N-(2-Diethylamino-ethyl)-4-(5-sulfamoyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-benzamide

• 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-(2-Diethylamino-ethyl)-4-(5-sulfamoyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-benzamide
• 英文别名: N-[2-(diethylamino)ethyl]-4-[(5-sulfamoyl-1,3,4-thiadiazol-2-yl)sulfamoyl]benzamide
• 化学式: C₁₅H₂₂N₆O₅S₃
• 分子量: 462.575
• InChiKey: NZUFHNXGURICPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  209
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  4-(5-sulfamoyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-benzoic acid 在 氯化亚砜 作用下， 以 乙腈 、 苯 为溶剂， 生成 N-(2-Diethylamino-ethyl)-4-(5-sulfamoyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-benzamide
  参考文献：
  名称：

  Carbonic anhydrase inhibitors: Topically acting antiglaucoma sulfonamides incorporating esters and amides of 3- and 4-carboxybenzolamide

  摘要：

  Reaction of 3- and 4-carboxybenzenesulfonyl chloride with 5-amino-1,3,4-thiadiazole-2-sulfonaniide/5-imino-4-methyl-delta(2)-1,3,4-thiadiazoline-2-sulfonamide afforded two series of benzolamide analogues to which the carboxyl moiety has been derivatized as esters or amides. in order to reduce their very polar character. The new derivatives showed low nanomolar affinity for three carbonic anhydrase (CA) isozymes, CA I, II and IV, and were effective as topical antiglaucoma agents in normotensive rabbits. Efficacy of several of the new sulfonamides reported was better than that of the standard drugs dorzolamide and brinzolamide, whereas their duration of action was prolonged as compared to that of the clinically used drugs. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00580-8

文献信息

• Carbonic anhydrase inhibitors: Topically acting antiglaucoma sulfonamides incorporating esters and amides of 3- and 4-carboxybenzolamide
  作者：Angela Casini、Andrea Scozzafava、Francesco Mincione、Luca Menabuoni、Michele Starnotti、Claudiu T Supuran

  DOI：10.1016/s0960-894x(03)00580-8

  日期：2003.9

  Reaction of 3- and 4-carboxybenzenesulfonyl chloride with 5-amino-1,3,4-thiadiazole-2-sulfonaniide/5-imino-4-methyl-delta(2)-1,3,4-thiadiazoline-2-sulfonamide afforded two series of benzolamide analogues to which the carboxyl moiety has been derivatized as esters or amides. in order to reduce their very polar character. The new derivatives showed low nanomolar affinity for three carbonic anhydrase (CA) isozymes, CA I, II and IV, and were effective as topical antiglaucoma agents in normotensive rabbits. Efficacy of several of the new sulfonamides reported was better than that of the standard drugs dorzolamide and brinzolamide, whereas their duration of action was prolonged as compared to that of the clinically used drugs. (C) 2003 Elsevier Ltd. All rights reserved.