(1R,2R,5S)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-5-[2-(4'-fluoro-biphenyl-4-yl)-ethylsulfanyl]-cyclopentanecarboxylic acid

• 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: (1R,2R,5S)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-5-[2-(4'-fluoro-biphenyl-4-yl)-ethylsulfanyl]-cyclopentanecarboxylic acid
• 英文别名: (1R,2R,5S)-2-[(1,3-dioxoisoindol-2-yl)methyl]-5-[2-[4-(4-fluorophenyl)phenyl]ethylsulfanyl]cyclopentane-1-carboxylic acid
• 化学式: C₂₉H₂₆FNO₄S
• 分子量: 503.594
• InChiKey: DZFFLJXATZFATL-MZBJOSPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,2R,5S)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-5-[2-(4'-fluoro-biphenyl-4-yl)-ethylsulfanyl]-cyclopentanecarboxylic acid 在 二甲基二环氧乙烷 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 12.0h， 以80%的产率得到(1S,2S,5R)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-5-[2-(4'-fluoro-biphenyl-4-yl)-ethanesulfonyl]-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：

  tert-butyl 5-hydroxymethylcyclopent-1-enecarboxylate 在 哌啶 、 吡啶 、 四(三苯基膦)钯 、 18-冠醚-6 、 三氟乙酸 、 lithium chloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 179.0h， 生成 (1R,2R,5S)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-5-[2-(4'-fluoro-biphenyl-4-yl)-ethylsulfanyl]-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

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.