4-methyl-7-nitro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide | 62533-49-7

• 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-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide
• 英文别名: 4-Methyl-7-nitro-2,3-dihydro-1lambda6,2,4-benzothiadiazine 1,1-dioxide；4-methyl-7-nitro-2,3-dihydro-1λ6,2,4-benzothiadiazine 1,1-dioxide
• CAS: 62533-49-7
• 化学式: C₈H₉N₃O₄S
• 分子量: 243.243
• InChiKey: KXSDYOQJHJXWHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-methyl-7-nitro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 3.5h， 以55%的产率得到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：

  4-methyl-7-nitro-4H-1,2,4-benzothiadiazine 1,1-dioxide 在 sodium tetrahydroborate 作用下， 以 异丙醇 为溶剂， 反应 0.75h， 以78%的产率得到4-methyl-7-nitro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine 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

文献信息

• Intramolecular insertion of arylsulfonylnitrenes into aliphatic side chains
  作者：Rudolph A. Abramovitch、Therinadar Chellathurai、William D. Holcomb、Ian T. McMaster、Danny P. Vanderpool

  DOI：10.1021/jo00437a030

  日期：1977.8
• ABRAMOVITCH R. A.; CHELLATHURAI T.; HOLOCOMB W. D.; MCMASTER I. T.; VANDE+, J. ORG. CHEM. <JOCE-AH>, 1977, 42, NO 17, 2920-2926
  作者：ABRAMOVITCH R. A.、 CHELLATHURAI T.、 HOLOCOMB W. D.、 MCMASTER I. T.、 VANDE+

  DOI：——

  日期：——
• 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.