2-(8-甲氧基苯并[e][1]苯并呋喃-1-基)乙酸 | 861820-86-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 中文名称: 2-(8-甲氧基苯并[e][1]苯并呋喃-1-基)乙酸
• 英文名称: 2-(8-methoxynaphtho[2,1-b]furan-1-yl)ethanoic acid
• 英文别名: 8-methoxy-naphtho[2,1-b]furan-1-yl acetic acid；2-(8-methoxynaphtho[2,1-b]furan-1-yl)acetic acid；(8-Methoxynaphtho[2,1-b]furan-1-yl)acetic acid；2-(8-methoxybenzo[e][1]benzofuran-1-yl)acetic acid
• CAS: 861820-86-2
• 化学式: C₁₅H₁₂O₄
• 分子量: 256.258
• InChiKey: YRVGZJSMDISESG-UHFFFAOYSA-N

物化性质

• 熔点：
  176.8-178.9 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  466.4±30.0 °C(Predicted)
• 密度：
  1.335±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(8-甲氧基苯并[e][1]苯并呋喃-1-基)乙酸 在 sodium hydroxide 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 N-[2-(8-methoxynaphtho[2,1-b]furan-1-yl)-acetyl]-(L)-phenylalanine
  参考文献：
  名称：

  Carboxylic fused furans for amino acid fluorescent labelling

  摘要：

  Four carboxylic fused furans are presented as new fluorescent labels for the amino and hydroxyl functions of organic molecules. Various representative L-amino acids were chosen as models, labelled at their N-terminus and also at their side-chain. Fluorescent derivatives were obtained in high yields, and their absorption and emission properties were studied. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.07.003
• 作为产物：
  描述：

  7-甲氧基-2-萘 在 sodium hydroxide 作用下， 以 硫酸 为溶剂， 反应 68.0h， 生成 2-(8-甲氧基苯并[e][1]苯并呋喃-1-基)乙酸
  参考文献：
  名称：

  萘并[2,1- b ]呋喃作为新的荧光标记：合成和光谱表征

  摘要：

  为了评估其作为生物分子的荧光标记和在肽合成中的适用性，由氧代苯并吡喃通过碱环收缩并在其N末端或侧链官能团上与各种l-氨基酸偶联，合成了一种荧光萘呋喃。收集所有衍生物的荧光数据，发现它们是中等荧光的并且具有中等至良好的荧光量子产率。

  DOI：

  10.1016/j.tetlet.2005.05.035

文献信息

• A naphtho[2,1-b]furan as a new fluorescent label: synthesis and spectral characterisation
  作者：Ana M. Piloto、Susana P.G. Costa、M. Sameiro T. Gonçalves

  DOI：10.1016/j.tetlet.2005.05.035

  日期：2005.7

  contraction and coupled with various l-amino acids at their N-terminus or at side-chain functional groups, in order to evaluate its applicability as a fluorescent label for biomolecules and in peptide synthesis. Fluorescence data were collected for all derivatives, which were found to be moderately fluorescent and having moderate to good fluorescence quantum yields.

  为了评估其作为生物分子的荧光标记和在肽合成中的适用性，由氧代苯并吡喃通过碱环收缩并在其N末端或侧链官能团上与各种l-氨基酸偶联，合成了一种荧光萘呋喃。收集所有衍生物的荧光数据，发现它们是中等荧光的并且具有中等至良好的荧光量子产率。
• Carboxylic fused furans for amino acid fluorescent labelling
  作者：Ana M. Piloto、Andrea S.C. Fonseca、Susana P.G. Costa、M. Sameiro T. Gonçalves

  DOI：10.1016/j.tet.2006.07.003

  日期：2006.9

  Four carboxylic fused furans are presented as new fluorescent labels for the amino and hydroxyl functions of organic molecules. Various representative L-amino acids were chosen as models, labelled at their N-terminus and also at their side-chain. Fluorescent derivatives were obtained in high yields, and their absorption and emission properties were studied. (c) 2006 Elsevier Ltd. All rights reserved.
• Design and synthesis of tailored human caseinolytic protease P inhibitors
  作者：Thomas F. Gronauer、Melanie M. Mandl、Markus Lakemeyer、Mathias W. Hackl、Martina Meßner、Vadim S. Korotkov、Johanna Pachmayr、Stephan A. Sieber

  DOI：10.1039/c8cc05265d

  日期：——

  Human caseinolytic protease P (hClpP) is important for degradation of misfolded proteins in the mitochondrial unfolded protein response. We here introduce tailored hClpP inhibitors that utilize a steric discrimination in their core naphthofuran scaffold to selectively address the human enzyme. This novel inhibitor generation exhibited superior activity compared to previously introduced beta-lactones

  人类酪蛋白水解蛋白酶P（hClpP）对于线粒体未折叠蛋白质反应中错误折叠的蛋白质的降解非常重要。我们在这里介绍经过定制的hClpP抑制剂，这些抑制剂在其核心萘呋喃支架中利用空间识别来选择性地处理人的酶。与以前引入的针对细菌ClpP优化的β-内酯相比，这种新的抑制剂产生具有更高的活性。通过化学蛋白质组学以及癌细胞中的增殖和迁移研究，获得了对生物活性和与细胞靶标结合的进一步了解。