3,4-Dihydro-4-methyl-2H-1,2,4-benzothiadiazin-3-on-1,1-dioxid | 13338-02-8

• 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: 3,4-Dihydro-4-methyl-2H-1,2,4-benzothiadiazin-3-on-1,1-dioxid
• 英文别名: 4-methyl-2H-benzo[e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxide；4-methyl-1,1-dioxo-1,4-dihydrobenzo[1,2,4]thiadiazin-3-one；4-methyl-2H-1,2,4-benzothiadiazine-3 (4H)-one 1,1-dioxide；4-methyl-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxide；4-methyl-1,1-dioxo-1,4-dihydro-2H-1λ⁶-benzo[1,2,4]thiadiazin-3-one；4-methyl-1,1-dioxo-4H-1λ⁶-benzo[e][1,2,4]thiadiazin-3-one；4-methyl-3,4-dihydro-2H-1lambda6,2,4-benzothiadiazine-1,1,3-trione；4-methyl-1,1-dioxo-1λ6,2,4-benzothiadiazin-3-one
• CAS: 13338-02-8
• 化学式: C₈H₈N₂O₃S
• 分子量: 212.229
• InChiKey: RQCMUVKZNMGOOY-UHFFFAOYSA-N

物化性质

• 熔点：
  241-242 °C
• 密度：
  1.449±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 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：
  74.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-Dihydro-4-methyl-2H-1,2,4-benzothiadiazin-3-on-1,1-dioxid 在 sodium tetrahydroborate 作用下， 以 甲醇 、 氯仿 、 异丙醇 为溶剂， 反应 27.0h， 生成 2-甲基氨基苯磺酰胺
  参考文献：
  名称：

  Ringerweiterung冯sechs-つneungliedrigen Heterocyclen：Umsetzung冯3-（二甲氨基）-2,2-二甲基-2- ħ -azirin MIT 3,4-二氢-2- ħ -1,2,4-苯并噻二嗪3对1， 1-二氧化物†

  摘要：

  六至九元杂环的环扩大：3-（二甲氨基）-2,2-二甲基-2 H-叠氮基与3,4-二氢-2 H -1,2,4-苯并噻二嗪-3-酮的反应1,1-二氧化物

  DOI：

  10.1002/hlca.19930760626
• 作为产物：
  描述：

  (4-methyl-1,1-dioxo-1,4-dihydro-1λ⁶-benzo[1,2,4]thiadiazin-3-yl)-phenyl-amine 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 3,4-Dihydro-4-methyl-2H-1,2,4-benzothiadiazin-3-on-1,1-dioxid
  参考文献：
  名称：

  Raffa; Melegari; Vampa, Farmaco, Edizione Scientifica, 1972, vol. 27, # 6, p. 509 - 516

  摘要：

  DOI：

文献信息

• Heterocyclization of N-(chlorosulfonyl)imidoyl chlorides with anilines, a new method of synthesis of 1,2,4-benzothiadiazine 1,1-dioxides
  作者：Alexander A. Shalimov、Tetyana I. Chudakova、Yurii G. Vlasenko、Anatoly D. Sinitsa、Petro P. Onys’ko

  DOI：10.1007/s10593-016-1873-z

  日期：2016.4

  N-(Chlorosulfonyl)imidoyl chlorides react regioselectively with anilines, 2-aminomethylnaphthaline, or 1,2,3,4-tetrahydroquinoline leading to derivatives of 1,2,4-benzothiadiazine 1,1-dioxide. Heterocyclization occurs at the sterically less hindered C-6 atom in the case of 3-methoxy- and 3,4-dimethoxyaniline, while the reaction with 3-methylaniline leads to a mixture of cyclization products at the

  N-（氯磺酰基）亚氨基氯与苯胺，2-氨基甲基萘或1,2,3,4-四氢喹啉在区域上选择性反应，生成1,2,4-苯并噻二嗪1,1-二氧化物的衍生物。在3-甲氧基-和3,4-二甲氧基苯胺的情况下，杂环在较少受阻的C-6原子处发生，而与3-甲基苯胺的反应导致在C-2和C-6原子处环化产物的混合物苯胺
• Synthesis, structure analysis, and antibacterial activity of some novel 10-substituted 2-(4-piperidyl/phenyl)-5,5-dioxo[1,2,4]triazolo[1,5-b][1,2,4]benzothiadiazine derivatives
  作者：Ahmed Kamal、M. Naseer A. Khan、K. Srinivasa Reddy、K. Rohini、G. Narahari Sastry、B. Sateesh、B. Sridhar

