8-bromo-1,1-dioxo-1,4-dihydro-2H-1λ⁶-benzo[1,2,4]thiadiazin-3-one | 71254-66-5

• 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: 8-bromo-1,1-dioxo-1,4-dihydro-2H-1λ⁶-benzo[1,2,4]thiadiazin-3-one
• 英文别名: 8-bromo-1,1-diketo-4H-benzo[e][1,2,4]thiadiazin-3-one；8-bromo-1,1-dioxo-4H-1λ6,2,4-benzothiadiazin-3-one
• CAS: 71254-66-5
• 化学式: C₇H₅BrN₂O₃S
• 分子量: 277.098
• InChiKey: PPWKZACSDAJCDJ-UHFFFAOYSA-N

物化性质

• 熔点：
  290-300 °C(Solv: ethanol (64-17-5))
• 密度：
  1.877±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  溶剂黄146 、 8-bromo-1,1-dioxo-1,4-dihydro-2H-1λ⁶-benzo[1,2,4]thiadiazin-3-one 在 PPA 作用下， 反应 3.0h， 生成 8-bromo-3-methyl-4H-1,2,4-benzothiadiazine dioxide
  参考文献：
  名称：

  Aminomethyl-1,2,4-benzothiadiazines as potential analogs of .gamma.-aminobutyric acid. Unexpected discovery of a taurine antagonist

  摘要：

  A series of 6- and 8-(aminomethyl)-4H-1,2,4-benzothiadiazine 1,1-dioxides has been synthesized and tested for interaction with various GABA systems. None of the compounds showed significant GABA-mimetic properties, but unexpectedly, compound 7 [6-(aminomethyl)-3-methyl-4H-1,2,4-benzothiadiazine 1,1-dioxide] possessed the properties of a selective antagonist of taurine, as measured by the antagonism of taurine-induced inhibition of rat cerebellar Purkinje firing.

  DOI：

  10.1021/jm00344a004
• 作为产物：
  描述：

  氯磺酰异氰酸酯 、 间溴苯胺 生成 6-bromo-1,1-dioxo-1,4-dihydro-2H-1λ⁶-benzo[1,2,4]thiadiazin-3-one 、 8-bromo-1,1-dioxo-1,4-dihydro-2H-1λ⁶-benzo[1,2,4]thiadiazin-3-one
  参考文献：
  名称：

  Girard,Y. et al., Journal of the Chemical Society. Perkin transactions I, 1979, p. 1043 - 1047

  摘要：

  DOI：

文献信息

• GIRARD Y.; ATKINSON J. G.; ROKACH J., J. CHEM. SOC. PERKIN TRANS., PART 1, 1979, NO 4, 1043-1047
  作者：GIRARD Y.、 ATKINSON J. G.、 ROKACH J.

  DOI：——

  日期：——
• GIRARD, Y.;ATKINSON, J. G.;HAUBRICH, D. R.;WILLIAMS, M.;YARBROUGH, G. G., J. MED. CHEM., 1982, 25, N 2, 113-116
  作者：GIRARD, Y.、ATKINSON, J. G.、HAUBRICH, D. R.、WILLIAMS, M.、YARBROUGH, G. G.

  DOI：——

  日期：——
• Girard,Y. et al., Journal of the Chemical Society. Perkin transactions I, 1979, p. 1043 - 1047
  作者：Girard,Y. et al.

  DOI：——

  日期：——
• Aminomethyl-1,2,4-benzothiadiazines as potential analogs of .gamma.-aminobutyric acid. Unexpected discovery of a taurine antagonist
  作者：Yves Girard、Joseph G. Atkinson、Dean R. Haubrich、Michael Williams、George G. Yarbrough

  DOI：10.1021/jm00344a004

  日期：1982.2

  A series of 6- and 8-(aminomethyl)-4H-1,2,4-benzothiadiazine 1,1-dioxides has been synthesized and tested for interaction with various GABA systems. None of the compounds showed significant GABA-mimetic properties, but unexpectedly, compound 7 [6-(aminomethyl)-3-methyl-4H-1,2,4-benzothiadiazine 1,1-dioxide] possessed the properties of a selective antagonist of taurine, as measured by the antagonism of taurine-induced inhibition of rat cerebellar Purkinje firing.