(S)-1-[2-(hydroxymethyl)pyrrolidin-1-yl]diazen-1-ium-1,2-diolate sodium salt | 949888-30-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (S)-1-[2-(hydroxymethyl)pyrrolidin-1-yl]diazen-1-ium-1,2-diolate sodium salt
• 英文别名: sodium 1-[2S-(hydroxymethyl)pyrrolidin-1-yl]diazen-1-ium-1,2-diolate
• CAS: 949888-30-6；1177456-95-9
• 化学式: C₅H₁₀N₃O₃*Na
• 分子量: 183.142
• InChiKey: OWPZVDBARLVLSM-JEDNCBNOSA-M

物化性质

• 熔点：
  142-144 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -3.18
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  84.96
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-1-[2-(hydroxymethyl)pyrrolidin-1-yl]diazen-1-ium-1,2-diolate sodium salt 在 4-二甲氨基吡啶 、 15-冠醚-5 、 碳酸氢钠 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.08h， 生成 (S)-O2-(2-acetylthioethyl) 1-[2-(acetoxymethyl)pyrrolidin-1-yl]diazen-1-ium-1,2-diolate
  参考文献：
  名称：

  O²-(N-Hydroxy(methoxy)-2-ethanesulfonamido) Protected Diazen-1-ium-1,2-diolates: Nitric Oxide Release via a Base-Induced β-Elimination Cleavage

  摘要：

  O-2-(Ethanesulfohydroxamic acid) and O-2-(N-methoxy-2-ethanesulfonylamido) diazen-1-ium-1,2-diolates (4-7), a novel type of O-2-(protected) diazeniumdiolate, were synthesized using a key thioacetate oxidation reaction. Nitric oxide release studies showed that O-2-(N-methoxy-2-ethanesulfonylamido) diazeniumdiolates 5 and 7 released NO in a nonphysiological alkaline buffer, in the presence of bases such as the basic natural amino acids Arg and His, or the non-nucleophilic organic base DBU in PBS at pH 7.4, via a beta-elimination cleavage reaction.

  DOI：

  10.1021/ol200053z
• 作为产物：
  描述：

  L-脯氨醇 在 甲醇 、 titanium(IV) oxide 、 sodium methylate 、 硝基二甲基苯基 作用下， 以 乙醚 为溶剂， 反应 48.0h， 生成 (S)-1-[2-(hydroxymethyl)pyrrolidin-1-yl]diazen-1-ium-1,2-diolate sodium salt
  参考文献：
  名称：

  Identification of nitric oxide-releasing derivatives of oleanolic acid as potential anti-colon cancer agents

  摘要：

  NO释放杂交物6调节结肠癌相关信号通路，在体外和体内展现出强大的抗结肠癌活性。

  DOI：

  10.1039/c5ra00270b

文献信息

• DIAZENIUMDIOLATED NON-STEROIDAL ANTI-INFLAMMATORY DRUGS, COMPOSITIONS THEREOF, AND RELATED METHODS
  申请人：Velázquez Carlos A.

  公开号：US20090186859A1

  公开（公告）日：2009-07-23

  Disclosed are compounds that release nitric oxide, e.g., a compound of Formula (I) wherein R 1-10 , X, and n are as described herein, which are NSAID derivatives comprising a diazeniumdiolate moiety N 2 O 2 − . The compounds are chemopreventive agents with gastric-sparing, analgesic, cardioprotective, and/or anti-inflammatory properties. Also disclosed is a pharmaceutical composition comprising a compound of the invention and a pharmaceutically acceptable carrier. Also disclosed is a method of preventing or treating cancer or treating inflammation or an inflammation-related condition in a mammal comprising administering an effective amount of a compound of the invention to the mammal.

  披露了释放一氧化氮的化合物，例如，式(I)的化合物，其中R1-10、X和n如本文所述，这些化合物是非甾体抗炎药（NSAID）衍生物，包含亚硝基二醇基团N2O2−。这些化合物是具有胃保护、镇痛、心脏保护和/或抗炎特性的化学预防剂。还披露了一种药物组合物，包括本发明的化合物和药用载体。还披露了一种预防或治疗癌症或治疗炎症或炎症相关状况的方法，包括向哺乳动物施用本发明的化合物的有效量。
• Aryl Bis(diazeniumdiolates): Potent Inducers of <i>S</i>-Glutathionylation of Cellular Proteins and Their in Vitro Antiproliferative Activities
  作者：Daniela Andrei、Anna E. Maciag、Harinath Chakrapani、Michael L. Citro、Larry K. Keefer、Joseph E. Saavedra

  DOI：10.1021/jm800831y

  日期：2008.12.25

  A number of bis(diazeniumdiolates) that we designed to release up to 4 mol of nitric oxide (NO) and that are structural analogues of the NO prodrug and anticancer lead compound O-2-2,4-dinitro-5-[4-(N-methylamino)benzoyloxy]phenyl} 1-(N,N-dimethylamino)diazen-1-ium-1,2-diolate (PABA/NO) were synthesized and studied. A majority of these compounds yielded higher levels of NO, were better inhibitors of proliferation of a number of cancer cell lines, and more rapidly induced substantially increased levels of S-glutathionylation of cellular proteins in comparison with PABA/NO. In most cases, the antiproliferative activity and extents of S-glutathionylation correlated well with levels of intracellular NO release. We report bis(diazeniumdiolates) to be a class of S-glutathionylating agents with potent antiproliferative and S-glutathionylating activity.
• [EN] ANGIOTENSIN II RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DES RÉCEPTEURS DE L'ANGIOTENSINE II
  申请人：MERCK & CO INC

  公开号：WO2009099853A8

  公开（公告）日：2009-10-08
• <i>O</i>²-(<i>N</i>-Hydroxy(methoxy)-2-ethanesulfonamido) Protected Diazen-1-ium-1,2-diolates: Nitric Oxide Release via a Base-Induced β-Elimination Cleavage
  作者：Zhangjian Huang、Edward E. Knaus

  DOI：10.1021/ol200053z

  日期：2011.3.4

  O-2-(Ethanesulfohydroxamic acid) and O-2-(N-methoxy-2-ethanesulfonylamido) diazen-1-ium-1,2-diolates (4-7), a novel type of O-2-(protected) diazeniumdiolate, were synthesized using a key thioacetate oxidation reaction. Nitric oxide release studies showed that O-2-(N-methoxy-2-ethanesulfonylamido) diazeniumdiolates 5 and 7 released NO in a nonphysiological alkaline buffer, in the presence of bases such as the basic natural amino acids Arg and His, or the non-nucleophilic organic base DBU in PBS at pH 7.4, via a beta-elimination cleavage reaction.
• Identification of nitric oxide-releasing derivatives of oleanolic acid as potential anti-colon cancer agents
  作者：Junjie Fu、Yu Zou、Zhangjian Huang、Chang Yan、Qimeng Zhou、Huibin Zhang、Yisheng Lai、Sixun Peng、Yihua Zhang

  DOI：10.1039/c5ra00270b

  日期：——

  NO-releasing hybrid6regulates colon cancer-related signaling pathways, exhibiting potent anti-colon cancer activityin vitroandin vivo.

  NO释放杂交物6调节结肠癌相关信号通路，在体外和体内展现出强大的抗结肠癌活性。