4-methyl-7-nitro-4H-1,2,4-benzothiadiazine 1,1-dioxide | 945388-22-7

• 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: 4-methyl-7-nitro-4H-1,2,4-benzothiadiazine 1,1-dioxide
• 英文别名: 4-Methyl-7-nitro-1lambda6,2,4-benzothiadiazine 1,1-dioxide；4-methyl-7-nitro-1λ6,2,4-benzothiadiazine 1,1-dioxide
• CAS: 945388-22-7
• 化学式: C₈H₇N₃O₄S
• 分子量: 241.227
• InChiKey: CNDRCKCUFSULDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-methyl-7-nitro-4H-1,2,4-benzothiadiazine 1,1-dioxide 在 palladium on activated charcoal sodium tetrahydroborate 、 氢气 作用下， 以 乙醇 、 异丙醇 为溶剂， 20.0 ℃ 、500.01 kPa 条件下， 反应 4.25h， 生成 4-Methyl-1,1-dioxo-2,3-dihydro-1lambda6,2,4-benzothiadiazin-7-amine
  参考文献：
  名称：

  Design, Synthesis, and Pharmacology of Novel 7-Substituted 3,4-Dihydro-2H-1,2,4-benzothiadiazine 1,1-Dioxides as Positive Allosteric Modulators of AMPA Receptors

  摘要：

  A series of 3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxides have been synthesized and evaluated as potentiators of AMPA receptors. Attention was paid to the impact of the substituent introduced at the 7-position of the heterocycle. The biological evaluation was achieved by measuring the AMPA current in rat cortex mRNA-injected Xenopus oocytes. The most potent compound, 4-ethyl-7-fluoro-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide (12a) was found to be active in an object recognition test in rats demonstrating cognition enhancing effects in vivo after oral administration.

  DOI：

  10.1021/jm070120i
• 作为产物：
  描述：

  7-硝基-4H-苯并[e][1,2,4]噻二嗪1,1-二氧化物 、 碘甲烷 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以70%的产率得到4-methyl-7-nitro-4H-1,2,4-benzothiadiazine 1,1-dioxide
  参考文献：
  名称：

  Design, Synthesis, and Pharmacology of Novel 7-Substituted 3,4-Dihydro-2H-1,2,4-benzothiadiazine 1,1-Dioxides as Positive Allosteric Modulators of AMPA Receptors

  摘要：

  A series of 3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxides have been synthesized and evaluated as potentiators of AMPA receptors. Attention was paid to the impact of the substituent introduced at the 7-position of the heterocycle. The biological evaluation was achieved by measuring the AMPA current in rat cortex mRNA-injected Xenopus oocytes. The most potent compound, 4-ethyl-7-fluoro-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide (12a) was found to be active in an object recognition test in rats demonstrating cognition enhancing effects in vivo after oral administration.

  DOI：

  10.1021/jm070120i