iron(III) chloride 、 sodium tetrahydroborate 、 sodium 、 甲烷 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 4.67h， 生成 methyl 5-[(2-methyl-1H-indol-3-yl)thio]-1H-benzoimidazol-2-ylcarbamate
  参考文献：
  名称：

  Synthesis and evaluation of benzimidazole carbamates bearing indole moieties for antiproliferative and antitubulin activities

  摘要：

  A series of novel benzimidazole carbamates bearing indole moieties with sulphur or selenium atoms connecting the aromatic rings were synthesised and evaluated for their antiproliferative activities against three human cancer cell lines (SGC-7901. A-549 and HT-1080) using an MTT assay. Compounds 10a, 10b, 7a, 7b and 7f showed significant activities against these cell lines. The most potent compound in this series, 10a, was selected to investigate its antitumour mechanism. In addition, molecular docking studies suggested that compound 10a interacts very closely with the nocodazole docking pose through hydrogen bonds at the colchicine binding site of tubulin. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.071

文献信息

• Synthesis and evaluation of benzimidazole carbamates bearing indole moieties for antiproliferative and antitubulin activities
  作者：Qi Guan、Chunming Han、Daiying Zuo、Min'an Zhai、Zengqiang Li、Qian Zhang、Yanpeng Zhai、Xuewei Jiang、Kai Bao、Yingliang Wu、Weige Zhang

  DOI：10.1016/j.ejmech.2014.09.071

  日期：2014.11

  A series of novel benzimidazole carbamates bearing indole moieties with sulphur or selenium atoms connecting the aromatic rings were synthesised and evaluated for their antiproliferative activities against three human cancer cell lines (SGC-7901. A-549 and HT-1080) using an MTT assay. Compounds 10a, 10b, 7a, 7b and 7f showed significant activities against these cell lines. The most potent compound in this series, 10a, was selected to investigate its antitumour mechanism. In addition, molecular docking studies suggested that compound 10a interacts very closely with the nocodazole docking pose through hydrogen bonds at the colchicine binding site of tubulin. (C) 2014 Elsevier Masson SAS. All rights reserved.