3,4-bis(4-hydroxyphenyl)-2H-chromen-2-one

• 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: 3,4-bis(4-hydroxyphenyl)-2H-chromen-2-one
• 英文别名: 3,4-bis-(4-hydroxy-phenyl)-coumarin；3,4-Bis-(4-hydroxy-phenyl)-cumarin；3,4-Bis(4-hydroxyphenyl)chromen-2-one；3,4-bis(4-hydroxyphenyl)chromen-2-one
• 化学式: C₂₁H₁₄O₄
• 分子量: 330.34
• InChiKey: AAWIIFRBYZBHQO-UHFFFAOYSA-N

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：

  3,4-bis(4-hydroxyphenyl)-2H-chromen-2-one 、 N,N-二乙基氯乙胺 在 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 8.0h， 以55%的产率得到3,4-bis(4-(2-(diethylamino)ethoxy)phenyl)-2H-chromen-2-one
  参考文献：
  名称：

  Cytotoxicity and DNA binding property of triphenylethylene–coumarin hybrids with two amino side chains

  摘要：

  Novel triphenylethylene-coumarin hybrids containing two amino side chains were designed and synthesized. Some of these 3,4-diphenyl coumarins, 7b-c (the double chains at 4-position on 3-, 4-phenyl, respectively), and 13b-f (the double chains at 4-position on 3-phenyl and 7-position, respectively), 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 7b (R = piperidinyl), 7e (R = NEt2), and 7f (R = 4-methylpiperazinyl) had significant interactions with Ct-DNA by the intercalative mode of binding. Structure activity relationships (SARs) analysis suggested that the location of the two amino alkyl chains 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.2013.12.084
• 作为产物：
  描述：

  4-(4-(4-methoxyphenyl)-2-oxo-2H-chromen-3-yl)phenyl acetate 在 盐酸 、 水 、 三溴化硼 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 3,4-bis(4-hydroxyphenyl)-2H-chromen-2-one
  参考文献：
  名称：

  Cytotoxicity and DNA binding property of triphenylethylene–coumarin hybrids with two amino side chains

  摘要：

  Novel triphenylethylene-coumarin hybrids containing two amino side chains were designed and synthesized. Some of these 3,4-diphenyl coumarins, 7b-c (the double chains at 4-position on 3-, 4-phenyl, respectively), and 13b-f (the double chains at 4-position on 3-phenyl and 7-position, respectively), 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 7b (R = piperidinyl), 7e (R = NEt2), and 7f (R = 4-methylpiperazinyl) had significant interactions with Ct-DNA by the intercalative mode of binding. Structure activity relationships (SARs) analysis suggested that the location of the two amino alkyl chains 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.2013.12.084

文献信息

• Bz-HYDROXYLATED-3-ARYL- AND 3,4-DIARYL-COUMARINS
  作者：NG. PH. BUU-HOÏ、BERNARD EKERT、RENÉ ROYER

  DOI：10.1021/jo01374a020

  日期：1954.9