7-hydroxy-3,4-bis(4-hydroxyphenyl)-2H-chromen-2-one | 1450604-28-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 7-hydroxy-3,4-bis(4-hydroxyphenyl)-2H-chromen-2-one
• 英文别名: 7-Hydroxy-3,4-bis(4-hydroxyphenyl)chromen-2-one；7-hydroxy-3,4-bis(4-hydroxyphenyl)chromen-2-one
• CAS: 1450604-28-0
• 化学式: C₂₁H₁₄O₅
• 分子量: 346.339
• InChiKey: WZWSRVMGMGNMOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-hydroxy-3,4-bis(4-hydroxyphenyl)-2H-chromen-2-one 、 1,2-二溴乙烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 0.5h， 以69%的产率得到7-(2-bromoethoxy)-3,4-bis(4-(2-bromoethoxy)phenyl)-2H-chromen-2-one
  参考文献：
  名称：

  Design, synthesis, and anti-tumor activities of novel triphenylethylene–coumarin hybrids, and their interactions with Ct-DNA

  摘要：

  Novel triphenylethylene-coumarin hybrid derivatives containing different amounts of amino side chains Were designed and synthesized in good yields under microwave radiation. The derivatives 5b-d which possessed two amino side chains (except morpholinyl) showed a broad-spectrum and good anti-proliferative activity against five tumor cells and low cytotoxicity in osteoblast. UV-vis, fluorescence, and circular dichroism (CD) spectroscopies and thermal denaturation exhibited that compounds 10c, 5c, and 13c bearing amino side chain (except morpholinyl) on 4-phenyl had significant interactions with Ct-DNA by the intercalative mode of binding. Structure-activity relationships (SARs) analysis suggested that the amino alkyl chain would play an important role both in the compounds against tumor cells proliferation and their interactions with DNA. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.07.009
• 作为产物：
  描述：

  (2-hydroxy-4-methoxyphenyl)-(4-hydroxyphenyl)-methanone 在 盐酸 、 水 、 三乙胺 作用下， 以 丙酮 为溶剂， 反应 0.5h， 生成 7-hydroxy-3,4-bis(4-hydroxyphenyl)-2H-chromen-2-one
  参考文献：
  名称：

  Design, synthesis, and anti-tumor activities of novel triphenylethylene–coumarin hybrids, and their interactions with Ct-DNA

  摘要：

  Novel triphenylethylene-coumarin hybrid derivatives containing different amounts of amino side chains Were designed and synthesized in good yields under microwave radiation. The derivatives 5b-d which possessed two amino side chains (except morpholinyl) showed a broad-spectrum and good anti-proliferative activity against five tumor cells and low cytotoxicity in osteoblast. UV-vis, fluorescence, and circular dichroism (CD) spectroscopies and thermal denaturation exhibited that compounds 10c, 5c, and 13c bearing amino side chain (except morpholinyl) on 4-phenyl had significant interactions with Ct-DNA by the intercalative mode of binding. Structure-activity relationships (SARs) analysis suggested that the amino alkyl chain would play an important role both in the compounds against tumor cells proliferation and their interactions with DNA. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.07.009

文献信息

• Dual functional small molecule fluorescent probes for image-guided estrogen receptor-specific targeting coupled potent antiproliferative potency for breast cancer therapy
  作者：Lu Yang、Zhiye Hu、Junjie Luo、Chu Tang、Silong Zhang、Wentao Ning、Chune Dong、Jian Huang、Xianjun Liu、Hai-Bing Zhou

  DOI：10.1016/j.bmc.2017.05.002

  日期：2017.7

  A strategy by integrating biological imaging into early stages of the drug discovery process can improve our understanding of drug activity during preclinical and clinical study. In this article, we designed and synthesized coumarin-based nonsteroidal type fluorescence ligands for drug-target binding imaging. Among these synthesized compounds, 3e, 3f and 3h showed potent ER binding affinity and 3e (IC50 = 0.012 mu M) exhibited excellent ERo: antagonistic activity, its antiproliferative potency in breast cancer MCF-7 cells is equipotent to the approved drug tamoxifen. The fluorescence of compounds 3e and 3f depended on the solvent properties and showed significant changes when mixed with Elta or ER/3 in vitro. Furthermore, target molecule 3e could cross the cell membrane, localize and image drug-target interaction in real time without cell washing. Thus, the coumarin-based platform represents a promising new ER-targeted delivery vehicle with potential imaging and therapeutic properties. (C) 2017 Elsevier Ltd. All rights reserved.
• Design, synthesis, and anti-tumor activities of novel triphenylethylene–coumarin hybrids, and their interactions with Ct-DNA
  作者：Hua Chen、Shuai Li、Yuchao Yao、Likai Zhou、Jianpeng Zhao、Yunjing Gu、Kerang Wang、Xiaoliu Li

  DOI：10.1016/j.bmcl.2013.07.009

  日期：2013.9

  Novel triphenylethylene-coumarin hybrid derivatives containing different amounts of amino side chains Were designed and synthesized in good yields under microwave radiation. The derivatives 5b-d which possessed two amino side chains (except morpholinyl) showed a broad-spectrum and good anti-proliferative activity against five tumor cells and low cytotoxicity in osteoblast. UV-vis, fluorescence, and circular dichroism (CD) spectroscopies and thermal denaturation exhibited that compounds 10c, 5c, and 13c bearing amino side chain (except morpholinyl) on 4-phenyl had significant interactions with Ct-DNA by the intercalative mode of binding. Structure-activity relationships (SARs) analysis suggested that the amino alkyl chain would play an important role both in the compounds against tumor cells proliferation and their interactions with DNA. (C) 2013 Elsevier Ltd. All rights reserved.