(5S)-5-ethyl-3-isopropoxy-5-methyl-4-[4-(methylsulfonyl)phenyl]furan-2(5H)-thione | 853658-46-5

• 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: (5S)-5-ethyl-3-isopropoxy-5-methyl-4-[4-(methylsulfonyl)phenyl]furan-2(5H)-thione
• 英文别名: (5S)-5-ethyl-5-methyl-4-(4-methylsulfonylphenyl)-3-propan-2-yloxyfuran-2-thione
• CAS: 853658-46-5
• 化学式: C₁₇H₂₂O₄S₂
• 分子量: 354.491
• InChiKey: XBTUAQBIXABBLS-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  93.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5S)-5-ethyl-3-isopropoxy-5-methyl-4-[4-(methylsulfonyl)phenyl]furan-2(5H)-thione 在 4-二甲氨基吡啶 、 silver trifluoromethanesulfonate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 Sodium 4-({(7S)-7-ethyl-9-isopropoxy-7-methyl-8-[4-(methylsulfonyl)phenyl]-1,4,6-trioxaspiro[4.4]non-8-en-2-yl}methoxy)-4-oxobutanoate
  参考文献：
  名称：

  Novel approach to pro-drugs of lactones: water soluble imidate and ortho-ester derivatives of a furanone-based COX-2 selective inhibitor

  摘要：

  Interest in water soluble COX-2 inhibitors that can be administered intravenously led to the development of novel pro-drugs of a furanone based COX-2 inhibitor 2. Transforming the lactone moiety of the furanone to an imidate or an ortho-ester with a hydrophilic, endogenous appendage resulted in water soluble pro-drugs that converted to the parent drug in vivo. © 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.009
• 作为产物：
  描述：

  (S)-5-ethyl-5-methyl-3-(1-methylethoxy)-4-[(4-methylsulfonyl)phenyl]-3-oxolen-2-one 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以95%的产率得到(5S)-5-ethyl-3-isopropoxy-5-methyl-4-[4-(methylsulfonyl)phenyl]furan-2(5H)-thione
  参考文献：
  名称：

  Water soluble prodrugs of COX-2 inhibitors

  摘要：

  揭示了作为COX-2抑制剂的前药有用的水溶性化合物，以及包含它们的药物组合物。

  公开号：

  US20060189682A1

文献信息

• Water soluble prodrugs of COX-2 inhibitors
  申请人：Payne E. Joseph

  公开号：US20060189682A1

  公开（公告）日：2006-08-24

  Disclosed are water soluble compounds which are useful as prodrugs of COX-2 inhibitors, and pharmaceutical compositions comprising them.

  揭示了作为COX-2抑制剂的前药有用的水溶性化合物，以及包含它们的药物组合物。
• Novel approach to pro-drugs of lactones: water soluble imidate and ortho-ester derivatives of a furanone-based COX-2 selective inhibitor
  作者：Steve F. Poon、Nicholas Stock、Joseph E. Payne、Angela R. McGuire、Brian Stearns、Xiaoqing Yang、Weichao Chen、Benito Munoz、Nicholas D. Smith

  DOI：10.1016/j.bmcl.2005.03.009

  日期：2005.5

  Interest in water soluble COX-2 inhibitors that can be administered intravenously led to the development of novel pro-drugs of a furanone based COX-2 inhibitor 2. Transforming the lactone moiety of the furanone to an imidate or an ortho-ester with a hydrophilic, endogenous appendage resulted in water soluble pro-drugs that converted to the parent drug in vivo. © 2005 Elsevier Ltd. All rights reserved.