N-isobutyl-N'-(2-amino-4,5-difluorobenzenesulfonyl)thiourea | 863099-82-5

• 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: N-isobutyl-N'-(2-amino-4,5-difluorobenzenesulfonyl)thiourea
• 英文别名: 1-(2-Amino-4,5-difluorophenyl)sulfonyl-3-(2-methylpropyl)thiourea
• CAS: 863099-82-5
• 化学式: C₁₁H₁₅F₂N₃O₂S₂
• 分子量: 323.388
• InChiKey: QJZQRUPKZVDSPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-isobutyl-N'-(2-amino-4,5-difluorobenzenesulfonyl)thiourea 在 光气 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.0h， 生成 6,7-difluoro-N-(2-methylpropyl)-1,1-dioxo-4H-1lambda6,2,4-benzothiadiazin-3-imine
  参考文献：
  名称：

  3-Alkylamino-4H-1,2,4-benzothiadiazine 1,1-Dioxides as ATP-Sensitive Potassium Channel Openers:  Effect of 6,7-Disubstitution on Potency and Tissue Selectivity

  摘要：

  A series of 6,7-disubstituted 4H-1,2,4-benzothiadiazine 1,1-dioxides bearing a short alkylamino side chain in the 3-position were synthesized. These compounds were tested on rat pancreatic islets and on rat aorta rings. In vitro data indicated that in most cases substitution in the 6 and the 7 positions increased their activity as inhibitors of insulin secretion, while the myorelaxant potency of the drugs was maintained or enhanced according to the nature of the substituent in the 7-position. The presence of either chlorine or bromine atoms in the 6 and 7 positions did not improve the apparent selectivity of the drugs for the pancreatic tissue. By contrast, the introduction of one or two fluorine atoms, as well as the presence of a methoxy group in the 7-position, generated potent and selective inhibitors of insulin release. Radioisotopic and fluorimetric experiments performed with the most potent compound inhibiting insulin release (34, BPDZ 259, 6-chloro-7-fluoro-3-isopropylamino-4H-1,2,4-benzothiadiazine 1,1-dioxide) confirmed that the drug activated K-ATP channels. 34 was found to be one of the most potent and selective pancreatic potassium channel openers yet described.

  DOI：

  10.1021/jm0580050
• 作为产物：
  描述：

  3,4-二氟苯胺 在 氯磺酸 、 ammonium hydroxide 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 丙酮 为溶剂， 反应 7.5h， 生成 N-isobutyl-N'-(2-amino-4,5-difluorobenzenesulfonyl)thiourea
  参考文献：
  名称：

  3-Alkylamino-4H-1,2,4-benzothiadiazine 1,1-Dioxides as ATP-Sensitive Potassium Channel Openers:  Effect of 6,7-Disubstitution on Potency and Tissue Selectivity

  摘要：

  A series of 6,7-disubstituted 4H-1,2,4-benzothiadiazine 1,1-dioxides bearing a short alkylamino side chain in the 3-position were synthesized. These compounds were tested on rat pancreatic islets and on rat aorta rings. In vitro data indicated that in most cases substitution in the 6 and the 7 positions increased their activity as inhibitors of insulin secretion, while the myorelaxant potency of the drugs was maintained or enhanced according to the nature of the substituent in the 7-position. The presence of either chlorine or bromine atoms in the 6 and 7 positions did not improve the apparent selectivity of the drugs for the pancreatic tissue. By contrast, the introduction of one or two fluorine atoms, as well as the presence of a methoxy group in the 7-position, generated potent and selective inhibitors of insulin release. Radioisotopic and fluorimetric experiments performed with the most potent compound inhibiting insulin release (34, BPDZ 259, 6-chloro-7-fluoro-3-isopropylamino-4H-1,2,4-benzothiadiazine 1,1-dioxide) confirmed that the drug activated K-ATP channels. 34 was found to be one of the most potent and selective pancreatic potassium channel openers yet described.

  DOI：

  10.1021/jm0580050

文献信息

• 3-Alkylamino-4<i>H</i>-1,2,4-benzothiadiazine 1,1-Dioxides as ATP-Sensitive Potassium Channel Openers:  Effect of 6,7-Disubstitution on Potency and Tissue Selectivity
  作者：Pascal de Tullio、Stéphane Boverie、Bénédicte Becker、Marie-Hélène Antoine、Quynh-Anh Nguyen、Pierre Francotte、Stéphane Counerotte、Sophie Sebille、Bernard Pirotte、Philippe Lebrun

  DOI：10.1021/jm0580050

  日期：2005.7.1

  A series of 6,7-disubstituted 4H-1,2,4-benzothiadiazine 1,1-dioxides bearing a short alkylamino side chain in the 3-position were synthesized. These compounds were tested on rat pancreatic islets and on rat aorta rings. In vitro data indicated that in most cases substitution in the 6 and the 7 positions increased their activity as inhibitors of insulin secretion, while the myorelaxant potency of the drugs was maintained or enhanced according to the nature of the substituent in the 7-position. The presence of either chlorine or bromine atoms in the 6 and 7 positions did not improve the apparent selectivity of the drugs for the pancreatic tissue. By contrast, the introduction of one or two fluorine atoms, as well as the presence of a methoxy group in the 7-position, generated potent and selective inhibitors of insulin release. Radioisotopic and fluorimetric experiments performed with the most potent compound inhibiting insulin release (34, BPDZ 259, 6-chloro-7-fluoro-3-isopropylamino-4H-1,2,4-benzothiadiazine 1,1-dioxide) confirmed that the drug activated K-ATP channels. 34 was found to be one of the most potent and selective pancreatic potassium channel openers yet described.