γ-trifluoromethyl γ-sulfone hydroxamate | 851370-99-5

• 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: γ-trifluoromethyl γ-sulfone hydroxamate
• 英文别名: Butanamide, 4,4,4-trifluoro-N-hydroxy-3-[(4-methoxyphenyl)sulfonyl]-；4,4,4-trifluoro-N-hydroxy-3-(4-methoxyphenyl)sulfonylbutanamide
• CAS: 851370-99-5
• 化学式: C₁₁H₁₂F₃NO₅S
• 分子量: 327.281
• InChiKey: FDARNXMDMOELTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4,4,4-Trifluoro-3-(4-methoxy-phenylsulfanyl)-butyric acid 在 palladium dihydroxide 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 氯仿 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 27.0h， 生成 γ-trifluoromethyl γ-sulfone hydroxamate
  参考文献：
  名称：

  Novel highly potent, structurally simple γ-trifluoromethyl γ-sulfone hydroxamate inhibitor of stromelysin-1 (MMP-3)

  摘要：

  The gamma-trifluoromethyl gamma-sulfone hydroxamate 1 was synthesized both in racemic and enantiomerically pure forms by means of a thia-Michael reaction of p-methoxythiophenol on achiral and chiral 3,3,3-trifluorocrotonoyl Michael acceptors. The (R)-1 enantiomer was the most potent inhibitor of MMP-3 (stromelysin-1), showing an IC50 = 3.2 nM, as well as the most selective with respect to MMP-9 (65-fold). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.02.063

文献信息

• Novel highly potent, structurally simple γ-trifluoromethyl γ-sulfone hydroxamate inhibitor of stromelysin-1 (MMP-3)
  作者：Monica Sani、Gabriele Candiani、Françoise Pecker、Luciana Malpezzi、Matteo Zanda

  DOI：10.1016/j.tetlet.2005.02.063

  日期：2005.4

  The gamma-trifluoromethyl gamma-sulfone hydroxamate 1 was synthesized both in racemic and enantiomerically pure forms by means of a thia-Michael reaction of p-methoxythiophenol on achiral and chiral 3,3,3-trifluorocrotonoyl Michael acceptors. The (R)-1 enantiomer was the most potent inhibitor of MMP-3 (stromelysin-1), showing an IC50 = 3.2 nM, as well as the most selective with respect to MMP-9 (65-fold). (c) 2005 Elsevier Ltd. All rights reserved.