[2-methoxy-4-[3-(4-nitrooxybutoxy)-3-oxoprop-1-enyl]phenyl] 3-[(5-sulfamoyl-1,3,4-thiadiazol-2-yl)sulfamoyl]benzoate | 1033598-36-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: [2-methoxy-4-[3-(4-nitrooxybutoxy)-3-oxoprop-1-enyl]phenyl] 3-[(5-sulfamoyl-1,3,4-thiadiazol-2-yl)sulfamoyl]benzoate
• CAS: 1033598-36-5
• 化学式: C₂₃H₂₃N₅O₁₂S₃
• 分子量: 657.66
• InChiKey: JMUJIEXVYMRWPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.76
• 重原子数：
  43.0
• 可旋转键数：
  15.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  246.31
• 氢给体数：
  2.0
• 氢受体数：
  15.0

反应信息

• 作为产物：
  描述：

  3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid 4-(nitrooxy)butyl ester 、 3-(5-Sulfamoyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-benzoic acid 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 [2-methoxy-4-[3-(4-nitrooxybutoxy)-3-oxoprop-1-enyl]phenyl] 3-[(5-sulfamoyl-1,3,4-thiadiazol-2-yl)sulfamoyl]benzoate
  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

• 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.