7-hydroxy-4-(4-hydroxyphenyl)-3-phenyl-2H-chromen-2-one | 33257-75-9

• 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-4-(4-hydroxyphenyl)-3-phenyl-2H-chromen-2-one
• 英文别名: 3-Phenyl-4-(4-hydroxyphenyl)-7-hydroxycumarin；7-hydroxy-4-(4-hydroxy-phenyl)-3-phenyl-chromen-2-one；7-Hydroxy-4-(4-hydroxyphenyl)-3-phenylchromen-2-one
• CAS: 33257-75-9
• 化学式: C₂₁H₁₄O₄
• 分子量: 330.34
• InChiKey: PCZYJRSUQWHIOD-UHFFFAOYSA-N

物化性质

• 沸点：
  586.1±50.0 °C(Predicted)
• 密度：
  1.386±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 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：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-hydroxy-4-(4-hydroxyphenyl)-3-phenyl-2H-chromen-2-one 在 potassium carbonate 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 1.0h， 生成 7-(2-(diethylamino)ethoxy)-4-(4-(2-(diethylamino)ethoxy)phenyl)-3-phenyl-2Hchromen-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：

  4-(7-acetoxy-2-oxo-3-phenyl-2H-chromen-4-yl)phenyl acetate 在 盐酸 、 水 作用下， 以 丙酮 为溶剂， 以99%的产率得到7-hydroxy-4-(4-hydroxyphenyl)-3-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

文献信息

• [EN] FLAVONES AND COUMARINS AS AGENTS FOR THE TREATMENT OF ATHEROSCLEROSIS<br/>[FR] FLAVONES ET COUMARINES UTILISEES EN TANT QU'AGENTS DANS LE TRAITEMENT DE L'ATHEROSCLEROSE
  申请人：——

  公开号：WO1996031206A2

  公开（公告）日：1996-10-10

  [EN] Flavones and coumarins or a pharmaceutically acceptable salt thereof are inhibitors of VCAM-1 and ICAM-1 and are thus useful in the treatment of atherosclerosis, restenosis, and immune disorders such as arthritis and transplant rejection.
  [FR] Les flavones et les coumarines ou leurs sels pharmaceutiquement acceptables sont des inhibiteurs de VCAM-1 et ICAM-1 et sont donc utiles dans le traitement de l'athérosclérose, de la resténose et de troubles immunitaires tels que l'arthrite et le rejet des transplantations.
• 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.