[2-Amino-3-(propane-2-sulfonyl)-3H-benzoimidazol-5-yl]-(4-methoxy-phenyl)-methanone | 1026649-63-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [2-Amino-3-(propane-2-sulfonyl)-3H-benzoimidazol-5-yl]-(4-methoxy-phenyl)-methanone
• 英文别名: (2-Amino-3-propan-2-ylsulfonylbenzimidazol-5-yl)-(4-methoxyphenyl)methanone
• CAS: 1026649-63-7
• 化学式: C₁₈H₁₉N₃O₄S
• 分子量: 373.433
• InChiKey: ZYOVKTZODCNPJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [2-Amino-3-(propane-2-sulfonyl)-3H-benzoimidazol-5-yl]-(4-methoxy-phenyl)-methanone 在 盐酸 、 potassium tert-butylate 、 magnesium 、 mercury dichloride 作用下， 以 四氢呋喃 、 二甲基亚砜 、 乙酸乙酯 、 甲苯 为溶剂， 反应 3.5h， 生成 6-[(E)-1-(4-Methoxy-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：

  3,4-二硝基苯甲酸 在 镍 吡啶 、 sodium hydroxide 、 三氯化铝 、 五氯化磷 、 氢气 作用下， 以 四氢呋喃 、 二氯甲烷 、 异丙醇 、 乙腈 为溶剂， 25.0~50.0 ℃ 、413.69 kPa 条件下， 反应 14.92h， 生成 [2-Amino-3-(propane-2-sulfonyl)-3H-benzoimidazol-5-yl]-(4-methoxy-phenyl)-methanone
  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.