toluene-4-thiosulfonic acid S-[2-tert-butyl-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-phenyl] ester | 207737-10-8

• 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: toluene-4-thiosulfonic acid S-[2-tert-butyl-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-phenyl] ester
• 英文别名: tert-butyl-[5-tert-butyl-2-methyl-4-(4-methylphenyl)sulfonylsulfanylphenoxy]-dimethylsilane
• CAS: 207737-10-8
• 化学式: C₂₄H₃₆O₃S₂Si
• 分子量: 464.766
• InChiKey: RGROUYOEUDLEBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.47
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  77
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  toluene-4-thiosulfonic acid S-[2-tert-butyl-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-phenyl] ester 在 四丁基氟化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.25h， 生成 5-(2-tert-butyl-4-hydroxy-5-methyl-phenyl)sulfanyl-4-hydroxy-2-[2-(4-hydroxyphenyl)ethyl]-2-methyl-3H-pyran-6-one
  参考文献：
  名称：

  Nonpeptidic HIV protease inhibitors: 6-alkyl-5,6-dihydropyran-2-ones possessing a novel and achiral 3-(2-t-butyl-5-methyl-4-sulfamate)phenylthio moiety

  摘要：

  Dihydropyran-Zones possessing a sulfamate moiety at the 4-position of the thiophenyl ring were designed to reach S-3' pocket of the HIV protease. Synthetic routes for the preparation of thiotosylates possessing 3-(2-t-butyl-5-methyl-4-sulfamate) phenylthio moiety were established. SAR of various sulfamate analogs including HIV protease binding affinities, antiviral activities and therapeutic indices will be described. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00360-1
• 作为产物：
  描述：

  4-叔丁基甲苯 在 palladium on activated charcoal 咪唑 、 DL-dithiothreitol 、 K₂HPO₄ buffer 、 硫酸 、 氢气 、 溴 、 硝酸 、 三乙胺 、 sodium bromide 、 sodium nitrite 作用下， 以 甲醇 、 四氯化碳 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 80.0 ℃ 、344.74 kPa 条件下， 反应 74.5h， 生成 toluene-4-thiosulfonic acid S-[2-tert-butyl-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-phenyl] ester
  参考文献：
  名称：

  Nonpeptidic HIV protease inhibitors: 6-alkyl-5,6-dihydropyran-2-ones possessing a novel and achiral 3-(2-t-butyl-5-methyl-4-sulfamate)phenylthio moiety

  摘要：

  Dihydropyran-Zones possessing a sulfamate moiety at the 4-position of the thiophenyl ring were designed to reach S-3' pocket of the HIV protease. Synthetic routes for the preparation of thiotosylates possessing 3-(2-t-butyl-5-methyl-4-sulfamate) phenylthio moiety were established. SAR of various sulfamate analogs including HIV protease binding affinities, antiviral activities and therapeutic indices will be described. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00360-1

文献信息

• Dihydropyrones with improved antiviral activity
  申请人：Warner-Lambert Company

  公开号：US05834506A1

  公开（公告）日：1998-11-10

  This invention pertains to improved antiviral activity of 6,6-disubstituted-5,6-dihydropyran-2-ones caused by judicious placement of certain polar substituents at the 3 and/or 6 positions. The same substituents which enhance the cellular activity also diminish cytotoxicity further enhancing the desirable properties of these agents as antivirals.

  本发明涉及通过在3和/或6位置聪明地放置某些极性取代基来改善6,6-二取代-5,6-二氢吡喃-2-酮的抗病毒活性。增强细胞活性的相同取代基也减少细胞毒性，进一步增强这些药物作为抗病毒剂的理想性能。