thiophene-2-carboxylic acid-(4-sulfamoyl-anilide) | 301301-95-1

• 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: thiophene-2-carboxylic acid-(4-sulfamoyl-anilide)
• 英文别名: Thiophen-2-carbonsaeure-(4-sulfamoyl-anilid)；N-(4-sulfamoylphenyl)thiophene-2-carboxamide
• CAS: 301301-95-1
• 化学式: C₁₁H₁₀N₂O₃S₂
• mdl: MFCD00596296
• 分子量: 282.344
• InChiKey: LXJKBJZVOISOOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  126
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-噻吩甲酰氯 、 磺胺 在 三乙胺 作用下， 以 乙腈 为溶剂， 生成 thiophene-2-carboxylic acid-(4-sulfamoyl-anilide)
  参考文献：
  名称：

  Carbonic anhydrase inhibitors: sulfonamides incorporating furan-, thiophene- and pyrrole-carboxamido groups possess strong topical intraocular pressure lowering properties as aqueous suspensions

  摘要：

  Important physiological and physio-pathological functions are played by several carbonic anhydrase (CAI EC 4.2.1.1) isozymes, which are strongly inhibited by aromatic and heterocyclic sulfonamides. Here we report several new types of such sulfonamides, incorporating furan-, thiophene- and pyrrole-carboxamide moieties in their molecules. Some of these compounds showed very good CA II and CA IV inhibitory properties, with affinities for the enzymes in the low nanomolar range. Due to their relatively low water solubility, some of the most active CA II inhibitors reported here have been formulated as aqueous suspension for topical administration as antiglaucoma agents, in normotensive and glaucomatous rabbits. The derivatives incorporating furan- and pyrrole-carboxamide moieties (but not the corresponding thiophene-substituted derivatives), showed effective and long-lasting intraocular pressure (IOP) lowering both in normotensive as well as glaucomatous animals, with potencies superior to dorzolamide and brinzolamide, the two available topically acting sulfonamide drugs. This is the first example of non-water soluble sulfonamides that significantly lower IOP, being thus similar with the recently introduced drug brinzolamide, which belongs to a completely different chemical family of antiglaucoma sulfonamides. (C) 2000 Elsevier Science Ltd, All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00143-7

文献信息

• Sulfanilamide Compounds. IV. N⁴-Aryl- and N⁴-Arylidine-N¹-substituted Sulfanilamides
  作者：H. G. Kolloff、James H. Hunter

  DOI：10.1021/ja01864a004

  日期：1940.7
• Carbonic anhydrase inhibitors: sulfonamides incorporating furan-, thiophene- and pyrrole-carboxamido groups possess strong topical intraocular pressure lowering properties as aqueous suspensions
  作者：Monica Ilies、Claudiu T. Supuran、Andrea Scozzafava、Angela Casini、Francesco Mincione、Luca Menabuoni、Miron T. Caproiu、Maria Maganu、Mircea D. Banciu

  DOI：10.1016/s0968-0896(00)00143-7

  日期：2000.8

  Important physiological and physio-pathological functions are played by several carbonic anhydrase (CAI EC 4.2.1.1) isozymes, which are strongly inhibited by aromatic and heterocyclic sulfonamides. Here we report several new types of such sulfonamides, incorporating furan-, thiophene- and pyrrole-carboxamide moieties in their molecules. Some of these compounds showed very good CA II and CA IV inhibitory properties, with affinities for the enzymes in the low nanomolar range. Due to their relatively low water solubility, some of the most active CA II inhibitors reported here have been formulated as aqueous suspension for topical administration as antiglaucoma agents, in normotensive and glaucomatous rabbits. The derivatives incorporating furan- and pyrrole-carboxamide moieties (but not the corresponding thiophene-substituted derivatives), showed effective and long-lasting intraocular pressure (IOP) lowering both in normotensive as well as glaucomatous animals, with potencies superior to dorzolamide and brinzolamide, the two available topically acting sulfonamide drugs. This is the first example of non-water soluble sulfonamides that significantly lower IOP, being thus similar with the recently introduced drug brinzolamide, which belongs to a completely different chemical family of antiglaucoma sulfonamides. (C) 2000 Elsevier Science Ltd, All rights reserved.