6-[(E)-1-(4-methylsulfanylphenyl)but-1-en-3-ynyl]-1-propan-2-ylsulfonylbenzimidazol-2-amine | 186092-72-8

• 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-[(E)-1-(4-methylsulfanylphenyl)but-1-en-3-ynyl]-1-propan-2-ylsulfonylbenzimidazol-2-amine
• CAS: 186092-72-8
• 化学式: C₂₁H₂₁N₃O₂S₂
• 分子量: 411.549
• InChiKey: PKVMLEDRQCPCAJ-NGYBGAFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-[(E)-1-(4-methylsulfanylphenyl)but-1-en-3-ynyl]-1-propan-2-ylsulfonylbenzimidazol-2-amine 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到6-[(E)-1-(4-methylsulfonylphenyl)but-1-en-3-ynyl]-1-propan-2-ylsulfonylbenzimidazol-2-amine
  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：

  (3,4-二氨基苯)(4-氟苯)甲酮 在 吡啶 、 sodium hydroxide 、 dicobalt octacarbonyl 、 mercuric acid 、 magnesium 、 ferric nitrate 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 、 二氯甲烷 、 异丙醇 、 甲苯 、 乙腈 为溶剂， 反应 6.5h， 生成 6-[(E)-1-(4-methylsulfanylphenyl)but-1-en-3-ynyl]-1-propan-2-ylsulfonylbenzimidazol-2-amine
  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.