ethyl [N-(2-fluoroacridonyl)]acetate | 116897-24-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: ethyl [N-(2-fluoroacridonyl)]acetate
• 英文别名: ethyl‑2‑(2‑fluoro‑9‑oxoacridin‑10(9H)‑yl)acetate；Ethyl 2-(2-fluoro-9-oxoacridin-10-yl)acetate
• CAS: 116897-24-6
• 化学式: C₁₇H₁₄FNO₃
• 分子量: 299.301
• InChiKey: IOHSIVBXVSLEHL-UHFFFAOYSA-N

物化性质

• 熔点：
  185-187 °C(Solv: ethanol (64-17-5))
• 沸点：
  452.7±45.0 °C(Predicted)
• 密度：
  1.290±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl [N-(2-fluoroacridonyl)]acetate 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 2.5h， 生成 FAESC
  参考文献：
  名称：

  In vivo investigation of homocysteine metabolism to polyamines by high-resolution accurate mass spectrometry and stable isotope labeling

  摘要：

  Polyamines are essential polycations, playing important roles in mammalian physiology. Theoretically, the involvement of homocysteine in polyamine synthesis via S-adenosylmethionine is possible; however, to our knowledge, it has not been established experimentally. Here, we propose an original approach for investigation of homocysteine metabolites in an animal model. The method is based on the combination of isotope-labeled homocysteine supplementation and high-resolution accurate mass spectrometry analysis. Structural identity of the isotope-labeled metabolites was confirmed by accurate mass measurements of molecular and fragment ions and comparison of the retention times and tandem mass spectrometry fragmentation patterns. Isotope-labeled methionine, spermidine, and spermine were detected in all investigated plasma and tissue samples. The induction of moderate hyperhomocysteinemia leads to an alteration in polyamine levels in a different manner. The involvement of homocysteine in polyamine synthesis and modulation of polyamine levels could contribute to a better understanding of the mechanisms connected with homocysteine toxicity. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.ab.2014.04.007
• 作为产物：
  描述：

  2-fluoroacridin-9(10H)-one 、 溴乙酸乙酯 以 N,N-二甲基甲酰胺 为溶剂， 以54.5 %的产率得到ethyl [N-(2-fluoroacridonyl)]acetate
  参考文献：
  名称：

  Synthesis, cytotoxicity, and docking based analysis of acridone-N-acetamides as AKT kinase inhibitors

  摘要：

  本研究的主要目标是合成和表征吖啶酮的 N-取代乙酰氨基衍生物，其中乙酰氨基被认为是一种连接体，对多种生物活性（包括抗癌活性）至关重要。为此，研究人员评估了合成衍生物对人类乳腺癌（MCF-7、MDA-MB-231）、肺癌（A-549）和皮肤癌（A-431）细胞系的抗增殖活性。结果表明，化合物 8 h、8i、9 h 和 9i 对 MCF-7 细胞株表现出最强的活性，IC50 值分别为 13.96 µM、8.25 µM、9.45 µM 和 6.76 µM。此外，所有这些化合物对正常细胞（NIH/3T3）均无毒性。此外，AKT 激酶抑制实验结果表明，化合物 8i 和 9i 具有抑制 AKT 激酶的功效，具有潜在的抗癌活性。细胞周期分析表明，化合物 8i 和 9i 可阻滞细胞周期的 G0/G1 期，而与 CT-DNA 的吸收滴定则表明这些分子可与 DNA 发生相互作用。为了了解这些化合物的药物相似性，对所有化合物进行了不同的硅学筛选评估，结果表明这些化合物具有最佳的理化特性，是优秀的先导分子。最后，利用分子对接研究对体外结果进行了验证，发现了在 AKT 活性部位的结合相互作用。

  DOI：

  10.1007/s11696-023-02692-9

文献信息

• Szulc, Zdzislaw, Journal fur praktische Chemie (Leipzig 1954), 1987, vol. 329, # 4, p. 741 - 744
  作者：Szulc, Zdzislaw

  DOI：——

  日期：——
• SZULC, ZDZISLAW, J. PRAKT. CHEM., 329,(1987) N 4, 741-744
  作者：SZULC, ZDZISLAW

  DOI：——

  日期：——
• In vivo investigation of homocysteine metabolism to polyamines by high-resolution accurate mass spectrometry and stable isotope labeling
  作者：Silviya Ruseva、Valentin Lozanov、Petia Markova、Radoslav Girchev、Vanio Mitev

  DOI：10.1016/j.ab.2014.04.007

  日期：2014.7

  Polyamines are essential polycations, playing important roles in mammalian physiology. Theoretically, the involvement of homocysteine in polyamine synthesis via S-adenosylmethionine is possible; however, to our knowledge, it has not been established experimentally. Here, we propose an original approach for investigation of homocysteine metabolites in an animal model. The method is based on the combination of isotope-labeled homocysteine supplementation and high-resolution accurate mass spectrometry analysis. Structural identity of the isotope-labeled metabolites was confirmed by accurate mass measurements of molecular and fragment ions and comparison of the retention times and tandem mass spectrometry fragmentation patterns. Isotope-labeled methionine, spermidine, and spermine were detected in all investigated plasma and tissue samples. The induction of moderate hyperhomocysteinemia leads to an alteration in polyamine levels in a different manner. The involvement of homocysteine in polyamine synthesis and modulation of polyamine levels could contribute to a better understanding of the mechanisms connected with homocysteine toxicity. (C) 2014 Elsevier Inc. All rights reserved.