2-cyano-N-hydroxybenzenesulfonamide

• 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-cyano-N-hydroxybenzenesulfonamide
• 化学式: C₇H₆N₂O₃S
• 分子量: 198.202
• InChiKey: RMRNLOFQVMCESZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  98.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-cyano-N-hydroxybenzenesulfonamide 在 氧气 作用下， 以 水 为溶剂， 生成 一氧化二氮
  参考文献：
  名称：

  WO2007/109175

  摘要：

  公开号：
• 作为产物：
  描述：

  2-氰基苯磺酰氯 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32%的产率得到2-cyano-N-hydroxybenzenesulfonamide
  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：The Johns Hopkins University

  公开号：EP3124471A1

  公开（公告）日：2017-02-01

  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.

  本发明涉及N-羟基磺酰胺衍生物，该衍生物可在生理条件下捐献硝酰（HNO），并可用于治疗和/或预防对硝酰治疗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- 羟基磺酰胺衍生物可在生理条件下以可控速率释放 NHO，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。
• NITROXYL DONORS FOR THE TREATMENT OF PULMONARY HYPERTENSION
  申请人：Cardioxyl Pharmaceuticals, Inc.

  公开号：EP2504003B1

  公开（公告）日：2016-11-09
• N-hydroxylsulfonamide derivatives as new physiologically useful nitroxyl donors
  申请人：The Johns Hopkins University

  公开号：EP2586434B1

  公开（公告）日：2016-04-27
• Nitroxyl Progenitors for the Treatment of Pulmonary Hypertension
  申请人：Mazhari Reza

  公开号：US20110160200A1

  公开（公告）日：2011-06-30

  The invention relates to methods of treating, preventing or delaying the onset or development of pulmonary hypertension using hydroxyl donors or pharmaceutically acceptable salts thereof. The invention further relates to methods of reducing mean pulmonary arterial pressure using hydroxyl donors or pharmaceutically acceptable salts thereof.
• 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.