7-硝基-4H-苯并[e][1,2,4]噻二嗪1,1-二氧化物 | 37162-50-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻二嗪
• 中文名称: 7-硝基-4H-苯并[e][1,2,4]噻二嗪1,1-二氧化物
• 英文名称: 7-nitro-4H-1,2,4-benzothiadiazine 1,1-dioxide
• 英文别名: 7-nitro-4H-benzo[e][1,2,4]thiadiazine-1,1-dione；7-Nitro-1,2,4-benzothiadiazin-1,1-dioxid；7-nitro-4H-benzo[e][1,2,4]thiadiazine 1,1-dioxide；7-Nitro-4H-benzo[e][1,2,4]thiadiazine 1,1-dioxide；7-nitro-4H-1λ6,2,4-benzothiadiazine 1,1-dioxide
• CAS: 37162-50-8
• 化学式: C₇H₅N₃O₄S
• 分子量: 227.2
• InChiKey: VXGQNQVXNSZYGA-UHFFFAOYSA-N

物化性质

• 熔点：
  265-266 °C
• 沸点：
  469.3±47.0 °C(Predicted)
• 密度：
  1.84±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 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：
  113
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  7-硝基-4H-苯并[e][1,2,4]噻二嗪1,1-二氧化物 在 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 异丙醇 、 乙腈 为溶剂， 反应 3.75h， 生成 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
• 作为产物：
  描述：

  2-氯-5-硝基苯磺酰胺 在 ammonium hydroxide 、 碳酸氢铵 、 copper(II) sulfate 作用下， 反应 4.0h， 生成 7-硝基-4H-苯并[e][1,2,4]噻二嗪1,1-二氧化物
  参考文献：
  名称：

  CN115572282

  摘要：

  公开号：

文献信息

• New Fluorinated 1,2,4-Benzothiadiazine 1,1-Dioxides: Discovery of an Orally Active Cognitive Enhancer Acting through Potentiation of the 2-Amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic Acid Receptors
  作者：Pierre Francotte、Eric Goffin、Pierre Fraikin、Pierre Lestage、Jean-Claude Van Heugen、Florian Gillotin、Laurence Danober、Jean-Yves Thomas、Patrice Chiap、Daniel-Henri Caignard、Bernard Pirotte、Pascal de Tullio

  DOI：10.1021/jm901495t

  日期：2010.2.25

  In the search of a potent cognitive enhancer, a series of 3,4-dihydro-2H-1,2,4-benzothiadiazine 1, 1-dioxides have been synthesized and evaluated its positive allosteric modulators of the AMPA receptors. In the present work, we focused our efforts on the insertion of mono- or polyfluoro-substituted alkyl chains at the 4-position of the thiadiazine ring In all attempt to enhance the pharmacokinetic behavior of previously described compounds. Among all the described compounds, 7-chloro-4-(2-fluoroethyl)-3,4-dihydro-2H-1,2,4-benzothiadiazine 1, 1-dioxide, 12b, was shown to exert a strong activity on AMPA receptors in vitro and it marked cognitive-enhancing effect in vivo after oral administration to Wistar rats. Considering its in vivo activity, the metabolic degradation of 12b was studied and compared to that of its nonfluorinated analogue 9b. Taken together, results of this study clearly validated the positive impact of the fluorine atom on the alkyl chain at file 4-position of benzothiadiazine dioxides oil activity and metabolic stability.
• 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.
• CN115572282
  申请人：——

  公开号：——

  公开（公告）日：——