5-Hydroxy-6-methoxy-2-(4-methoxyphenyl)-7-(2-morpholin-4-ylethoxy)chromen-4-one | 1087319-02-5

• 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: 5-Hydroxy-6-methoxy-2-(4-methoxyphenyl)-7-(2-morpholin-4-ylethoxy)chromen-4-one
• CAS: 1087319-02-5
• 化学式: C₂₃H₂₅NO₇
• 分子量: 427.454
• InChiKey: ZSZWQKNERKRAOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  86.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  柳穿鱼黄素 、 N-(2-氯乙基)吗啉盐酸盐 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以82%的产率得到5-Hydroxy-6-methoxy-2-(4-methoxyphenyl)-7-(2-morpholin-4-ylethoxy)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.