6-tert-butyl-7-thiocyanato-1,4-dihydro-quinoxaline-2,3-dione | 261712-32-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 6-tert-butyl-7-thiocyanato-1,4-dihydro-quinoxaline-2,3-dione
• 英文别名: (7-tert-butyl-2,3-dioxo-1,4-dihydroquinoxalin-6-yl) thiocyanate
• CAS: 261712-32-7
• 化学式: C₁₃H₁₃N₃O₂S
• 分子量: 275.331
• InChiKey: GYHHKHJPYIBTGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-tert-butyl-7-thiocyanato-1,4-dihydro-quinoxaline-2,3-dione 在 sodium tetrahydroborate 、 sodium hydrogensulfide 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 6-tert-butyl-7-mercapto-1,4-dihydro-quinoxaline-2,3-dione
  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
• 作为产物：
  描述：

  5-tert-Butyl-2-nitro-4-thiocyanato-phenylamine 在 镍 吡啶 、 氢气 作用下， 以 四氢呋喃 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 32.0h， 生成 6-tert-butyl-7-thiocyanato-1,4-dihydro-quinoxaline-2,3-dione
  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：Warner-Lambert Company

  公开号：US06528510B1

  公开（公告）日：2003-03-04

  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.

  本发明涉及具有改进药理特性的新型带有连环杂环的二氢吡喃，能有效抑制HIV天冬氨酸蛋白酶，阻断HIV的感染性。这些二氢吡喃在开发治疗病毒感染和疾病，包括艾滋病的疗法方面是有用的。本发明还涉及合成这些二氢吡喃的方法，以及在制备最终化合物中有用的中间体。
• HIV PROTEASE INHIBITORS
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP1112269A2

  公开（公告）日：2001-07-04
• 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
• [EN] HIV PROTEASE INHIBITORS<br/>[FR] INHIBITEURS DE LA PROTEASE DU VIH
  申请人：WARNER LAMBERT CO

  公开号：WO2000015634A2

  公开（公告）日：2000-03-23

  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.