6-tert-Butyl-5-(toluene-4-sulfonylsulfanyl)-1H-indole-2-carboxylic acid ethyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 6-tert-Butyl-5-(toluene-4-sulfonylsulfanyl)-1H-indole-2-carboxylic acid ethyl ester
• 英文别名: ethyl 6-tert-butyl-5-(4-methylphenyl)sulfonylsulfanyl-1H-indole-2-carboxylate
• 化学式: C₂₂H₂₅NO₄S₂
• 分子量: 431.577
• InChiKey: BEEDWRXFPXFBNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-叔丁基甲苯 在 吡啶 、 sodium tetrahydroborate 、 sodium hydrogensulfide 、 乙醇 、 硫酸 、 溴 、 硝酸 、 氢化钾 、 铁粉 、 溶剂黄146 作用下， 以 甲醇 、 四氯化碳 、 乙醚 为溶剂， 反应 38.0h， 生成 6-tert-Butyl-5-(toluene-4-sulfonylsulfanyl)-1H-indole-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis of Heterocyclic Thiosulfonates

  摘要：

  [formula: see text] A simple synthesis of heterocyclic thiosulfonates containing indole, indoline, benzoimidazole, and quinoxaline rings is described. The synthesis of these thiosulfonates involves the preparation of the appropriately substituted thiols followed by sulfonylation to give thiosulfonates. The corresponding thiols were prepared in a simple and efficient manner by using a thiocyanation reaction either prior to heterocycle ring formation or after heterocycle ring formation. These thiosulfonates were coupled successfully to the 5,6-dihydropyran-2-one ring to give products that showed excellent HIV protease activity.

  DOI：

  10.1021/ol0056170

文献信息

• HIV protease inhibitors
  申请人：——

  公开号：US20040106606A1

  公开（公告）日：2004-06-03

  The present invention relates to novel dihydropyrones with tethered heterocycles having improved pharmacologic properties which potently inhibit the HIV aspartyl protease blocking HIV infectivity. The dihydropyrones are useful in the development of therapies for the treatment of viral infections and diseases including AIDS. The present invention is also directed to methods of synthesis of the dihydropyrones and intermediates useful in the preparation of the final compounds.

  本发明涉及一种新颖的具有改进药理学性质的带有连接杂环的二氢吡喃并具有强烈抑制HIV天冬氨酸蛋白酶以阻止HIV感染性的药物。这些二氢吡喃可用于开发治疗病毒感染和疾病，包括艾滋病的治疗方案。本发明还涉及二氢吡喃的合成方法以及用于制备最终化合物的中间体。
• US6528510B1
  申请人：——

  公开号：US6528510B1

  公开（公告）日：2003-03-04
• US6852711B2
  申请人：——

  公开号：US6852711B2

  公开（公告）日：2005-02-08
• Synthesis of Heterocyclic Thiosulfonates
  作者：J. V. N. Vara Prasad

  DOI：10.1021/ol0056170

  日期：2000.4.1

  [formula: see text] A simple synthesis of heterocyclic thiosulfonates containing indole, indoline, benzoimidazole, and quinoxaline rings is described. The synthesis of these thiosulfonates involves the preparation of the appropriately substituted thiols followed by sulfonylation to give thiosulfonates. The corresponding thiols were prepared in a simple and efficient manner by using a thiocyanation reaction either prior to heterocycle ring formation or after heterocycle ring formation. These thiosulfonates were coupled successfully to the 5,6-dihydropyran-2-one ring to give products that showed excellent HIV protease activity.