4-sulphonamidobenzoic acid 4-(nitrooxymethyl)benzyl ester | 1033596-75-6

• 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: 4-sulphonamidobenzoic acid 4-(nitrooxymethyl)benzyl ester
• 英文别名: 4-(Nitrooxymethyl)benzyl-4-sulfamoylbenzoate；[4-(nitrooxymethyl)phenyl]methyl 4-sulfamoylbenzoate
• CAS: 1033596-75-6
• 化学式: C₁₅H₁₄N₂O₇S
• 分子量: 366.351
• InChiKey: MCDXWABKFCECMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  150
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-sulphonamidobenzoic acid 4-(chloromethyl)-benzyl ester 在 silver nitrate 作用下， 以 乙腈 为溶剂， 生成 4-sulphonamidobenzoic acid 4-(nitrooxymethyl)benzyl ester
  参考文献：
  名称：

  Synthesis and crystallographic analysis of new sulfonamides incorporating NO-donating moieties with potent antiglaucoma action

  摘要：

  Several aromatic/heterocyclic sulfonamide scaffolds have been used to synthesize compounds incorporating NO-donating moieties of the nitrate ester type, which have been investigated for the inhibition of five physiologically relevant human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms: hCA I (offtarget), II, IV and XII (antiglaucoma targets) and IX (antitumor target). Some of the new compounds showed effective in vitro inhibition of the target isoforms involved in glaucoma, and the X-ray crystal structure of one of them revealed factors associated with the marked inhibitory activity. In an animal model of ocular hypertension, one of the new compounds was twice more effective than dorzolamide in reducing elevated intraocular pressure characteristic of this disease, anticipating their potential for the treatment of glaucoma. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.046

文献信息

• WO2008/71421
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and crystallographic analysis of new sulfonamides incorporating NO-donating moieties with potent antiglaucoma action
  作者：Francesco Mincione、Francesca Benedini、Stefano Biondi、Alessandro Cecchi、Claudia Temperini、Giuseppe Formicola、Ilaria Pacileo、Andrea Scozzafava、Emanuela Masini、Claudiu T. Supuran

  DOI：10.1016/j.bmcl.2011.04.046

  日期：2011.6

  Several aromatic/heterocyclic sulfonamide scaffolds have been used to synthesize compounds incorporating NO-donating moieties of the nitrate ester type, which have been investigated for the inhibition of five physiologically relevant human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms: hCA I (offtarget), II, IV and XII (antiglaucoma targets) and IX (antitumor target). Some of the new compounds showed effective in vitro inhibition of the target isoforms involved in glaucoma, and the X-ray crystal structure of one of them revealed factors associated with the marked inhibitory activity. In an animal model of ocular hypertension, one of the new compounds was twice more effective than dorzolamide in reducing elevated intraocular pressure characteristic of this disease, anticipating their potential for the treatment of glaucoma. (C) 2011 Elsevier Ltd. All rights reserved.