2,3-bis(4-chlorophenylsulfonamido)-N-hydroxypropanamide | 220391-36-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3-bis(4-chlorophenylsulfonamido)-N-hydroxypropanamide
• 英文别名: 2,3-bis[(4-chlorophenyl)sulfonylamino]-N-hydroxypropanamide
• CAS: 220391-36-6
• 化学式: C₁₅H₁₅Cl₂N₃O₆S₂
• 分子量: 468.339
• InChiKey: YPKIDRAXEHHNGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  158
• 氢给体数：
  4
• 氢受体数：
  8

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72%的产率得到2,3-bis(4-chlorophenylsulfonamido)-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

• SULFONYLAMINO SUBSTITUTED HYDROXAMIC ACID DERIVATIVES AS METALLOPROTEASE INHIBITORS
  申请人：THE PROCTER & GAMBLE COMPANY

  公开号：EP1009737A2

  公开（公告）日：2000-06-21
• US6218389B1
  申请人：——

  公开号：US6218389B1

  公开（公告）日：2001-04-17
• [EN] ACYCLIC METALLOPROTEASE INHIBITORS<br/>[FR] INHIBITEURS DE METALLOPROTEASE ACYCLIQUES
  申请人：——

  公开号：WO1999006340A2

  公开（公告）日：1999-02-11

  [EN] The invention provides compounds of formula (I) as described in the claims, or an optical isomer, diastereomer or enantiomer thereof, or a pharmaceutically-acceptable salt, or biohydrolyzable amide, ester, or imide thereof are useful as inhibitors of metalloproteases. Also disclosed are pharmaceutical compositions and methods of treating diseases, disorders and conditions characterized by metalloprotease activity using these compounds or the pharmaceutical compositions containing them.
  [FR] L'invention concerne des composés de la formule (I) telle que décrite dans les revendications, ou un isomère optique, un diastéréomère ou un énantiomère, un sel acceptable du point de vue pharmaceutique, un amide, un ester ou un imide pouvant être biohydrolysé, de ces composés, s'utilisant comme inhibiteurs de métalloprotéases. L'invention concerne en outre des compositions pharmaceutiques et des méthodes de traitement de maladies, de troubles et d'affections se caractérisant par une activité des métalloprotéases, au moyen de ces compositions ou des compositions pharmaceutiques les contenant.
• 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.