methyl N-[6-(hexylsulfamoyl)-1H-benzimidazol-2-yl]carbamate | 350688-42-5

• 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 N-[6-(hexylsulfamoyl)-1H-benzimidazol-2-yl]carbamate
• CAS: 350688-42-5
• 化学式: C₁₅H₂₂N₄O₄S
• 分子量: 354.43
• InChiKey: ZQEUBZTXHYMBNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl N-[6-(hexylsulfamoyl)-1H-benzimidazol-2-yl]carbamate 、 C.I.酸性橙108 在 吡啶 作用下， 反应 3.0h， 生成 N-hexyl-2-(3-(2-hydroxyethyl)ureido)-1H-benzo[d]imidazole-5-sulfonamide
  参考文献：
  名称：

  Design and synthesis of novel benzoheterocyclic derivatives as human acrosin inhibitors by scaffold hopping

  摘要：

  Human acrosin is an attracting target for the development of novel male contraceptives. Scaffold hopping was used to optimize the isoxazolecarbaldehyde human acrosin inhibitors and extend their structure-activity relationships. Four kinds of scaffolds, namely benzimidazole, benzothiazole, 3H-indazole, and 5-phenyl-1H-pyrazole, were designed and synthesized. Most of the synthesized compounds showed potent human acrosin inhibitory activity and their binding modes were investigated by molecular docking. The scaffold of the compounds was found to be important for the inhibitory activity. Several compounds were more active than the positive control TLCK, suggesting that they can serve as good starting points for the discovery of novel male contraceptive agents. (C) 2012 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2012.11.005
• 作为产物：
  描述：

  甲基1H-苯并咪唑-2-基氨基甲酸酯 在 氯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 生成 methyl N-[6-(hexylsulfamoyl)-1H-benzimidazol-2-yl]carbamate
  参考文献：
  名称：

  Design and synthesis of novel benzoheterocyclic derivatives as human acrosin inhibitors by scaffold hopping

  摘要：

  Human acrosin is an attracting target for the development of novel male contraceptives. Scaffold hopping was used to optimize the isoxazolecarbaldehyde human acrosin inhibitors and extend their structure-activity relationships. Four kinds of scaffolds, namely benzimidazole, benzothiazole, 3H-indazole, and 5-phenyl-1H-pyrazole, were designed and synthesized. Most of the synthesized compounds showed potent human acrosin inhibitory activity and their binding modes were investigated by molecular docking. The scaffold of the compounds was found to be important for the inhibitory activity. Several compounds were more active than the positive control TLCK, suggesting that they can serve as good starting points for the discovery of novel male contraceptive agents. (C) 2012 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2012.11.005

文献信息

• Synthesis and acrosin inhibitory activity of methyl 5-substituted-1H-benzo[d]imidazol-2-yl carbamate derivatives
  作者：Xuefei Liu、Qianqian Chen、Ju Zhu、Yongzheng Fan、Lili Ding、Juntao Zhao、Guangqian Han、Wei Tian、Jingjing Qi、Youjun Zhou、Jiaguo Lv

  DOI：10.1016/j.bmcl.2012.03.042

  日期：2012.5

  A series of novel methyl 5-substituted 1H-benzo[d]imidazol-2-ylcarbamates were designed, synthesized, and their acrosin inhibitory activities evaluated in vitro. The results of acrosin inhibitory activity showed that all title compounds were more potent than the control TLCK. Compound 4w displayed the most potent acrosin inhibitory activity among all the compounds, with an IC50 of 6.3 x 10 (5) M. The studies provide a new structural class for the development of novel acrosin inhibitory agents. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.
• Design and synthesis of novel benzoheterocyclic derivatives as human acrosin inhibitors by scaffold hopping
  作者：Qianqian Chen、Wei Tian、Guangqian Han、Jingjing Qi、Canhui Zheng、Youjun Zhou、Lili Ding、Juntao Zhao、Ju Zhu、Jiaguo Lv、Chunquan Sheng

  DOI：10.1016/j.ejmech.2012.11.005

  日期：2013.1

  Human acrosin is an attracting target for the development of novel male contraceptives. Scaffold hopping was used to optimize the isoxazolecarbaldehyde human acrosin inhibitors and extend their structure-activity relationships. Four kinds of scaffolds, namely benzimidazole, benzothiazole, 3H-indazole, and 5-phenyl-1H-pyrazole, were designed and synthesized. Most of the synthesized compounds showed potent human acrosin inhibitory activity and their binding modes were investigated by molecular docking. The scaffold of the compounds was found to be important for the inhibitory activity. Several compounds were more active than the positive control TLCK, suggesting that they can serve as good starting points for the discovery of novel male contraceptive agents. (C) 2012 Published by Elsevier Masson SAS.