4-(3-phenylsulfonylfuroxan-4-yloxy)benzenesulfonamide | 1380783-55-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(3-phenylsulfonylfuroxan-4-yloxy)benzenesulfonamide
• 英文别名: 4-[[4-(Benzenesulfonyl)-5-oxido-1,2,5-oxadiazol-5-ium-3-yl]oxy]benzenesulfonamide；4-[[4-(benzenesulfonyl)-5-oxido-1,2,5-oxadiazol-5-ium-3-yl]oxy]benzenesulfonamide
• CAS: 1380783-55-0
• 化学式: C₁₄H₁₁N₃O₇S₂
• 分子量: 397.389
• InChiKey: WERYFCMHCDFDSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  172
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-(3-phenylsulfonylfuroxan-4-yloxy)benzenesulfonamide 、 异氰酸正丁酯 在 copper(l) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以15%的产率得到1-[4-[[4-(Benzenesulfonyl)-5-oxido-1,2,5-oxadiazol-5-ium-3-yl]oxy]phenyl]sulfonyl-3-butylurea
  参考文献：
  名称：

  Synthesis and preliminary biological profile of new NO-donor tolbutamide analogues

  摘要：

  We describe a new class of NO-donor hypoglycemic products obtained by joining tolbutamide, a typical hypoglycemic sulfonylurea, with a NO-donor moiety through a hard link. As NO-donors we chose either furoxan (1,2,5-oxadiazole 2-oxide) derivatives or the classical nitrooxy function. A preliminary biological characterization of these compounds, including stimulation of insulin release from cultured rat pancreatic beta-cells and in vitro vasodilator and anti-aggregatory activities, is reported. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.103
• 作为产物：
  描述：

  4-羟基苯磺酰胺 、 呋咱氮氧化物供体 在 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以29%的产率得到4-(3-phenylsulfonylfuroxan-4-yloxy)benzenesulfonamide
  参考文献：
  名称：

  Furazan and furoxan sulfonamides are strong α-carbonic anhydrase inhibitors and potential antiglaucoma agents

  摘要：

  A series of furazan and furoxan sulfonamides were prepared and studied for their ability to inhibit human carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA I, hCA II, hCA IX, and hCA XII. The simple methyl substituted products 3-5 were potent inhibitors. Differing structural modifications of these leads had differing effects on potency and selectivity. In particular, products in which the sulfonamide group is separated from the hetero ring by a phenylene bridge retained high potency only on the hCA XII isoform. The sulfonamides 3-5 exerted intraocular pressure (IOP) lowering effects in vivo in hypertensive rabbits more efficiently than dorzolamide. Some other products (39-42), although less effective in vitro hCA II/XII inhibitors, also effectively lowered IOP in two different animal models of glaucoma. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.06.016

文献信息

• Synthesis and preliminary biological profile of new NO-donor tolbutamide analogues
  作者：Yasinalli Tamboli、Loretta Lazzarato、Elisabetta Marini、Stefano Guglielmo、Michela Novelli、Pascale Beffy、Pellegrino Masiello、Roberta Fruttero、Alberto Gasco

  DOI：10.1016/j.bmcl.2012.03.103

  日期：2012.6

  We describe a new class of NO-donor hypoglycemic products obtained by joining tolbutamide, a typical hypoglycemic sulfonylurea, with a NO-donor moiety through a hard link. As NO-donors we chose either furoxan (1,2,5-oxadiazole 2-oxide) derivatives or the classical nitrooxy function. A preliminary biological characterization of these compounds, including stimulation of insulin release from cultured rat pancreatic beta-cells and in vitro vasodilator and anti-aggregatory activities, is reported. (C) 2012 Elsevier Ltd. All rights reserved.
• Furazan and furoxan sulfonamides are strong α-carbonic anhydrase inhibitors and potential antiglaucoma agents
  作者：Konstantin Chegaev、Loretta Lazzarato、Yasinalli Tamboli、Donatella Boschi、Marco Blangetti、Andrea Scozzafava、Fabrizio Carta、Emanuela Masini、Roberta Fruttero、Claudiu T. Supuran、Alberto Gasco

  DOI：10.1016/j.bmc.2014.06.016

  日期：2014.8

  A series of furazan and furoxan sulfonamides were prepared and studied for their ability to inhibit human carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA I, hCA II, hCA IX, and hCA XII. The simple methyl substituted products 3-5 were potent inhibitors. Differing structural modifications of these leads had differing effects on potency and selectivity. In particular, products in which the sulfonamide group is separated from the hetero ring by a phenylene bridge retained high potency only on the hCA XII isoform. The sulfonamides 3-5 exerted intraocular pressure (IOP) lowering effects in vivo in hypertensive rabbits more efficiently than dorzolamide. Some other products (39-42), although less effective in vitro hCA II/XII inhibitors, also effectively lowered IOP in two different animal models of glaucoma. (C) 2014 Elsevier Ltd. All rights reserved.