2-fluoro-5-(trifluoromethyl)benzenesulfonamide | 217454-98-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-fluoro-5-(trifluoromethyl)benzenesulfonamide
• 英文别名: 2-fluoro-5-trifluoromethylbenzenesulphonamide；2-Fluoro-5-(trifluoromethyl)benzene sulfonamide
• CAS: 217454-98-3
• 化学式: C₇H₅F₄NO₂S
• mdl: MFCD12026239
• 分子量: 243.182
• InChiKey: UQNWALSRFRMXJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-fluoro-5-(trifluoromethyl)benzenesulfonamide 在 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 、 异丙醇 为溶剂， 反应 24.0h， 生成 4-cyclopropyl-7-trifluoromethyl-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide
  参考文献：
  名称：

  Synthesis, Pharmacological and Structural Characterization, and Thermodynamic Aspects of GluA2-Positive Allosteric Modulators with a 3,4-Dihydro-2H-1,2,4-benzothiadiazine 1,1-Dioxide Scaffold

  摘要：

  Positive allosteric modulators of ionotropic glutamate receptors are potential compounds for treatment of cognitive disorders, e.g., Alzheimer's disease. The modulators bind within the dimer interface of the ligand-binding domain (LBD) and stabilize the agonist-bound conformation, thereby slowing receptor desensitization and/or deactivation. Here we describe the synthesis and pharmacological testing at GluA2 of a new generation of 3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxides. The most potent modulator 3 in complex with GluA2-LBD-L483Y-N754S was subjected to structural analysis by X-ray crystallography, and the thermodynamics of binding was studied by isothermal titration calorimetry. Compound 3 binds to GluA2-LBD-L483Y-N754S with a K-d of 0.35 mu M (Delta H = -7.5 kcal/mol and -T Delta S = -1.3 kcal/mol). This is the first time that submicromolar binding affinity has been achieved for this type of positive allosteric modulator. The major structural factor increasing the binding affinity of 3 seems to be interactions between the cyclopropyl group of 3 and the backbone of Phe495 and Met496.

  DOI：

  10.1021/jm4012092
• 作为产物：
  描述：

  2-氟-5-(三氟甲基)苯磺酰氯 在 氨 作用下， 以 二氯甲烷 为溶剂， 以97%的产率得到2-fluoro-5-(trifluoromethyl)benzenesulfonamide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 4-Chloro-3,5-dinitrobenzotrifluoride Analogues as Antileishmanial Agents

  摘要：

  Desnitro analogues of 4-chloro-3,5-dinitrobenzotrifluoride (chloralin) (2), an in vitro microtubule inhibitor of several Leishmania species, have been synthesized from 2-halo-5-(trifluoromethyl)benzenesulfonyl chlorides 4 and 5. The analogues exhibited moderate to excellent activity when tested against Leishmania donovani amastigotes in vitro. Two representative compounds, 7f and 8, were tested against the Khartoum strain of L. donovani in a hamster model using chloralin (2) and Glucantime (one of the current therapeutics of choice in the treatment of Leishmania) as standards, the results of which will be discussed herein.

  DOI：

  10.1021/jm9804073

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。
• Polymers containing grafted bis(sulfonyl)imide sodium or lithium salts, methods for production thereof and uses of same as electrolytes for batteries
  申请人：CDP INNOVATION

  公开号：US10141603B2

  公开（公告）日：2018-11-27

  The invention relates to novel polymers containing grafted sodium or lithium bis(sulfonyl)imides, to the methods for the production thereof, and to the uses of same as electrolytes in batteries.

  本发明涉及含有接枝钠或锂双(磺酰基)亚胺的新型聚合物、其生产方法以及用作电池电解质的用途。
• Discovery of XEN445: A potent and selective endothelial lipase inhibitor raises plasma HDL-cholesterol concentration in mice
  作者：Shaoyi Sun、Richard Dean、Qi Jia、Alla Zenova、Jing Zhong、Celene Grayson、Clark Xie、Andrea Lindgren、Pritpaul Samra、Luis Sojo、Margaret van Heek、Linus Lin、David Percival、Jian-min Fu、Michael D. Winther、Zaihui Zhang

  DOI：10.1016/j.bmc.2013.10.023

  日期：2013.12

  Endothelial lipase (EL) activity has been implicated in HDL metabolism and in atherosclerotic plaque development; inhibitors are proposed to be efficacious in the treatment of dyslipidemia related cardiovascular disease. We describe here the discovery of a novel class of anthranilic acids EL inhibitors. XEN445 (compound 13) was identified as a potent and selective EL inhibitor, that showed good ADME and PK properties, and demonstrated in vivo efficacy in raising plasma HDLc concentrations in mice. (C) 2013 Elsevier Ltd. All rights reserved.
• Nouveaux dérivés de benzothiadiazines cycloalkylées, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent
  申请人：Les Laboratoires Servier

  公开号：EP2147915B1

  公开（公告）日：2010-09-15
• NOUVEAUX POLYMERES CONTENANT DES SELS DE LITHIUM OU DE SODIUM DE BIS(SULFONYL)IMIDES GREFFES, LEURS PROCEDES DE PREPARATION ET LEURS UTILISATIONS COMME ELECTROLYTES POUR BATTERIES
  申请人：CDP-Innovation

  公开号：EP3172264A1

  公开（公告）日：2017-05-31