7-acetonyl-11-methoxy-6-oxo-6H,7H-(1)benzopyrano[4,3-b]-(1)benzopyran | 1030296-03-7

• 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: 7-acetonyl-11-methoxy-6-oxo-6H,7H-(1)benzopyrano[4,3-b]-(1)benzopyran
• 英文别名: 11-methoxy-7-(2-oxopropyl)-7H-chromeno[3,2-c]chromen-6-one
• CAS: 1030296-03-7
• 化学式: C₂₀H₁₆O₅
• 分子量: 336.344
• InChiKey: WEVWZHAGNTXSNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-羟基香豆素 、 8-甲氧基-3-乙酰基香豆素 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 60.0h， 以7%的产率得到7-acetonyl-11-methoxy-6-oxo-6H,7H-(1)benzopyrano[4,3-b]-(1)benzopyran
  参考文献：
  名称：

  Synthesis, computational study and cytotoxic activity of new 4-hydroxycoumarin derivatives

  摘要：

  Six new 4-hydroxycoumarin derivatives have been synthesized. They were characterized by UV-vis, IR, (1)H NMR, (13)C NMR, mass spectral data, elemental analysis, TLC and melting point determination. The new 4-hydroxycoumarin derivatives are studied by computational methods DFT (B3LYP) and force field methods (MM2 and OPLS), in order to optimize their geometry and calculate quantum-chemical properties and conformational analysis. Five new 4-hydroxycoumarin derivatives were tested for cytotoxic activity in two tumor cell lines - HL-60 and EL The obtained results are compared with the utilized anticancer drug melphalan. Two of these compounds - ethyl 2-[(3,4-dihydroxyphenyl)-(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]-3-oxobutanoate (SS-16) and ethyl 2-[(4-hydroxy-2-oxo-2H-chromen-3-yl)(3-nitrophenyl)methyl]-3-oxobutanoate (SS-21) show comparatively good cytotoxic properties. Their activity is weaker than melphalan. SS-16 seems to be more active than SS-21. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.05.005

文献信息

• Synthesis, computational study and cytotoxic activity of new 4-hydroxycoumarin derivatives
  作者：Stancho Stanchev、Georgi Momekov、Frank Jensen、Ilia Manolov

  DOI：10.1016/j.ejmech.2007.05.005

  日期：2008.4

  Six new 4-hydroxycoumarin derivatives have been synthesized. They were characterized by UV-vis, IR, (1)H NMR, (13)C NMR, mass spectral data, elemental analysis, TLC and melting point determination. The new 4-hydroxycoumarin derivatives are studied by computational methods DFT (B3LYP) and force field methods (MM2 and OPLS), in order to optimize their geometry and calculate quantum-chemical properties and conformational analysis. Five new 4-hydroxycoumarin derivatives were tested for cytotoxic activity in two tumor cell lines - HL-60 and EL The obtained results are compared with the utilized anticancer drug melphalan. Two of these compounds - ethyl 2-[(3,4-dihydroxyphenyl)-(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]-3-oxobutanoate (SS-16) and ethyl 2-[(4-hydroxy-2-oxo-2H-chromen-3-yl)(3-nitrophenyl)methyl]-3-oxobutanoate (SS-21) show comparatively good cytotoxic properties. Their activity is weaker than melphalan. SS-16 seems to be more active than SS-21. (c) 2007 Elsevier Masson SAS. All rights reserved.