N-hydroxy-3-trifluoromethylbenzenesulfonamide

• 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: N-hydroxy-3-trifluoromethylbenzenesulfonamide
• 英文别名: N-hydroxy-3-(trifluoromethyl)benzenesulfonamide
• 化学式: C₇H₆F₃NO₃S
• 分子量: 241.191
• InChiKey: ZQFMPAUDTOJXIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-羟基苯硫酚 、 N-hydroxy-3-trifluoromethylbenzenesulfonamide 在 碘 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以75%的产率得到S-4-hydroxyphenyl 3-(trifluoromethyl)benzenesulfonothioate
  参考文献：
  名称：

  An iodine-mediated new avenue to sulfonylation employing N-hydroxy aryl sulfonamide as a sulfonylating agent

  摘要：

  一种新颖且高效的I₂/K₂CO₃介导的对硫醚酚、芳基乙炔酸和芳基炔烃的选择性磺酰化方法，使用N-羟基磺胺酸盐。

  DOI：

  10.1039/d1ob00036e
• 作为产物：
  描述：

  3-三氟甲基苯磺酰氯 在 4-二甲氨基吡啶 、 盐酸羟胺 作用下， 以 吡啶 为溶剂， 反应 0.08h， 以85%的产率得到N-hydroxy-3-trifluoromethylbenzenesulfonamide
  参考文献：
  名称：

  Piloty’s acid derivative with improved nitroxyl-releasing characteristics

  摘要：

  Recent studies have shown that nitroxyl (HNO) ((HNO)-H-1/(NO)-N-3 ), which is the one-electron-reduced form of nitric oxide (NO), has unique biological activities, especially in the cardiovascular system, and HNO-releasing agents may have therapeutic potential. Since few HNO donors are available for use under physiological conditions, we synthesized and evaluated a series of Piloty's acid (PA) derivatives and evaluated their HNO-releasing activity under physiological conditions. N-Hydroxy-2-nitrobenzenesulfonamide (17) was the most efficient HNO donor among our synthesized PA derivatives, including the lead compound, 2-bromo-N-hydroxybenzenesulfonamide (2). The high HNO-releasing activity is suggested to be due to electronic and steric effects. Compound 17 may be a useful tool for biological experiments. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.062

文献信息

• N-hydroxylsulfonamide derivatives as new physiologically useful nitroxyl donors
  申请人：Cardioxyl Pharmaceuticals, Inc.

  公开号：US10179765B2

  公开（公告）日：2019-01-15

  The invention relates to N-hydroxysulfonamide derivatives that donate nitroxyl (HNO) under physiological conditions and are useful in treating and/or preventing the onset and/or development of diseases or conditions that are responsive to nitroxyl therapy, including heart failure and ischemia/reperfusion injury. Novel N-hydroxysulfonamide derivatives release HNO at a controlled rate under physiological conditions, and the rate of HNO release is modulated by varying the nature and location of functional groups on the N-hydroxysulfonamide derivatives.

  本发明涉及N-羟基磺酰胺衍生物，该衍生物在生理条件下捐献硝基（HNO），可用于治疗和/或预防对硝基疗法有反应的疾病或病症的发生和/或发展，包括心力衰竭和缺血/再灌注损伤。新型 N- 羟基磺酰胺衍生物在生理条件下以可控速率释放 HNO，HNO 释放速率可通过改变 N- 羟基磺酰胺衍生物上官能团的性质和位置来调节。
• N-HYDROXYLSULFONAMIDE DERIVATIVES AS NEW PHYSIOLOGICALLY USEFUL NITROXYL DONORS
  申请人：The Johns Hopkins University

  公开号：EP3124471B1

  公开（公告）日：2020-06-03
• COMPOSITION AND METHODS FOR THE DESIGN AND DEVELOPMENT OF METALLO-ENZYME INHIBITORS
  申请人：Pellecchia Maurizio

  公开号：US20100041653A1

  公开（公告）日：2010-02-18

  The present disclosure provides compounds having the general structure A or pharmaceutically acceptable salts thereof: R—X  (A) wherein R is an alkyl or aryl moiety comprising heterocyclic structures; and X is a metal-chelatin group selected from: This disclosure further provides a focused library of compounds for use in the discovery and design of metallo-enzyme inhibitors. This fragment-based approach provides an assembly of a library of low molecular weight compounds (MW<300 Da) containing a variety of potential metal-chelating groups. The identification of the inhibitory scaffolds among these compounds provides the initial hit fragments that may be optimized for affinity against a particular target using common medicinal chemistry, structure-based or NMR-based approaches.
• N-Hydroxylsulfonamide Derivatives as New Physiologically Useful Nitroxyl Donors
  申请人：Toscano John P.

  公开号：US20110306614A1

  公开（公告）日：2011-12-15

  The invention relates to N-hydroxysulfonamide derivatives that donate nitroxyl (HNO) under physiological conditions and are useful in treating and/or preventing the onset and/or development of diseases or conditions that are responsive to nitroxyl therapy, including heart failure and ischemia/reperfusion injury. Novel N-hydroxysulfonamide derivatives release NHO at a controlled rate under physiological conditions, and the rate of HNO release is modulated by varying the nature and location of functional groups on the N-hydroxysulfonamide derivatives.
• US8030356B2
  申请人：——

  公开号：US8030356B2

  公开（公告）日：2011-10-04