N'-{3-(R)-[2-(S)-(1H-indol-3-yl)-1-(methylcarbamoyl)-ethylcarbamoyl]-5-methylhexanoyl}-N-4-(4-bromophenyl)benzenesulfonylhydrazide | 1061624-72-3

• 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: N'-{3-(R)-[2-(S)-(1H-indol-3-yl)-1-(methylcarbamoyl)-ethylcarbamoyl]-5-methylhexanoyl}-N-4-(4-bromophenyl)benzenesulfonylhydrazide
• 英文别名: (2R)-2-[2-[2-[4-(4-bromophenyl)phenyl]sulfonylhydrazinyl]-2-oxoethyl]-N-[(2S)-3-(1H-indol-3-yl)-1-(methylamino)-1-oxopropan-2-yl]-4-methylpentanamide
• CAS: 1061624-72-3
• 化学式: C₃₂H₃₆BrN₅O₅S
• 分子量: 682.638
• InChiKey: ODFXJYBYTABKHA-BTYSJIOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  158
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-(4-溴苯基)苯磺酰氯 、 N''-{3-(R)-[2-(S)-(1H-indol-3-yl)-1-(methylcarbamoyl)-ethylcarbamoyl]-5-methylhexanoyl}-hydrazide 在 吡啶 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 18.0h， 以70%的产率得到N'-{3-(R)-[2-(S)-(1H-indol-3-yl)-1-(methylcarbamoyl)-ethylcarbamoyl]-5-methylhexanoyl}-N-4-(4-bromophenyl)benzenesulfonylhydrazide
  参考文献：
  名称：

  Introduction of the 4-(4-bromophenyl)benzenesulfonyl group to hydrazide analogs of Ilomastat leads to potent gelatinase B (MMP-9) inhibitors with improved selectivity

  摘要：

  Hydrazide derivatives of Ilomastat, carrying either aryl groups or distinct alkyl and arylsulfonyl moieties were synthesized and evaluated for their MMP inhibitory activity. Potent and selective MMP-9 inhibition (IC50 = 3 nM) was observed for compound 3m (arylsulfonyl group: 4-(4-Br-C6H4)-C6H4-SO2-). Interaction with the S-2 enzyme subsite is mainly responsible for the inhibitory properties of this derivative as confirmed by molecular docking computation. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.041

文献信息

• PARKIN LIGASE ACTIVATION METHODS AND COMPOSITIONS
  申请人：An2H Discovery Limited

  公开号：US20160160205A1

  公开（公告）日：2016-06-09

  The present invention is directed to methods and compositions for activating a Parkin ligase by administering to a subject in need thereof a therapeutically effective amount of a compound that disrupts at least one Parkin ligase zinc finger. The present invention is also directed to methods of treating and/or reducing the incidence of diseases or conditions related to the activation of Parkin ligase.
• Introduction of the 4-(4-bromophenyl)benzenesulfonyl group to hydrazide analogs of Ilomastat leads to potent gelatinase B (MMP-9) inhibitors with improved selectivity
  作者：Gwennaël LeDour、Gautier Moroy、Matthieu Rouffet、Erika Bourguet、Dominique Guillaume、Martine Decarme、Haquima ElMourabit、Franck Augé、Alain J.P. Alix、Jean-Yves Laronze、Georges Bellon、William Hornebeck、Janos Sapi

  DOI：10.1016/j.bmc.2008.07.041

  日期：2008.9

  Hydrazide derivatives of Ilomastat, carrying either aryl groups or distinct alkyl and arylsulfonyl moieties were synthesized and evaluated for their MMP inhibitory activity. Potent and selective MMP-9 inhibition (IC50 = 3 nM) was observed for compound 3m (arylsulfonyl group: 4-(4-Br-C6H4)-C6H4-SO2-). Interaction with the S-2 enzyme subsite is mainly responsible for the inhibitory properties of this derivative as confirmed by molecular docking computation. (C) 2008 Elsevier Ltd. All rights reserved.