6-((Z)-3-Chloro-1-phenyl-buta-1,3-dienyl)-1-(propane-2-sulfonyl)-1H-benzoimidazol-2-ylamine | 189060-96-6

• 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: 6-((Z)-3-Chloro-1-phenyl-buta-1,3-dienyl)-1-(propane-2-sulfonyl)-1H-benzoimidazol-2-ylamine
• 英文别名: 6-[(1Z)-3-chloro-1-phenylbuta-1,3-dienyl]-1-propan-2-ylsulfonylbenzimidazol-2-amine
• CAS: 189060-96-6
• 化学式: C₂₀H₂₀ClN₃O₂S
• 分子量: 401.917
• InChiKey: JRCSEGQGTIHDEA-BOPFTXTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  86.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-((Z)-3-Chloro-1-phenyl-buta-1,3-dienyl)-1-(propane-2-sulfonyl)-1H-benzoimidazol-2-ylamine 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 生成 6-((Z)-1-Phenyl-but-1-en-3-ynyl)-1-(propane-2-sulfonyl)-1H-benzoimidazol-2-ylamine 、 6-((E)-1-Phenyl-but-1-en-3-ynyl)-1-(propane-2-sulfonyl)-1H-benzoimidazol-2-ylamine
  参考文献：
  名称：

  Synthesis, Antiviral Activity, and Biological Properties of Vinylacetylene Analogs of Enviroxime

  摘要：

  A series of vinylacetylene analogs of Enviroxime (1) was synthesized. The new compounds are potent inhibitors of poliovirus in tissue culture. Cross-sensitivity with Enviroxime-derived mutants shows that the new compounds have the same mechanism of action as Enviroxime, which involves the viral 3A protein. In studies with Rhesus monkeys, the p-fluoro derivative 12 was found to be unique in providing oral bioavailability. Metabolism studies using hepatic microsomes suggest that this procedure would be a useful in vitro method for selecting the appropriate animal model for testing oral absorption. Compound 12 was found to be efficacious by oral administration in treating a Coxsackie A21 infection in CD-1 mice.

  DOI：

  10.1021/jm960718i
• 作为产物：
  描述：

  2-氨基-6-苯甲酰基-1-[(异丙基)磺酰基]-1H-苯并咪唑 在 盐酸 、 magnesium 、 mercury dichloride 作用下， 以 四氢呋喃 、 乙酸乙酯 、 甲苯 为溶剂， 反应 1.5h， 生成 6-((Z)-3-Chloro-1-phenyl-buta-1,3-dienyl)-1-(propane-2-sulfonyl)-1H-benzoimidazol-2-ylamine
  参考文献：
  名称：

  Synthesis, Antiviral Activity, and Biological Properties of Vinylacetylene Analogs of Enviroxime

  摘要：

  A series of vinylacetylene analogs of Enviroxime (1) was synthesized. The new compounds are potent inhibitors of poliovirus in tissue culture. Cross-sensitivity with Enviroxime-derived mutants shows that the new compounds have the same mechanism of action as Enviroxime, which involves the viral 3A protein. In studies with Rhesus monkeys, the p-fluoro derivative 12 was found to be unique in providing oral bioavailability. Metabolism studies using hepatic microsomes suggest that this procedure would be a useful in vitro method for selecting the appropriate animal model for testing oral absorption. Compound 12 was found to be efficacious by oral administration in treating a Coxsackie A21 infection in CD-1 mice.

  DOI：

  10.1021/jm960718i

文献信息

• Synthesis, Antiviral Activity, and Biological Properties of Vinylacetylene Analogs of Enviroxime
  作者：Frantz Victor、Thomas J. Brown、Kristina Campanale、Beverly A. Heinz、Lisa A. Shipley、Kenneth S. Su、Joseph Tang、Lori M. Vance、Wayne A. Spitzer

  DOI：10.1021/jm960718i

  日期：1997.5.1

  A series of vinylacetylene analogs of Enviroxime (1) was synthesized. The new compounds are potent inhibitors of poliovirus in tissue culture. Cross-sensitivity with Enviroxime-derived mutants shows that the new compounds have the same mechanism of action as Enviroxime, which involves the viral 3A protein. In studies with Rhesus monkeys, the p-fluoro derivative 12 was found to be unique in providing oral bioavailability. Metabolism studies using hepatic microsomes suggest that this procedure would be a useful in vitro method for selecting the appropriate animal model for testing oral absorption. Compound 12 was found to be efficacious by oral administration in treating a Coxsackie A21 infection in CD-1 mice.