4-Methyl-1,2,4-benzothiadiazin-1,1-dioxid | 7752-12-7

• 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-1,2,4-benzothiadiazin-1,1-dioxid
• 英文别名: 4-Methyl-1,2,4-benzthiadiazin-1,1-dioxid；4-methyl-4H-benzo[e][1,2,4]thiadiazine 1,1-dioxide；4-methyl-1,2,4-benzothiadiazine-1,1-dioxide；4-methyl-4H-1,2,4-benzothiadiazine 1,1-dioxide；4-methyl-1λ6,2,4-benzothiadiazine 1,1-dioxide
• CAS: 7752-12-7
• 化学式: C₈H₈N₂O₂S
• 分子量: 196.23
• InChiKey: GAMOILWTJHUYFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 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：
  58.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Methyl-1,2,4-benzothiadiazin-1,1-dioxid 在 sodium tetrahydroborate 作用下， 以 异丙醇 为溶剂， 反应 0.75h， 以72%的产率得到4-Methyl-3,4-dihydro-1,2,4-benzothiadiazin-1,1-dioxid
  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：

  NSC 373853 、 N-3-[3-(1-哌啶甲基)-苯氧基]丙胺 在 3-[N-]3-[3-(piperidinomethyl)phenoxy]-propyl 、 amino 作用下， 以to obtain 3-[N-]3-[3-(piperidinomethyl)phenoxy]-propyl]amino)-4-methyl-1,2,4-benzothiadiazine-1,1-dioxide的产率得到4-Methyl-1,2,4-benzothiadiazin-1,1-dioxid
  参考文献：
  名称：

  Benzothiadiazine derivatives

  摘要：

  苯并噻二嗪衍生物，其水合物和酸加成盐，该衍生物由通式（I）表示，其中X是亚甲基或取代有低碳基的氮原子，Y和Z分别是亚甲基或羰基，A是苯基或取代有甲氧羰基的苯基，R.sub.4是低碳基或低烯基，R.sub.1是氢原子，乙酰氧乙酰基，环己基甲基或苄基，其中苯环可能被取代有低碳氧基，卤原子，硝基，低碳基，亚甲二氧基或羟基，R.sub.2是低碳基或苯基，R.sub.3是氢原子，卤原子或低碳氧基，但当X、Y和Z分别为亚甲基，A为未取代的苯基，R.sub.4为低碳基且R.sub.1为氢原子时除外；以及作为有效成分含有上述衍生物、水合物或酸加成盐的消化性溃疡治疗剂。

  公开号：

  US05401739A1

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.
• Benzothiadiazine derivatives
  申请人：Taiho Pharmaceutical Co. Ltd.

  公开号：US05401739A1

  公开（公告）日：1995-03-28

  A benzothiadiazine derivative, hydrate thereof and acid addition salt thereof, the derivative being represented by the general formula (I) ##STR1## wherein X is methylene or a nitrogen atom substituted with a lower alkyl, Y and Z are each methylene or carbonyl, A is phenylene or phenylene substituted with methoxycarbonyl, R.sub.4 is lower alkylene or lower alkenylene, R.sub.1 is a hydrogen atom, acetoxyacetyl, cyclohexylmethyl or benzyl wherein the benzene ring may be substituted with lower alkoxyl, halogen atom, nitro, lower alkyl, methylenedioxy or hydroxyl, R.sub.2 is lower alkyl or phenyl, and R.sub.3 is a hydrogen atom, halogen atom or lower alkoxyl with the exception of the case where X, Y and Z are each methylene, A is unsubstituted phenylene, R.sub.4 is lower alkylene and R.sub.1 is a hydrogen atom; and a peptic ulcer treating agent containing as an effective component the above derivative, hydrate thereof or acid addition salt thereof.

  苯并噻二嗪衍生物，其水合物和酸加成盐，该衍生物由通式（I）表示，其中X是亚甲基或取代有低碳基的氮原子，Y和Z分别是亚甲基或羰基，A是苯基或取代有甲氧羰基的苯基，R.sub.4是低碳基或低烯基，R.sub.1是氢原子，乙酰氧乙酰基，环己基甲基或苄基，其中苯环可能被取代有低碳氧基，卤原子，硝基，低碳基，亚甲二氧基或羟基，R.sub.2是低碳基或苯基，R.sub.3是氢原子，卤原子或低碳氧基，但当X、Y和Z分别为亚甲基，A为未取代的苯基，R.sub.4为低碳基且R.sub.1为氢原子时除外；以及作为有效成分含有上述衍生物、水合物或酸加成盐的消化性溃疡治疗剂。