6-chloro-7-fluoro-3-(1H-imidazol-1-yl)-4H-1,2,4-benzothiadiazine 1,1-dioxide | 863099-69-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻二嗪
• 英文名称: 6-chloro-7-fluoro-3-(1H-imidazol-1-yl)-4H-1,2,4-benzothiadiazine 1,1-dioxide
• 英文别名: 6-chloro-7-fluoro-3-imidazol-1-yl-4H-1lambda6,2,4-benzothiadiazine 1,1-dioxide；6-chloro-7-fluoro-3-imidazol-1-yl-4H-1λ6,2,4-benzothiadiazine 1,1-dioxide
• CAS: 863099-69-8
• 化学式: C₁₀H₆ClFN₄O₂S
• 分子量: 300.701
• InChiKey: BIJUYNGGFZTINJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-chloro-7-fluoro-3-(1H-imidazol-1-yl)-4H-1,2,4-benzothiadiazine 1,1-dioxide 、 环丁基胺 以 1,4-二氧六环 为溶剂， 反应 8.0h， 以55%的产率得到6-chloro-N-cyclobutyl-7-fluoro-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-氯-4-氟苯胺 在 氯磺酸 、 ammonium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 生成 6-chloro-7-fluoro-3-(1H-imidazol-1-yl)-4H-1,2,4-benzothiadiazine 1,1-dioxide
  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.