  DOI：10.1016/j.bmcl.2007.07.043

  日期：2007.10

  10-dihydro[1,2,4]triazolo[1,5-b]-[1,2,4]benzothiadiazine arylsulfonamide derivatives (10a-j and 13a-f) was synthesized. The structures of these compounds were confirmed on the basis of spectral data, elemental analysis, X-ray analysis, and quantum chemical calculations. These compounds were evaluated for their efficacy as antibacterial agents against various Gram-positive and Gram-negative strains of bacteria

  新的10-取代的5,5-二氧-5,10-二氢[1,2,4]三唑[1,5-b]-[1,2,4]苯并噻二嗪芳基磺酰胺衍生物系列（10a-j和13a -f）被合成。这些化合物的结构在光谱数据，元素分析，X射线分析和量子化学计算的基础上得到确认。评价了这些化合物作为针对各种革兰氏阳性和革兰氏阴性细菌的抗菌剂的功效。在这些化合物10f和10i中，对大肠杆菌的活性最高，对大肠杆菌和枯草芽孢杆菌的活性最高的化合物13e。此外，与标准药物相比，其他化合物也显示出有效的抑制活性。
• [EN] NOVEL ANTI-INFECTIVES<br/>[FR] NOUVEAUX ANTI-INFECTIEUX
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2002098424A1

  公开（公告）日：2002-12-12

  Compounds useful as HCV anti-infectives having the formula: wherein the formula variables are as defined herein, are disclosed. Also disclosed are methods of making and using the same.

  本发明揭示了具有以下式的HCV抗感染剂有用的化合物：其中，公式变量如本文所定义。同时还揭示了制备和使用该化合物的方法。
• Novel anti-infectives
  申请人：——

  公开号：US20040147739A1

  公开（公告）日：2004-07-29

  Compounds useful as HCV anti-infectives having the formula: wherein the formula variables are as defined herein, are disclosed. Also disclosed are methods of making and using the same.

  本文披露了具有以下公式的HCV抗感染剂有用的化合物：其中公式变量如本文所定义。同时，还披露了制备和使用这些化合物的方法。
• 3-(1,1-Dioxo-2<i>H</i>-(1,2,4)-benzothiadiazin-3-yl)-4-hydroxy-2(1<i>H</i>)-quinolinones, Potent Inhibitors of Hepatitis C Virus RNA-Dependent RNA Polymerase
  作者：Rosanna Tedesco、Antony N. Shaw、Ramesh Bambal、Deping Chai、Nestor O. Concha、Michael G. Darcy、Dashyant Dhanak、Duke M. Fitch、Adam Gates、Warren G. Gerhardt、Dina L. Halegoua、Chao Han、Glenn A. Hofmann、Victor K. Johnston、Arun C. Kaura、Nannan Liu、Richard M. Keenan、Juili Lin-Goerke、Robert T. Sarisky、Kenneth J. Wiggall、Michael N. Zimmerman、Kevin J. Duffy

  DOI：10.1021/jm050855s

  日期：2006.2.1

  Recently, we disclosed a new class of HCV polymerase inhibitors discovered through high-throughput screening (HTS) of the GlaxoSmithKline proprietary compound collection. This interesting class of 3-(1,1-dioxo-2H-1,2,4-benzothiadiazin-3-yl)-4-hydroxy-2(1H)-quinolinones potently inhibits HCV polymerase enzymatic activity and inhibits the ability of the subgenomic HCV replicon to replicate in Huh-7 cells. This report will focus on the structure-activity relationships (SAR) of substituents on the quinolinone ring, culminating in the discovery of 1-(2-cyclopropylethyl)-3-(1,1-dioxo-2H-1,2,4-benzothiadiazin-3-yl)-6-fluoro-4-hydroxy-2(1H)-quinolinone (130), an inhibitor with excellent potency in biochemical and cellular assays possessing attractive molecular properties for advancement as a clinical candidate. The potential for development and safety assessment profile of compound 130 will also be discussed.