ethyl 2-[(3,4-dimethyl-2-oxo-2H-chromen-7-yl)oxy]acetate | 35679-90-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: ethyl 2-[(3,4-dimethyl-2-oxo-2H-chromen-7-yl)oxy]acetate
• 英文别名: Acetic acid, [(3,4-dimethyl-2-oxo-2h-1-benzopyran-7-yl)oxy]-, ethyl ester；ethyl 2-(3,4-dimethyl-2-oxochromen-7-yl)oxyacetate
• CAS: 35679-90-4
• 化学式: C₁₅H₁₆O₅
• mdl: MFCD02080999
• 分子量: 276.289
• InChiKey: IKDRPWUBFBORSQ-UHFFFAOYSA-N

物化性质

• 沸点：
  420.3±45.0 °C(Predicted)
• 密度：
  1.200±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-[(3,4-dimethyl-2-oxo-2H-chromen-7-yl)oxy]acetate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 1-[2-(3,4-dimethyl-2-oxo-2H-1-benzopyran-7-yloxy)acetyl]-4-phenylthiosemicarbazide
  参考文献：
  名称：

  Synthesis, docking and in vitro anticancer evaluation of some new benzopyrone derivatives

  摘要：

  The synthesis of some new 3-alkyl-7-hydroxy-4-methyl-8-substituted-1H-benzopyran-2-ones, 6-alkyl-7-methyl-2-substituted amino-5H-pyrano[6,5-e] benzoxazol-5-ones, 7-alkyl-8-methyl-3-substituted-2,6-dihydropyrano[6,5-f]-1,4-benzoxazin-6-ones, 7,8-disubstituted-3-ethyl-4-methyl-1H-benzopyran-2-ones and 3-alkyl-4-methyl-7-substituted-1H-benzopyran-2-ones were described. Fourteen compounds were selected by National Cancer Institute (NCI), Bethesda, and evaluated for their in vitro anticancer activity in the full NCI 60 cell lines panel assay by a single dose test. Compounds 4a, 18a, 18b and 23a were found to be broad-spectrum antitumors showing effectiveness toward numerous cell lines that belong to different tumor subpanels. Furthermore, docking studies were undertaken to gain insight into the possible binding mode of these compounds with the binding site of the casein kinase II (CK2) enzyme which is involved in cell survival and proliferation through a number of downstream effectors. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2014.02.003
• 作为产物：
  描述：

  二甲基伞形酮 、 溴乙酸乙酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 5.0h， 以98%的产率得到ethyl 2-[(3,4-dimethyl-2-oxo-2H-chromen-7-yl)oxy]acetate
  参考文献：
  名称：

  2-氧代乙氧基香豆素的新便捷途径：天然产物合成中的关键中间体

  摘要：

  提出了一种从羟基香豆素开始合成香豆素氧基醛的新方法。这些化合物是制备天然产物（如geiparvarin和补骨脂素）中有用的中间体，现在可以通过简单的后处理程序以高收率获得。此外，所报道的途径已经应用于二羟基香豆素。

  DOI：

  10.1016/s0040-4020(02)00442-8

文献信息

• Coumarin-acetohydrazide derivatives as novel antiproliferative agents <i>via</i> VEGFR-2/AKT axis inhibition and apoptosis triggering
  作者：Lina M. A. Abdel Ghany、Nehad M. El-Dydamony、Amira A. Helwa、Sahar M. Abdelraouf、Rana M. Abdelnaby

  DOI：10.1039/d2nj02436e

  日期：——

  The VEGFR-2/AKT pathway is a crucial axis in tumor survival where it is highly dysregulated in many cancer types.

  血管内皮生长因子受体-2/AKT 通路是肿瘤生存的关键轴，在许多癌症类型中都存在高度失调。
• A new convenient route to 2-oxoethoxycoumarins: key intermediates in the synthesis of natural products
  作者：Stefano Chimichi、Marco Boccalini、Barbara Cosimelli

  DOI：10.1016/s0040-4020(02)00442-8

  日期：2002.6

  A new synthetic route to coumarinyloxyaldehydes starting from hydroxycoumarins is presented; these compounds, useful intermediates in the preparation of natural products such as geiparvarin and psoralens, are now available in excellent yields with a simple workup procedure. Moreover the reported route has been applied to dihydroxycoumarins.

  提出了一种从羟基香豆素开始合成香豆素氧基醛的新方法。这些化合物是制备天然产物（如geiparvarin和补骨脂素）中有用的中间体，现在可以通过简单的后处理程序以高收率获得。此外，所报道的途径已经应用于二羟基香豆素。
• Synthesis, docking and in vitro anticancer evaluation of some new benzopyrone derivatives
  作者：Sohair L. El-Ansary、Mohammed M. Hussein、Doaa E. Abdel Rahman、Lina M.A. Abdel Ghany

  DOI：10.1016/j.bioorg.2014.02.003

  日期：2014.4

  The synthesis of some new 3-alkyl-7-hydroxy-4-methyl-8-substituted-1H-benzopyran-2-ones, 6-alkyl-7-methyl-2-substituted amino-5H-pyrano[6,5-e] benzoxazol-5-ones, 7-alkyl-8-methyl-3-substituted-2,6-dihydropyrano[6,5-f]-1,4-benzoxazin-6-ones, 7,8-disubstituted-3-ethyl-4-methyl-1H-benzopyran-2-ones and 3-alkyl-4-methyl-7-substituted-1H-benzopyran-2-ones were described. Fourteen compounds were selected by National Cancer Institute (NCI), Bethesda, and evaluated for their in vitro anticancer activity in the full NCI 60 cell lines panel assay by a single dose test. Compounds 4a, 18a, 18b and 23a were found to be broad-spectrum antitumors showing effectiveness toward numerous cell lines that belong to different tumor subpanels. Furthermore, docking studies were undertaken to gain insight into the possible binding mode of these compounds with the binding site of the casein kinase II (CK2) enzyme which is involved in cell survival and proliferation through a number of downstream effectors. (C) 2014 Elsevier Inc. All rights reserved.

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