3,3,3-Trifluoro-2-[(4-phenoxyphenyl)sulfanylmethyl]-2-(propylamino)propanoic acid | 866553-63-1

• 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)sulfanylmethyl]-2-(propylamino)propanoic acid
• 英文别名: 3,3,3-trifluoro-2-[(4-phenoxyphenyl)sulfanylmethyl]-2-(propylamino)propanoic acid
• CAS: 866553-63-1
• 化学式: C₁₉H₂₀F₃NO₃S
• 分子量: 399.434
• InChiKey: UEIAJGJUYIWYNJ-UHFFFAOYSA-N

物化性质

• 沸点：
  478.2±45.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  83.9
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,3,3-Trifluoro-2-[(4-phenoxyphenyl)sulfanylmethyl]-2-(propylamino)propanoic acid 在 palladium dihydroxide 氢气 、 间氯过氧苯甲酸 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 4.0h， 生成 3,3,3-trifluoro-N-hydroxy-2-[(4-phenoxyphenyl)sulfonylmethyl]-2-(propylamino)propanamide
  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：

  4-溴茴香硫醚 在 氢氧化钾 、 氢溴酸 、 sodium hydride 、 caesium carbonate 、 间氯过氧苯甲酸 、 三氟乙酸酐 、 sodium iodide 、 copper(l) chloride 、 lithium diisopropyl amide 作用下， 以 N-甲基吡咯烷酮 、 甲醇 、 氯仿 、 水 、 溶剂黄146 、 丙酮 为溶剂， 反应 4.0h， 生成 3,3,3-Trifluoro-2-[(4-phenoxyphenyl)sulfanylmethyl]-2-(propylamino)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

文献信息

• Synthesis of α-trifluoromethyl-α-amino-β-sulfone hydroxamates: novel nanomolar inhibitors of matrix metalloproteinases
  作者：Roberta Sinisi、Monica Sani、Gabriele Candiani、Rachele Parente、Françoise Pecker、Stefano Bellosta、Matteo Zanda

  DOI：10.1016/j.tetlet.2005.07.078

  日期：2005.9

  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.