(2S)-2,6-bis[(4-fluorophenyl)sulfonylamino]hexanoic acid | 1042421-62-4

• 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: (2S)-2,6-bis[(4-fluorophenyl)sulfonylamino]hexanoic acid
• CAS: 1042421-62-4
• 化学式: C₁₈H₂₀F₂N₂O₆S₂
• 分子量: 462.495
• InChiKey: WCQZXULHSJMWNH-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  146
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2S)-2,6-bis[(4-fluorophenyl)sulfonylamino]hexanoic acid 、 O-苄基羟胺 在 N-羟基-7-氮杂苯并三氮唑 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 C₂₅H₂₇F₂N₃O₆S₂
  参考文献：
  名称：

  Novel bis-(arylsulfonamide) hydroxamate-based selective MMP inhibitors

  摘要：

  A series of bis-(arylsulfonamide) hydroxamate inhibitors were synthesized. These compounds exhibit good potency against MMP-7 and MMP-9 depending on the nature, steric bulk, and substitution pattern of the substituents in the benzene ring. In general, the preliminary structure-activity relationships (SAR) suggest that among the DAPA hydroxamates (i) electron-rich benzene rings of the sulfonamides may produce better inhibitors than electron-poor analogs. However, potential H-bond acceptors can reverse the trend depending on the isozyme; (ii) isozyme selectivity between MMP-7 and-9 can be conferred through steric bulk and substitution pattern of the substituents in the benzene ring, and (iii) the MMP-10 inhibition pattern of the compounds paralleled that for MMP-9. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.04.035
• 作为产物：
  描述：

  L-赖氨酸 、 4-氟苯磺酰氯 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 (2S)-2,6-bis[(4-fluorophenyl)sulfonylamino]hexanoic acid
  参考文献：
  名称：

  Novel bis-(arylsulfonamide) hydroxamate-based selective MMP inhibitors

  摘要：

  A series of bis-(arylsulfonamide) hydroxamate inhibitors were synthesized. These compounds exhibit good potency against MMP-7 and MMP-9 depending on the nature, steric bulk, and substitution pattern of the substituents in the benzene ring. In general, the preliminary structure-activity relationships (SAR) suggest that among the DAPA hydroxamates (i) electron-rich benzene rings of the sulfonamides may produce better inhibitors than electron-poor analogs. However, potential H-bond acceptors can reverse the trend depending on the isozyme; (ii) isozyme selectivity between MMP-7 and-9 can be conferred through steric bulk and substitution pattern of the substituents in the benzene ring, and (iii) the MMP-10 inhibition pattern of the compounds paralleled that for MMP-9. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.04.035

文献信息

• Novel bis-(arylsulfonamide) hydroxamate-based selective MMP inhibitors
  作者：Rajesh Subramaniam、Manas K. Haldar、Shakila Tobwala、Bratati Ganguly、D.K. Srivastava、Sanku Mallik

  DOI：10.1016/j.bmcl.2008.04.035

  日期：2008.6

  A series of bis-(arylsulfonamide) hydroxamate inhibitors were synthesized. These compounds exhibit good potency against MMP-7 and MMP-9 depending on the nature, steric bulk, and substitution pattern of the substituents in the benzene ring. In general, the preliminary structure-activity relationships (SAR) suggest that among the DAPA hydroxamates (i) electron-rich benzene rings of the sulfonamides may produce better inhibitors than electron-poor analogs. However, potential H-bond acceptors can reverse the trend depending on the isozyme; (ii) isozyme selectivity between MMP-7 and-9 can be conferred through steric bulk and substitution pattern of the substituents in the benzene ring, and (iii) the MMP-10 inhibition pattern of the compounds paralleled that for MMP-9. (C) 2008 Elsevier Ltd. All rights reserved.