5-nitrooxypentanoic acid 4-aminosulfonylphenyl ester | 1033598-78-5

• 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: 5-nitrooxypentanoic acid 4-aminosulfonylphenyl ester
• 英文别名: (4-Sulfamoylphenyl) 5-nitrooxypentanoate
• CAS: 1033598-78-5
• 化学式: C₁₁H₁₄N₂O₇S
• 分子量: 318.307
• InChiKey: SEAGRXMKNLZORR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  5-bromopentanoic acid 4-aminosulfonylphenyl ester 在 silver nitrate 作用下， 以 乙腈 为溶剂， 生成 5-nitrooxypentanoic acid 4-aminosulfonylphenyl 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：——
• [EN] NITRATE ESTERS OF CARBONIC ANHYDRASE INHIBITORS<br/>[FR] ESTERS DE L'ACIDE NITRIQUE DES INHIBITEURS D'ANHYDRASE CARBONIQUE
  申请人：NICOX SA

  公开号：WO2008071421A1

  公开（公告）日：2008-06-19

  [EN] Nitroderivatives of carbonic anhydrase inhibitors having improved pharmacological activity and enhanced tolerability are described. They can be employed for the treatment of glaucoma, ocular hypertension, age-related macular degeneration, diabetic macular edema, diabetic retinopathy, hypertensive retinopathy and retinal vasculopathies, cancer, epilepsy, high-altitude disorders and neuromuscular diseases.
  [FR] L'invention concerne des dérivés nitrés d'inhibiteurs d'anhydrase carbonique présentant une activité pharmacologique et une tolérabilité améliorées. Ces dérivés peuvent être utilisés pour le traitement du glaucome, de l'hypertension oculaire, de la dégénérescence maculaire liée à l'âge, de l' dème maculaire diabétique, de la rétinopathie diabétique, de la rétinopathie et des vasculopathies rétiniennes hypertensives, du cancer, de l'épilepsie, des troubles liés à l'altitude et des maladies neuromusculaires.
• 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.