乙基2-(6-乙氧基-3-氧代-3H-氧杂蒽-9-基)苯甲酸酯 | 87569-96-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 乙基2-(6-乙氧基-3-氧代-3H-氧杂蒽-9-基)苯甲酸酯
• 中文别名: 2-乙氧基-5-(4,5-二氢-3-十七烷基-5-羰基-1H-吡唑-1-基)苯磺基酸
• 英文名称: diethyl fluorescein
• 英文别名: ethoxyfluorescein ethyl ester；ethyl 2-(3-ethoxy-6-oxoxanthen-9-yl)benzoate
• CAS: 87569-96-8
• 化学式: C₂₄H₂₀O₅
• 分子量: 388.42
• InChiKey: FRUHKPFGFOXNQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  乙基2-(6-乙氧基-3-氧代-3H-氧杂蒽-9-基)苯甲酸酯 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以92%的产率得到ethoxyfluorescein hydrazide
  参考文献：
  名称：

  Fluorescein hydrazones: A series of novel non-intercalative topoisomerase IIα catalytic inhibitors induce G1 arrest and apoptosis in breast and colon cancer cells

  摘要：

  Fluorescein hydrazones (5 and 7) were synthesized in three/four steps with 82-92% yields. All synthesized compounds were evaluated by topoisomerase I (topo I) and topoisomerase II alpha (topo II alpha)mediated relaxation and cell viability assays. Among them, most of the compounds showed topo I & II alpha inhibitory activity and nineteen compounds showed strong anti-proliferative activity against various cell lines. In brief, 5e inhibited 53% topo II alpha (etoposide 29%) at 20 mu M and showed excellent antiproliferative activity against DU145 (1.43 +/- 0.04 mu M), HCT15 (2.4 +/- 0.03 mu M) and MCF7 (11.4 +/- 0.5 mu M) cell lines in comparison with adriamycin, etoposide, and camptothecin. Compounds 5e, 5g and 5h were further evaluated to determine their mode of action. Compounds 5e, 5g and 5h functioned as non-intercalative topo II alpha catalytic inhibitor with induction of G1 arrest and activation of apoptotic proteins in dose dependent manner. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.09.004
• 作为产物：
  描述：

  阿司匹林杂质G 生成 乙基2-(6-乙氧基-3-氧代-3H-氧杂蒽-9-基)苯甲酸酯
  参考文献：
  名称：

  Baeyer, Justus Liebigs Annalen der Chemie, 1876, vol. 183, p. 31

  摘要：

  DOI：

文献信息

• Fluorescence turn-on detection of hypochlorous acid via HOCl-promoted dihydrofluorescein-ether oxidation and its application in vivo
  作者：Yi Zhou、Ju-Ying Li、Kai-Hui Chu、Ke Liu、Cheng Yao、Jing-Yun Li

  DOI：10.1039/c2cc30265a

  日期：——

  We report three new water-soluble dihydrofluorescein-ether probes FCN1, FCN2 and FCN3 for the detection of hypochlorous acid (HOCl), which were designed on the basis of a specific HOCl-promoted oxidation reaction. This work also provided a useful method to monitor the accumulated HOCl in specific organelles using a zebrafish model.

  我们报告了三种新型水溶性二氟荧光素醚探针 FCN1、FCN2 和 FCN3，用于检测亚氯酸（HOCl），这些探针是基于特定的 HOCl 促进氧化反应设计的。本研究还提供了一种有用的方法，通过斑马鱼模型监测特定细胞器中累积的 HOCl。
• Synthesis and Photophysical Properties of Fluorescein Esters as Potential Organic Semiconductor Materials
  作者：Gamal A. E. Mostafa、Abu Syed Mahajumi、Haitham AlRabiah、Adnan A. Kadi、Yang Lu、A. F. M. Motiur Rahman

  DOI：10.1007/s10895-021-02789-y

  日期：2021.9

  photophysical properties, was esterified to have fluorescein ethyl ester (2) and O-ethyl-fluorescein ethyl ester (3) in excellent yields. All of them were investigated for the photophysical and electrochemical properties as potential organic semiconductor materials. Absorptions and emission spectra were taken in various solvents, compound 2 showed emission maxima at λmax = 545 and compound 3 showed λmax = 550 nm

  荧光素 ( 1 ) 是一种在显微镜下具有高光物理特性的已知荧光示踪剂，经酯化得到荧光素乙酯 ( 2 ) 和O-乙基-荧光素乙酯 ( 3 )，收率极好。所有这些都被研究作为潜在的有机半导体材料的光物理和电化学性能。在各种溶剂中获取吸收和发射光谱，化合物2在 λ max  = 545处显示发射最大值，化合物3显示 λ max  = 550 nm。光学带隙能量 ( E g ) 计算为1–3并且发现值在 2.34 – 2.39 eV 之间。研究了在各种 pH (5-9) 缓冲液中移动发射最大值的可能性，最后使用差示扫描量热法 (DSC) 和热重分析 (TGA) 检查热稳定性。通过1-3 的HOMO 和 LUMO 分布研究了2和3共轭系统的增加。实验结果表明，化合物2和3具有优异的光物理和电化学性能，可作为优良的有机半导体材料。
• Nietzki; Schroeter, Chemische Berichte, 1895, vol. 28, p. 52
  作者：Nietzki、Schroeter

  DOI：——

  日期：——
• Acree; Slagle, American Chemical Journal, 1909, vol. 42, p. 131
  作者：Acree、Slagle

  DOI：——

  日期：——