7-fluoro-4H-1,2,4-benzothiadiazine 1,1-dioxide | 37162-45-1

• 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: 7-fluoro-4H-1,2,4-benzothiadiazine 1,1-dioxide
• 英文别名: 7-fluoro-4H-benzo[e][1,2,4]thiadiazine-1,1-dioxide；7-fluoro-4H-1λ6,2,4-benzothiadiazine 1,1-dioxide
• CAS: 37162-45-1
• 化学式: C₇H₅FN₂O₂S
• 分子量: 200.193
• InChiKey: GGUYGZYFOLFKHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-fluoro-4H-1,2,4-benzothiadiazine 1,1-dioxide 在 sodium hydroxide 、 sodium tetrahydroborate 、 盐酸 作用下， 以 水 为溶剂， 反应 1.0h， 生成 7-Fluoro-2,3-dihydro-4H-1,2,4-benzothiadiazine 1,1-dioxide
  参考文献：
  名称：

  Benzothiadiazine derivatives, preparation method and pharmaceutical compositions containing same

  摘要：

  从式(I)中选择的化合物： 其中，X代表氟、溴、碘或甲基，每个R1和R2，可以相同也可以不同，代表氢或烷基，其异构体（存在时）和与药学上可接受的酸的加成盐。 含有上述化合物的药物制剂可用作AMPA调节剂。

  公开号：

  US06894043B1
• 作为产物：
  描述：

  5-fluoro-2-nitrobenzenesulfonamide 在 tin(II) chloride dihdyrate 作用下， 以 乙醇 为溶剂， 反应 3.7h， 生成 7-fluoro-4H-1,2,4-benzothiadiazine 1,1-dioxide
  参考文献：
  名称：

  一类苯并噻二嗪甲氧基丙烯酸酯类衍生物及其制备方法和用途

  摘要：

  本发明提出一类苯并噻二嗪甲氧基丙烯酸酯类衍生物及其制备方法和用途，该物质具有如下化学结构通式Ⅶ：其中，R1为氢、氟、氯、溴、碘、甲基、乙基、甲氧基或硝基；R2为氢、甲基或苄基。本发明将活性基团3,4‑二氢‑2H‑1,2,4‑苯并噻二嗪1,1‑二氧基替换甲氧基丙烯酸酯类杀菌剂的侧链部分后与其药效团合理拼接，合成了一类结构新颖、广谱、高效、低毒的杀菌剂，其可以与现有的杀菌剂交替使用，避免或延缓抗性产生，制备条件常规、后续处理简便，易于实现工业化。

  公开号：

  CN111410638B

文献信息

• Cycloalkylated benzothiadiazines, a process for their preparation and pharmaceutical compostions containing them
  申请人：FRANCOTTE Pierre

  公开号：US20100009974A1

  公开（公告）日：2010-01-14

  Compounds of formula (I): wherein: R Cy represents an unsubstituted or substituted cycloalkyl group or cycloalkylalkyl group, R 1 , R 2 , R 3 and R 4 , which may be the same or different, each represent a hydrogen or halogen atom or a nitro group; a cyano group; a hydroxy group; an alkoxy group; an alkyl group; an unsubstituted or substituted amino group; a carboxy group; an alkoxycarbonyl group; an aryloxycarbonyl group; an unsubstituted or substituted aminocarbonyl group. Medicinal products containing the same which are useful in treating or preventing conditions treatable by an AMPA receptor modulator.

  式（I）的化合物：其中：RCy表示未取代或取代的环烷基或环烷基烷基，R1、R2、R3和R4，可以相同也可以不同，每个代表氢或卤素原子或硝基团；氰基；羟基；烷氧基；烷基；未取代或取代的氨基团；羧基；烷氧羰基；芳基氧羰基；未取代或取代的氨基羰基。含有这些化合物的药物产品，可用于治疗或预防通过AMPA受体调节剂可治疗的疾病。
• Benzene-sulphonamide derivatives and their uses
  申请人：Universite de Liege

  公开号：US06818765B1

  公开（公告）日：2004-11-16

  Benzene-sulphonamide derivatives complying with the general formula (I): in which the different symbols have different meanings, their optical isomers and the salts pharmacologically acceptable of these derivatives, as well as their uses for drug manufacture and as radiolabelled pharmacological tools of the thromboxan A2 receptors.

  苯磺酰胺衍生物符合通式(I)：其中不同符号具有不同的含义，它们的光学异构体和这些衍生物的药理学可接受的盐，以及它们在药物制造和作为血栓素A2受体的放射标记药理学工具中的用途。
• 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.
• Acetic Acid Derivatives of 3,4-Dihydro-2<i>H</i>-1,2,4-benzothiadiazine 1,1-Dioxide as a Novel Class of Potent Aldose Reductase Inhibitors
  作者：Xin Chen、Changjin Zhu、Fan Guo、Xiaowei Qiu、Yanchun Yang、Shuzhen Zhang、Minlan He、Shagufta Parveen、Chaojun Jing、Yan Li、Bing Ma

  DOI：10.1021/jm100962a

  日期：2010.12.9

  A series of novel benzothiadiazine 1,1-dioxide derivatives were synthesized and tested for their inhibitory activity against aldose reductase. Of these derivatives, 17 compounds, having a substituted N2-benzyl group and a N4-acetic acid group on the benzothiadiazine, were found to be potent and selective aldose reductase inhibitors in vitro with IC50 values ranging from 0.032 to 0.975 mu M. 9m proved to be the most active in vitro. The eight top-scoring compounds coming from the in vitro test for ALR2 inhibition activity were then tested in vivo, whereby three derivatives, 9i, 9j, and 9m, demonstrated a significantly preventive effect on sorbitol accumulation in the sciatic nerve in the 5-day streptozotocin-induced diabetic rats in vivo. Structure activity relationship and molecular docking studies highlighted the importance of substitution features of N4-acetic acid group and halogen-substituted N2-benzyl group in the benzothiadiazine scaffold and indicated that substitution with hallogen at C-7 had a remarkably strong effect on ALR2 inhibition potency.
• 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.