N-(6-Bromo-benzothiazol-2-yl)-2-dibutylamino-acetamide | 36935-78-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(6-Bromo-benzothiazol-2-yl)-2-dibutylamino-acetamide
• 英文别名: N-(6-bromo-1,3-benzothiazol-2-yl)-2-(dibutylamino)acetamide
• CAS: 36935-78-1
• 化学式: C₁₇H₂₄BrN₃OS
• 分子量: 398.367
• InChiKey: ABYJDZPORCPQGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  73.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-溴苯胺 在 苯甲酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 26.5h， 生成 N-(6-Bromo-benzothiazol-2-yl)-2-dibutylamino-acetamide
  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

• 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.