2,3-bis(1-(dimethylamino)naphthalene-5-sulfonamido)-N-hydroxypropanamide | 1042421-29-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,3-bis(1-(dimethylamino)naphthalene-5-sulfonamido)-N-hydroxypropanamide
• 英文别名: 2,3-bis[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]-N-hydroxypropanamide
• CAS: 1042421-29-3
• 化学式: C₂₇H₃₁N₅O₆S₂
• 分子量: 585.705
• InChiKey: CZJNIILYDQDLMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  165
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  在 5% Pd/C 、 氢气 作用下， 以 四氢呋喃 为溶剂， 以46%的产率得到2,3-bis(1-(dimethylamino)naphthalene-5-sulfonamido)-N-hydroxypropanamide
  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.