tert-butyl 2-(4-bromophenylthio)-5-hydroxymethylcyclopentanecarboxylate

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: tert-butyl 2-(4-bromophenylthio)-5-hydroxymethylcyclopentanecarboxylate
• 英文别名: tert-butyl (1R,2S,5R)-2-(4-bromophenyl)sulfanyl-5-(hydroxymethyl)cyclopentane-1-carboxylate
• 化学式: C₁₇H₂₃BrO₃S
• 分子量: 387.338
• InChiKey: PGMUZKXZKAIHEH-CQDKDKBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-(4-bromophenylthio)-5-hydroxymethylcyclopentanecarboxylate 在 四(三苯基膦)钯 、 偶氮二甲酸二异丙酯 、 三苯基膦 、 三氟乙酸 、 lithium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 60.0h， 生成 2-[2-(4'-chlorobiphenylthio)]-5-[2-(4-oxo-4H-benzo[d][1,2,3]triazin-3-ylmethyl)]-cyclopentanecarboxylic acid
  参考文献：
  名称：

  Stereospecific Synthesis of 5-Substituted 2-Bisarylthiocyclopentane Carboxylic Acids as Specific Matrix Metalloproteinase Inhibitors

  摘要：

  The synthesis and structure-activity relationship (SAR) studies of a series of cyclopentane carboxylic acid matrix metalloproteinase (MMP) inhibitors are described. Potent and specific MMP-2, -3, -9, -13 inhibitors were obtained by regio- and stereoselective substitutions at positions 2 and 5 on the cyclopentane ring. Compounds 2a and 2e are active in the mouse B16-F10 metastasis model and display very good pharmacokinetic parameters.

  DOI：

  10.1021/jm0307638
• 作为产物：
  描述：

  二乙基膦酰基乙酸叔丁酯 在 哌啶 、 吡啶 、 盐酸 、 lithium aluminium tetrahydride 、 正丁基锂 、 3-乙基-3-戊醇 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 85.5h， 生成 tert-butyl 2-(4-bromophenylthio)-5-hydroxymethylcyclopentanecarboxylate
  参考文献：
  名称：

  Stereospecific Synthesis of 5-Substituted 2-Bisarylthiocyclopentane Carboxylic Acids as Specific Matrix Metalloproteinase Inhibitors

  摘要：

  The synthesis and structure-activity relationship (SAR) studies of a series of cyclopentane carboxylic acid matrix metalloproteinase (MMP) inhibitors are described. Potent and specific MMP-2, -3, -9, -13 inhibitors were obtained by regio- and stereoselective substitutions at positions 2 and 5 on the cyclopentane ring. Compounds 2a and 2e are active in the mouse B16-F10 metastasis model and display very good pharmacokinetic parameters.

  DOI：

  10.1021/jm0307638

文献信息

• Stereospecific Synthesis of 5-Substituted 2-Bisarylthiocyclopentane Carboxylic Acids as Specific Matrix Metalloproteinase Inhibitors
  作者：Thierry Le Diguarher、Anne-Marie Chollet、Marc Bertrand、Philippe Hennig、Eric Raimbaud、Massimo Sabatini、Nicolas Guilbaud、Alain Pierré、Gordon C. Tucker、Patrick Casara

  DOI：10.1021/jm0307638

  日期：2003.8.1

  The synthesis and structure-activity relationship (SAR) studies of a series of cyclopentane carboxylic acid matrix metalloproteinase (MMP) inhibitors are described. Potent and specific MMP-2, -3, -9, -13 inhibitors were obtained by regio- and stereoselective substitutions at positions 2 and 5 on the cyclopentane ring. Compounds 2a and 2e are active in the mouse B16-F10 metastasis model and display very good pharmacokinetic parameters.