3-(7-chloro-1,1-dioxide-3,4-dihydro-2H-1,2,4-benzothiadiazine-5-yl)aniline | 1349145-92-1

• 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: 3-(7-chloro-1,1-dioxide-3,4-dihydro-2H-1,2,4-benzothiadiazine-5-yl)aniline
• 英文别名: 3-(7-chloro-1,1-dioxo-3,4-dihydro-2H-1lambda6,2,4-benzothiadiazin-5-yl)aniline；3-(7-chloro-1,1-dioxo-3,4-dihydro-2H-1λ6,2,4-benzothiadiazin-5-yl)aniline
• CAS: 1349145-92-1
• 化学式: C₁₃H₁₂ClN₃O₂S
• 分子量: 309.776
• InChiKey: KOWVLKYYNGCAAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  92.6
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  7-chloro-5-iodo-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide 、 3-氨基苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 3.0h， 以51%的产率得到3-(7-chloro-1,1-dioxide-3,4-dihydro-2H-1,2,4-benzothiadiazine-5-yl)aniline
  参考文献：
  名称：

  5-Arylbenzothiadiazine Type Compounds as Positive Allosteric Modulators of AMPA/Kainate Receptors

  摘要：

  The potential therapeutic benefit of compounds able to activate AMPA receptors (AMPAr) has led to the search for new AMPAr positive modulators. On the basis of crystallographic data of the benzothiadiazines binding mode in the S1S2 GluA2 dimer interface, a set of 5-aryl-2,3-dihydrobenzothiadiazine type compounds has been synthesized and tested. Electrophysiological results suggested that 5-heteroaryl substituents on the benzothiadiazine core like 3-furanyl and 3-thiophenyl dramatically enhance the activity as positive modulators of AMPAr with respect to IDRA21 and cyclothiazide. Mouse brain microdialysis studies have suggested that 7-chloro-5-(3-furyl)-3-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide crosses the blood-brain barrier after intraperitoneal injection. Biological results have been rationalized by a computational docking simulation that it has currently employed to design new AMPAr-positive modulator candidates.

  DOI：

  10.1021/ml200184w

文献信息

• 5-Arylbenzothiadiazine Type Compounds as Positive Allosteric Modulators of AMPA/Kainate Receptors
  作者：Umberto M. Battisti、Krzysztof Jozwiak、Giuseppe Cannazza、Giulia Puia、Gabriella Stocca、Daniela Braghiroli、Carlo Parenti、Livio Brasili、Marina M. Carrozzo、Cinzia Citti、Luigino Troisi

  DOI：10.1021/ml200184w

  日期：2012.1.12

  The potential therapeutic benefit of compounds able to activate AMPA receptors (AMPAr) has led to the search for new AMPAr positive modulators. On the basis of crystallographic data of the benzothiadiazines binding mode in the S1S2 GluA2 dimer interface, a set of 5-aryl-2,3-dihydrobenzothiadiazine type compounds has been synthesized and tested. Electrophysiological results suggested that 5-heteroaryl substituents on the benzothiadiazine core like 3-furanyl and 3-thiophenyl dramatically enhance the activity as positive modulators of AMPAr with respect to IDRA21 and cyclothiazide. Mouse brain microdialysis studies have suggested that 7-chloro-5-(3-furyl)-3-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide crosses the blood-brain barrier after intraperitoneal injection. Biological results have been rationalized by a computational docking simulation that it has currently employed to design new AMPAr-positive modulator candidates.