7-[2-(Diethylamino)ethoxy]-5-hydroxy-6-methoxy-2-(4-methoxyphenyl)chromen-4-one | 1087318-96-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 7-[2-(Diethylamino)ethoxy]-5-hydroxy-6-methoxy-2-(4-methoxyphenyl)chromen-4-one
• CAS: 1087318-96-4
• 化学式: C₂₃H₂₇NO₆
• 分子量: 413.47
• InChiKey: PSCYMPQUKYAEBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  柳穿鱼黄素 、 2-二乙氨基氯乙烷盐酸盐 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以80%的产率得到7-[2-(Diethylamino)ethoxy]-5-hydroxy-6-methoxy-2-(4-methoxyphenyl)chromen-4-one
  参考文献：
  名称：

  In vitro biological evaluation of novel 7-O-dialkylaminoalkyl cytotoxic pectolinarigenin derivatives against a panel of human cancer cell lines

  摘要：

  The effect of novel pectolinarigenin derivatives bearing a dialkylaminoalkyl substituent at O-7 on cell proliferation was evaluated in vitro in a panel of seven human cancer cell lines including renal adenocarcinoma ACHN, amelanotic melanoma C32, colorectal adenocarcinoma Caco-2, lung large cell carcinoma COR-L23, malignant melanoma A375, lung carcinoma A549 and hepatocellular carcinoma Huh-7D12 cell lines. Pectolinarigenin (2), obtained by hydrolysis of rutinose unit of the pectolinarin (1) isolated from Linaria reflexa, exhibited cytotoxic activity against Caco-2, A549 and A375 cell lines with IC50 values of 5.3-8.2 mu M. The most active pectolinarigenin derivative was 3 characterized by a dimethylamino-propoxy group in O-7 with IC50 values of 7.2 and 7.4 mu M against COR-L23 and A549 cell lines, respectively. A structure-activity relationship analysis of synthesized compounds was performed. None of the tested compounds affected the proliferation of skin. broblasts 142BR suggesting a selective activity against tumor cells. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.037

文献信息

• In vitro biological evaluation of novel 7-O-dialkylaminoalkyl cytotoxic pectolinarigenin derivatives against a panel of human cancer cell lines
  作者：Marco Bonesi、Rosa Tundis、Brigitte Deguin、Monica R. Loizzo、Federica Menichini、François Tillequin、Francesco Menichini

  DOI：10.1016/j.bmcl.2008.09.037

  日期：2008.10

  The effect of novel pectolinarigenin derivatives bearing a dialkylaminoalkyl substituent at O-7 on cell proliferation was evaluated in vitro in a panel of seven human cancer cell lines including renal adenocarcinoma ACHN, amelanotic melanoma C32, colorectal adenocarcinoma Caco-2, lung large cell carcinoma COR-L23, malignant melanoma A375, lung carcinoma A549 and hepatocellular carcinoma Huh-7D12 cell lines. Pectolinarigenin (2), obtained by hydrolysis of rutinose unit of the pectolinarin (1) isolated from Linaria reflexa, exhibited cytotoxic activity against Caco-2, A549 and A375 cell lines with IC50 values of 5.3-8.2 mu M. The most active pectolinarigenin derivative was 3 characterized by a dimethylamino-propoxy group in O-7 with IC50 values of 7.2 and 7.4 mu M against COR-L23 and A549 cell lines, respectively. A structure-activity relationship analysis of synthesized compounds was performed. None of the tested compounds affected the proliferation of skin. broblasts 142BR suggesting a selective activity against tumor cells. (C) 2008 Elsevier Ltd. All rights reserved.