tert-butyl 2-(4-[1,2,4]triazol-4-ylphenylthio)-5-[2-(4-oxo-4H-benzo[d][1,2,3]triazin-3-ylmethyl)]-cyclopentanecarboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: tert-butyl 2-(4-[1,2,4]triazol-4-ylphenylthio)-5-[2-(4-oxo-4H-benzo[d][1,2,3]triazin-3-ylmethyl)]-cyclopentanecarboxylate
• 英文别名: tert-butyl (1R,2R,5S)-2-[(4-oxo-1,2,3-benzotriazin-3-yl)methyl]-5-[4-(1,2,4-triazol-4-yl)phenyl]sulfanylcyclopentane-1-carboxylate
• 化学式: C₂₆H₂₈N₆O₃S
• 分子量: 504.613
• InChiKey: VICJLUCJAVGMKB-RTFZILSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  127
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-(4-[1,2,4]triazol-4-ylphenylthio)-5-[2-(4-oxo-4H-benzo[d][1,2,3]triazin-3-ylmethyl)]-cyclopentanecarboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以68%的产率得到2-(4-[1,2,4]triazol-4-ylphenylthio)-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 、 偶氮二甲酸二异丙酯 、 三苯基膦 、 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 103.5h， 生成 tert-butyl 2-(4-[1,2,4]triazol-4-ylphenylthio)-5-[2-(4-oxo-4H-benzo[d][1,2,3]triazin-3-ylmethyl)]-cyclopentanecarboxylate
  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.