2-nitro-N-hydroxybenzenesulfonamide | 217463-52-0

• 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-nitro-N-hydroxybenzenesulfonamide
• 英文别名: N-Hydroxy-2-nitrobenzenesulfonamide
• CAS: 217463-52-0
• 化学式: C₆H₆N₂O₅S
• mdl: MFCD18072514
• 分子量: 218.19
• InChiKey: CDRGZNIXJYUKQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 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：
  121
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  邻硝基苯磺酰氯 在 盐酸羟胺 、 magnesium oxide 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以97%的产率得到2-nitro-N-hydroxybenzenesulfonamide
  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。
• METHOD FOR PRODUCING 3-SUBSTITUTED-4-FLUOROPYRROLIDINE DERIVATIVE
  申请人：Suzuki Masashi

  公开号：US20130085282A1

  公开（公告）日：2013-04-04

  An inexpensive and industrially advantageous method for producing optically active syn-3-(N-substituted-aminomethyl)-4-fluoropyrrolidine which may be an intermediate for producing pharmaceuticals is provided. The present invention relates a method for producing a syn-1-protected-4-fluoro-3-(N-substituted-N-nitrobenzenesulfonyl)pyrrolidine derivative or it's enantiomer, or their salts comprising the process of fluorinating a compound represented by the general formula (6) (in the formula, PG 1 represents a protecting group for an amino group, R 1 represents a C1 to C6 alkyl group which may be substituted or a C3 to C8 cycloalkyl group which may be substituted, and Ns represents a 2-nitrobenzenesulfonyl group or a 4-nitrobenzenesulfonyl group) or it's enantiomer using a nucleophilic fluorinating agent and an organic base having an amidine or guanidine structure.

  提供了一种廉价且工业上优势的方法，用于生产光学活性的syn-3-(N-取代氨甲基)-4-氟吡咯烷，该化合物可能是生产药物的中间体。本发明涉及一种生产syn-1-保护的-4-氟-3-(N-取代-N-硝基苯磺酰基)吡咯烷衍生物或其对映体或其盐的方法，包括将通式（6）所代表的化合物（其中，PG1代表氨基的保护基，R1代表可取代的C1到C6烷基或可取代的C3到C8环烷基，Ns代表2-硝基苯磺酰基或4-硝基苯磺酰基）或其对映体使用亲核氟化试剂和具有酰胺或鸟嘌呤结构的有机碱进行氟化的过程。
• 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。
• PROCESS FOR PREPARATION OF 3-SUBSTITUTED-4-FLUOROPYRROLIDINE DERIVATIVES
  申请人：Kyorin Pharmaceutical Co., Ltd.

  公开号：EP2578568A1

  公开（公告）日：2013-04-10

  An inexpensive and industrially advantageous method for producing optically active syn-3-(N-substituted-aminomethyl)-4-fluoropyrrolidine which may be an intermediate for producing pharmaceuticals is provided. The present invention relates a method for producing a syn-1-protected-4-fluoro-3-(N-substituted-N-nitrobenzenesulfonyl)pyrrolidine derivative or it's enantiomer, or their salts comprising the process of fluorinating a compound represented by the general formula (6) (in the formula, PG1 represents a protecting group for an amino group, R1 represents a C1 to C6 alkyl group which may be substituted or a C3 to C8 cycloalkyl group which may be substituted, and Ns represents a 2-nitrobenzenesulfonyl group or a 4-nitrobenzenesulfonyl group) or it's enantiomer using a nucleophilic fluorinating agent and an organic base having an amidine or guanidine structure.

  本发明提供了一种生产具有光学活性的合成-3-(N-取代-氨甲基)-4-氟吡咯烷的廉价且具有工业优势的方法，该方法可作为生产药物的中间体。本发明涉及一种生产受 syn-1 保护的-4-氟-3-(N-取代-N-硝基苯磺酰基)吡咯烷衍生物或其对映体或它们的盐的方法，包括将通式 (6) 所代表的化合物氟化的过程（式中，PG1 代表氨基的保护基团、R1 代表可能被取代的 C1 至 C6 烷基或可能被取代的 C3 至 C8 环烷基，Ns 代表 2-硝基苯磺酰基或 4-硝基苯磺酰基）或其对映体，使用亲核氟化剂和具有脒基或胍基结构的有机碱。
• 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。