6-cyano-2-methyl-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxide | 80357-16-0

• 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-cyano-2-methyl-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxide
• 英文别名: 2-methyl-1,1,3-trioxo-4H-1lambda6,2,4-benzothiadiazine-6-carbonitrile；2-methyl-1,1,3-trioxo-4H-1λ6,2,4-benzothiadiazine-6-carbonitrile
• CAS: 80357-16-0
• 化学式: C₉H₇N₃O₃S
• 分子量: 237.239
• InChiKey: KXZWKWNRDRCKKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  98.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-cyano-2-methyl-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxide 在 platinum(IV) oxide 氢气 作用下， 以 乙醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以53%的产率得到6-(aminomethyl)-2-methyl-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxide hydrochloride
  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：

  氰化亚铜 、 6-bromo-2-methyl-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxide 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以76%的产率得到6-cyano-2-methyl-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-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

文献信息

• 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：——
• 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.