| 428866-71-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• CAS: 428866-71-1
• 化学式: C₆H₁₂N₃O₂*Na
• 分子量: 181.17
• InChiKey: CQDVBJLHKKUTAB-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.76
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  64.73
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  、 4-溴甲基苯硼酸频哪醇酯 在 15-冠醚-5 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.08h， 以12%的产率得到1-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4-methyl[(2-methylpiperidinyl)diazen-1-ium-1,2-diol-2-ate]
  参考文献：
  名称：

  Arylboronate Ester Based Diazeniumdiolates (BORO/NO), a Class of Hydrogen Peroxide Inducible Nitric Oxide (NO) Donors

  摘要：

  Here, we report the design, synthesis, and evaluation of arylboronate ester based diazeniumdiolates (BORO/NO), a class of nitric oxide (NO) donors activated by hydrogen peroxide (H2O2), a reactive oxygen species (ROS), to generate NO. We provide evidence for the NO donors' ability to permeate bacteria to produce NO when exposed to H2O2 supporting possible applications for BORO/NO to study molecular mechanisms of NO generation in response to elevated ROS.

  DOI：

  10.1021/ol5010643

文献信息

• 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.
• Nitroreductase-activated nitric oxide (NO) prodrugs
  作者：Kavita Sharma、Kundan Sengupta、Harinath Chakrapani

  DOI：10.1016/j.bmcl.2013.08.066

  日期：2013.11

  Due to the involvement of nitric oxide (NO) in numerous and diverse physiological processes, site-directed delivery of therapeutic NO in order to minimize unwanted side-effects is necessary. O-2-(4-Nitrobenzyl) diazeniumdiolates are designed as substrates for Escherichia coli nitroreductase (NTR), an enzyme that is frequently used to facilitate directed delivery of cytotoxic species to cancers. O-2-(4-Nitrobenzyl) diazeniumdiolates are found to be stable in aqueous buffer but are metabolized by NTR to produce NO. A cell viability assay revealed that cytotoxic effects of O-2-(4-nitrobenzyl)1-(2-methylpiperidin-1-yl)diazen-1-ium-1,2-diolate (4b) towards two cancer cell lines is significantly enhanced in the presence of NTR suggesting the potential for use of this compound in nitric oxide-based directed prodrug therapy. (C) 2013 Elsevier Ltd. All rights reserved.