2-Amino-5-brom-4-chlor-benzol-sulfonsaeureamid | 59018-48-3

• 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: 2-Amino-5-brom-4-chlor-benzol-sulfonsaeureamid
• 英文别名: 2-Amino-5-bromo-4-chlorobenzenesulfonamide
• CAS: 59018-48-3
• 化学式: C₆H₆BrClN₂O₂S
• 分子量: 285.549
• InChiKey: VSONZHUQQSOJEN-UHFFFAOYSA-N

物化性质

• 熔点：
  177-180 °C
• 沸点：
  456.3±55.0 °C(Predicted)
• 密度：
  1.919±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Amino-5-brom-4-chlor-benzol-sulfonsaeureamid 以 1,4-二氧六环 为溶剂， 反应 10.0h， 生成 7-bromo-6-chloro-N-cyclobutyl-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：

  2-amino-5-bromo-4-chlorobenzenesulfonyl chloride 在 ammonium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 生成 2-Amino-5-brom-4-chlor-benzol-sulfonsaeureamid
  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

• Di Bella; Monzani; Albasini, Farmaco, Edizione Scientifica, 1966, vol. 21, # 2, p. 829 - 838
  作者：Di Bella、Monzani、Albasini、Conti

  DOI：——

  日期：——
• RAFFA; DIBELLA; MONZANI, Farmaco, Edizione Scientifica, 1964, vol. 19, p. 47 - 54
  作者：RAFFA、DIBELLA、MONZANI

  DOI：——

  日期：——