7-bromo-4H-1λ6,2,4-benzothiadiazine 1,1-dioxide | 37162-46-2

• 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-bromo-4H-1λ6,2,4-benzothiadiazine 1,1-dioxide
• 英文别名: 7-bromo-4H-1,2,4-benzothiadiazine 1,1-dioxide
• CAS: 37162-46-2
• 化学式: C₇H₅BrN₂O₂S
• 分子量: 261.099
• InChiKey: FLBUFMOQSZMLSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 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：
  3

反应信息

• 作为反应物：
  描述：

  7-bromo-4H-1λ6,2,4-benzothiadiazine 1,1-dioxide 在 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 异丙醇 、 乙腈 为溶剂， 反应 3.75h， 生成 7-Bromo-4-ethyl-2,3-dihydro-4H-1,2,4-benzothiadiazine 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-硝基苯磺酰胺 在 palladium 10% on activated carbon 、 氢气 、 溴 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 60.0 ℃ 、344.75 kPa 条件下， 反应 1.5h， 生成 7-bromo-4H-1λ6,2,4-benzothiadiazine 1,1-dioxide
  参考文献：
  名称：

  1,1-二氧代-4H-苯并[1,2,4]-噻二嗪盐酸盐 类化合物及其制备方法

  摘要：

  本发明公开了一种1,1‑二氧代‑4H‑苯并[1,2,4]‑噻二嗪盐酸盐类化合物及其制备方法，属于有机合成技术领域，本发明的技术方案要点为：1,1‑二氧代‑4H‑苯并[1,2,4]‑噻二嗪盐酸盐类化合物，具有如下结构：，其中R为H、‑CH3或‑C2H5。本发明还公开了该1,1‑二氧代‑4H‑苯并[1,2,4]‑噻二嗪盐酸盐类化合物的制备方法。本发明操作简便易行，原料廉价易得，反应效率较高且重复性较好。

  公开号：

  CN104761514B

文献信息

• Benzothiadiazine derivatives, preparation method and pharmaceutical compositions containing same
  申请人：Pirotte Bernard

  公开号：US06894043B1

  公开（公告）日：2005-05-17

  Compound selected from those of formula (I): wherein: X represents flourine, bromine, iodine or methyl, each of R 1 and R 2 , which may be identical or different, represents hydrogen or alkyl, its isomers when they exist, and addition salts thereof with a pharmaceutically acceptable acid Medicinal products containing the same which are useful as AMPA modulators.

  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。
• Cu-Catalyzed Carbocyclization for General Synthesis of <i>N</i>-Containing Heterocyclics Enabled by BrCF₂COOEt as a C1 Source
  作者：Xiao-Fang Song、Li-Jing Zhang、Xing-Guo Zhang、Hai-Yong Tu

  DOI：10.1021/acs.joc.3c02827

  日期：2024.3.1

  bromodifluoroacetate has been developed. Ethyl bromodifluoroacetate is employed as the C1 source via quadruple cleavage in this transformation. This reaction can afford a variety of N-containing heterocyclics with satisfactory yields and excellent functional group compatibility.

  已经开发出一种实用且高效的铜催化 2-官能化苯胺与溴二氟乙酸乙酯的碳环化反应。在此转化中，溴二氟乙酸乙酯通过四次裂解用作 C1 源。该反应可以得到多种含氮杂环化合物，且产率令人满意，官能团相容性优异。
• RAFFA; MONZANI, Farmaco, Edizione Scientifica, 1963, vol. 18, p. 864 - 870
  作者：RAFFA、MONZANI

  DOI：——

  日期：——
• 356. Derivatives of benz-1 : 2 : 4-thiadiazine 1 : 1-dioxide
  作者：D. V. Parke、R. T. Williams

  DOI：10.1039/jr9500001760

  日期：——
• 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.