苯磺酰胺,4-[2-[[(苯基氨基)羰基]氨基]乙基]- | 10080-04-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 苯磺酰胺,4-[2-[[(苯基氨基)羰基]氨基]乙基]-
• 英文名称: 3-phenyl-1-[2-(4-sulfamoylphenyl)ethyl]urea
• 英文别名: 4-(2-(3-phenylureido)ethyl)benzenesulfonamide；1-Phenyl-3-(2-(4-sulfamoylphenyl)ethyl)urea；1-phenyl-3-[2-(4-sulfamoylphenyl)ethyl]urea
• CAS: 10080-04-3
• 化学式: C₁₅H₁₇N₃O₃S
• 分子量: 319.384
• InChiKey: CQMWNAHSFVPGJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  101.29
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  苯磺酰胺,4-[2-[[(苯基氨基)羰基]氨基]乙基]- 、 N-cyano-N'-cyclohexyl-S-methylcarbamimidothioate 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 以37%的产率得到
  参考文献：
  名称：

  4-取代苯磺酰基氰基胍的首次合成

  摘要：

  N′-取代的-N-氰基-S-甲基氨基甲酰胺基硫酸酯与4-取代的苯磺酰胺反应，得到相应的磺酰基氰基胍。

  DOI：

  10.1016/0040-4039(96)01663-2
• 作为产物：
  描述：

  异氰酸苯酯 、 4-(2-氨乙基)苯磺酰胺 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 苯磺酰胺,4-[2-[[(苯基氨基)羰基]氨基]乙基]-
  参考文献：
  名称：

  Carbonic anhydrase inhibitors - Part 49: Synthesis of substituted ureido and thioureido derivatives of aromatic/heterocyclic sulfonamides with increased affinities for isozyme I

  摘要：

  Reaction of nine aromatic/heterocyclic sulfonamides containing a free amino group with aryl isocyanates/isothiocyanates or allyl isothiocyanate afforded the corresponding urea/thiourea derivatives, which were characterized by standard physico-chemical procedures and assayed as inhibitors of three isozymes of carbonic anhydrase (CA), i.e. hCA I, hCA II and bCA IV (h = human, b = bovine isozyme). Another series of compounds, 1,5-disubstituted-2-thiobiuret derivatives, were prepared by reaction of 3,4-dichlorophenyl isocyanate with thioureido-containing aromatic/heterocyclic sulfonamides. Good inhibition of all these three CA isozymes was observed with the new compounds, but an exciting finding was that the ureas/thioureas and especially the above-mentioned thiobiurets reported here have an increased affinity to the slow isozyme hCA I, generally less susceptible to inhibition by sulfonamides, as compared to the rapid isozymes hCA II and bCA IV. Some of the new compounds might constitute good lead molecules for developing more selective CA I inhibitors. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80033-0

文献信息

• Carbonic anhydrase inhibitors - Part 49: Synthesis of substituted ureido and thioureido derivatives of aromatic/heterocyclic sulfonamides with increased affinities for isozyme I
  作者：Claudiu T. Supuran、Andrea Scozzafava、Bogdan C. Jurca、Marc A. Ilies

  DOI：10.1016/s0223-5234(98)80033-0

  日期：1998.2

  Reaction of nine aromatic/heterocyclic sulfonamides containing a free amino group with aryl isocyanates/isothiocyanates or allyl isothiocyanate afforded the corresponding urea/thiourea derivatives, which were characterized by standard physico-chemical procedures and assayed as inhibitors of three isozymes of carbonic anhydrase (CA), i.e. hCA I, hCA II and bCA IV (h = human, b = bovine isozyme). Another series of compounds, 1,5-disubstituted-2-thiobiuret derivatives, were prepared by reaction of 3,4-dichlorophenyl isocyanate with thioureido-containing aromatic/heterocyclic sulfonamides. Good inhibition of all these three CA isozymes was observed with the new compounds, but an exciting finding was that the ureas/thioureas and especially the above-mentioned thiobiurets reported here have an increased affinity to the slow isozyme hCA I, generally less susceptible to inhibition by sulfonamides, as compared to the rapid isozymes hCA II and bCA IV. Some of the new compounds might constitute good lead molecules for developing more selective CA I inhibitors. (C) Elsevier, Paris.
• First synthesis of 4-substituted benzenesulfonylcyanoguanidines
  作者：Bernard Masereel、Philippe Lebrun、Jean Michel Dogné、Pascal de Tullio、Bernard Pirotte、Lionel Pochet、Ousman Diouf、Jacques Delarge

  DOI：10.1016/0040-4039(96)01663-2

  日期：1996.9

  N'-substituted-N-cyano-S-methylcarbamimidothioates react with 4-substitutedbenzene sulfonamides to give the corresponding sulfonylcyanoguanidines.

  N′-取代的-N-氰基-S-甲基氨基甲酰胺基硫酸酯与4-取代的苯磺酰胺反应，得到相应的磺酰基氰基胍。