3,3,3-Trifluoro-2-[(4-phenoxyphenyl)sulfonylmethyl]-2-(phenylmethoxycarbonylamino)propanoic acid | 866553-35-7

• 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: 3,3,3-Trifluoro-2-[(4-phenoxyphenyl)sulfonylmethyl]-2-(phenylmethoxycarbonylamino)propanoic acid
• 英文别名: 3,3,3-trifluoro-2-[(4-phenoxyphenyl)sulfonylmethyl]-2-(phenylmethoxycarbonylamino)propanoic acid
• CAS: 866553-35-7
• 化学式: C₂₄H₂₀F₃NO₇S
• 分子量: 523.487
• InChiKey: OWZYUVRETRRKSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3,3,3-Trifluoro-2-[(4-phenoxyphenyl)sulfonylmethyl]-2-(phenylmethoxycarbonylamino)propanoic acid 在 palladium dihydroxide 氢气 、 N,N-二异丙基乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 α-trifluoromethyl-α-amino-β-sulfone hydroxamate
  参考文献：
  名称：

  Synthesis of α-trifluoromethyl-α-amino-β-sulfone hydroxamates: novel nanomolar inhibitors of matrix metalloproteinases

  摘要：

  The racemic alpha-trifluoromethyl-alpha-amino-beta-sulfone hydroxamates 1 were synthesized by means of a nucleophilic addition of sulfur-stabilized carbanions to a N-Cbz imine of trifluoropyruvate (4). The free amino derivative 1a was the most potent inhibitor of both MMP-3 (stromelysin-1) and MMP-9 (gelatinase-B), showing an IC50 = 14 nM and 1 nM, respectively, and excellent selectivity versus MMP- 1 (>5000-fold difference in inhibitory capacity). The N-Me derivative 1b was the most selective for MMP-3 with respect to MMP-9 (62-fold difference). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.078
• 作为产物：
  描述：

  1-甲烷磺酰基-4-苯氧基苯 在 sodium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.17h， 生成 3,3,3-Trifluoro-2-[(4-phenoxyphenyl)sulfonylmethyl]-2-(phenylmethoxycarbonylamino)propanoic acid
  参考文献：
  名称：

  Synthesis of α-trifluoromethyl-α-amino-β-sulfone hydroxamates: novel nanomolar inhibitors of matrix metalloproteinases

  摘要：

  The racemic alpha-trifluoromethyl-alpha-amino-beta-sulfone hydroxamates 1 were synthesized by means of a nucleophilic addition of sulfur-stabilized carbanions to a N-Cbz imine of trifluoropyruvate (4). The free amino derivative 1a was the most potent inhibitor of both MMP-3 (stromelysin-1) and MMP-9 (gelatinase-B), showing an IC50 = 14 nM and 1 nM, respectively, and excellent selectivity versus MMP- 1 (>5000-fold difference in inhibitory capacity). The N-Me derivative 1b was the most selective for MMP-3 with respect to MMP-9 (62-fold difference). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.078