N-hydroxy-2,4,6-triisopropylbenzenesulfonamide

• 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-2,4,6-triisopropylbenzenesulfonamide
• 英文别名: N-hydroxy-2,4,6-triisopropylbenzensulfonamide；2,4,6-tri-isopropyl-N-hydroxybenzenesulfonamide；N-hydroxy-2,4,6-tri(propan-2-yl)benzenesulfonamide
• 化学式: C₁₅H₂₅NO₃S
• 分子量: 299.434
• InChiKey: YWZWWGLSOOIVSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-hydroxy-2,4,6-triisopropylbenzenesulfonamide 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：

  2,4,6-三异丙基苯磺酰氯 在 盐酸羟胺 、 magnesium oxide 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以90%的产率得到N-hydroxy-2,4,6-triisopropylbenzenesulfonamide
  参考文献：
  名称：

  A Straightforward Route to Piloty’s Acid Derivatives: A Class of Potential Nitroxyl-Generating Prodrugs

  摘要：

  一系列Piloty的酸衍生物在温和且中性的条件下容易制备。最终产物易于分离，提供了显著优于知名工艺的优势。这种方法特别有吸引力，因为它能干净利落地提供低分子量的脂肪族磺酰羟肟酸，这些化合物因其生理条件下产生HNO的倾向而具有很大的研究价值。

  DOI：

  10.1055/s-0029-1217565

文献信息

• A Straightforward Route to Piloty’s Acid Derivatives: A Class of Potential Nitroxyl-Generating Prodrugs
  作者：Andrea Porcheddu、Lidia De Luca、Giampaolo Giacomelli

  DOI：10.1055/s-0029-1217565

  日期：2009.8

  A series of Piloty’s acid derivatives were easily prepared under mild and neutral conditions. The ease of isolation of the final product offers a marked advantage over well-known procedures. This methodology is particularly attractive as it cleanly provided low molecular weight aliphatic sulfohydroxamic acids, which are very interesting for their tendency to generate HNO under physiological conditions.

  一系列Piloty的酸衍生物在温和且中性的条件下容易制备。最终产物易于分离，提供了显著优于知名工艺的优势。这种方法特别有吸引力，因为它能干净利落地提供低分子量的脂肪族磺酰羟肟酸，这些化合物因其生理条件下产生HNO的倾向而具有很大的研究价值。
• N-hydroxylsulfonamide derivatives as new physiologically useful nitroxyl donors
  申请人：Johns Hopkins University School of Medicine

  公开号：EP2489350A1

  公开（公告）日：2012-08-22

  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。
• 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。
• Piloty’s acid derivative with improved nitroxyl-releasing characteristics
  作者：Kazuyuki Aizawa、Hidehiko Nakagawa、Kazuya Matsuo、Kodai Kawai、Naoya Ieda、Takayoshi Suzuki、Naoki Miyata

  DOI：10.1016/j.bmcl.2013.02.062

  日期：2013.4

  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.
• 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