4-azidophenylpropanoic acid N-hydroxysuccinimide ester | 149623-45-0

• 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: 4-azidophenylpropanoic acid N-hydroxysuccinimide ester
• 英文别名: 2,5-Dioxopyrrolidin-1-yl 3-(4-azidophenyl)propanoate；(2,5-dioxopyrrolidin-1-yl) 3-(4-azidophenyl)propanoate
• CAS: 149623-45-0
• 化学式: C₁₃H₁₂N₄O₄
• 分子量: 288.263
• InChiKey: GQKNVCXLAWHJAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-azidophenylpropanoic acid N-hydroxysuccinimide ester 在 盐酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 N-(3-methoxy-4-hydroxybenzyl)-3-(4-azidophenyl)propanamide
  参考文献：
  名称：

  Analogs of capsaicin with agonist activity as novel analgesic agents; structure-activity studies. 3. The hydrophobic side-chain "C-region"

  摘要：

  Structural variants of the hydrophobic side chain (''C region'') of the capsaicin molecule have been incorporated into a series of vanillylamides and vanillylthioureas. These compounds have been tested in an in vitro assay for agonism (Ca-45(2+) influx into dorsal root ganglia neurones), previously shown to be predictive of analgesic activity. The results of this study have established the requirement for a hydrophobic substituent of limited size (molar refractivity, MR, <55) in order to obtain high potency. Combination of the information gained here about the ''C-region'' of the capsaicin molecule with the studies described in the preceding two papers provides a rational basis for the design of compounds of increased potency.

  DOI：

  10.1021/jm00068a016
• 作为产物：
  描述：

  3-(4-氨基苯基)丙酸 在 sodium azide 、 硫酸 、 N,N'-二环己基碳二亚胺 、 sodium nitrite 作用下， 以 二氯甲烷 为溶剂， 生成 4-azidophenylpropanoic acid N-hydroxysuccinimide ester
  参考文献：
  名称：

  Analogs of capsaicin with agonist activity as novel analgesic agents; structure-activity studies. 3. The hydrophobic side-chain "C-region"

  摘要：

  Structural variants of the hydrophobic side chain (''C region'') of the capsaicin molecule have been incorporated into a series of vanillylamides and vanillylthioureas. These compounds have been tested in an in vitro assay for agonism (Ca-45(2+) influx into dorsal root ganglia neurones), previously shown to be predictive of analgesic activity. The results of this study have established the requirement for a hydrophobic substituent of limited size (molar refractivity, MR, <55) in order to obtain high potency. Combination of the information gained here about the ''C-region'' of the capsaicin molecule with the studies described in the preceding two papers provides a rational basis for the design of compounds of increased potency.

  DOI：

  10.1021/jm00068a016

文献信息

• Direct Electrochemical Bioconjugation on Metal Surfaces
  作者：Ariel L. Furst、Matthew J. Smith、Matthew B. Francis

  DOI：10.1021/jacs.7b06385

  日期：2017.9.13

  surface coverage could be specified. The advantages of this method were demonstrated through the electrochemical detection of the endocrine disruptor bisphenol A, as well as the capture of living nonadherent cells on electrode surfaces by DNA hybridization. This method not only improves the attachment of DNA to metal surfaces but also represents a new direction for the site-specific attachment of biomolecules

  DNA 具有独特的分子识别和自组装能力，这促进了其广泛整合到对科学和医学有用的设备中。许多这些平台依赖硫醇基团将 DNA 连接到金表面，但这种方法受到缺乏对单层密度的控制以及核苷酸碱基与金属之间的二次相互作用的阻碍。在这项工作中，我们报告了一种电化学活化的生物偶联反应，作为一种温和、无试剂的策略，将寡核苷酸连接到金表面。苯胺修饰的 DNA 与使用外加电位氧化成邻醌的邻苯二酚涂层电极偶联。可以在几分钟内实现高水平的耦合。通过改变反应时间和潜在的儿茶酚含量，可以指定最终的 DNA 表面覆盖率。这种方法的优势通过内分泌干扰物双酚 A 的电化学检测以及通过 DNA 杂交在电极表面捕获活的非贴壁细胞得到证明。这种方法不仅改善了 DNA 与金属表面的附着，而且代表了生物分子与设备平台的位点特异性附着的新方向。