Methyl 4-ethyl-1,1-dioxo-2,3-dihydro-1lambda6,2,4-benzothiadiazine-7-carboxylate | 945388-13-6

• 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: Methyl 4-ethyl-1,1-dioxo-2,3-dihydro-1lambda6,2,4-benzothiadiazine-7-carboxylate
• 英文别名: methyl 4-ethyl-1,1-dioxo-2,3-dihydro-1λ6,2,4-benzothiadiazine-7-carboxylate
• CAS: 945388-13-6
• 化学式: C₁₁H₁₄N₂O₄S
• 分子量: 270.309
• InChiKey: GTBMTDCIXBUBOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  84.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 4-ethyl-1,1-dioxo-2,3-dihydro-1lambda6,2,4-benzothiadiazine-7-carboxylate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以59%的产率得到4-Ethyl-1,1-dioxo-2,3-dihydro-1lambda6,2,4-benzothiadiazine-7-carboxylic acid
  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：

  methyl 4H-1,2,4-benzothiadiazine-7-carboxylate 1,1-dioxide 在 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 异丙醇 、 乙腈 为溶剂， 反应 3.75h， 生成 Methyl 4-ethyl-1,1-dioxo-2,3-dihydro-1lambda6,2,4-benzothiadiazine-7-carboxylate
  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

文献信息

• Design, Synthesis, and Pharmacology of Novel 7-Substituted 3,4-Dihydro-2<i>H</i>-1,2,4-benzothiadiazine 1,1-Dioxides as Positive Allosteric Modulators of AMPA Receptors
  作者：Pierre Francotte、Pascal de Tullio、Eric Goffin、Gaëlle Dintilhac、Emmanuel Graindorge、Pierre Fraikin、Pierre Lestage、Laurence Danober、Jean-Yves Thomas、Daniel-Henri Caignard、Bernard Pirotte

  DOI：10.1021/jm070120i

  日期：2007.6.1

  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.