7-O-butanoyl-4-phenylcoumarin

• 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-O-butanoyl-4-phenylcoumarin
• 英文别名: 2-oxo-4-phenyl-2H-chromen-7-yl butanoate；(2-oxo-4-phenylchromen-7-yl) butanoate
• 化学式: C₁₉H₁₆O₄
• mdl: MFCD02071956
• 分子量: 308.334
• InChiKey: JJKXPKJVQBEWSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯甲酰乙酸乙酯 在 高氯酸 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 1.5h， 生成 7-O-butanoyl-4-phenylcoumarin
  参考文献：
  名称：

  Synthesis and in vitro evaluation of leishmanicidal activity of 7-hydroxy-4-phenylcoumarin derivatives

  摘要：

  Eight coumarin derivatives (2-8) were synthesized from 7-hydroxy-4-phenylcoumarin 1 and were evaluated for their in vitro leishmanicidal activity against promastigote and amastigote forms of Leishmania amazonensis, as well their toxicity in murine macrophages. Compounds 4 and 7 showed the most significant results against promastigote forms of L. amazonensis. They were at least three-fold more active than 1 and Compound 4 was as effective as Amphotericin B. Compound 4, a 7-O-prenylated derivative, and 7, a tetra- O -acetyl-beta- D -glucopyranosyl derivative, presented IC50 values of 21.35 and 10.03 A mu M against promastigote and IC50 values of 58.10 and 34.93 A mu M, respectively against amastigote forms. Furthermore, they do not cause toxicity in mammalian or Leishmania cells in vitro. This study shows that these coumarin derivatives are potential prototypes for the development of novel drugs with leishmanicidal activity.

  DOI：

  10.1007/s00044-016-1729-1

文献信息

• Synthesis and in vitro evaluation of leishmanicidal activity of 7-hydroxy-4-phenylcoumarin derivatives
  作者：Isael A. Rosa、Letícia de Almeida、Karina F. Alves、Marcos J. Marques、Antônio M. Fregnan、Claudinei A. Silva、Juliana O. S. Giacoppo、Teodorico C. Ramalho、Diogo T. Carvalho、Marcelo H. dos Santos

  DOI：10.1007/s00044-016-1729-1

  日期：2017.1

  Eight coumarin derivatives (2-8) were synthesized from 7-hydroxy-4-phenylcoumarin 1 and were evaluated for their in vitro leishmanicidal activity against promastigote and amastigote forms of Leishmania amazonensis, as well their toxicity in murine macrophages. Compounds 4 and 7 showed the most significant results against promastigote forms of L. amazonensis. They were at least three-fold more active than 1 and Compound 4 was as effective as Amphotericin B. Compound 4, a 7-O-prenylated derivative, and 7, a tetra- O -acetyl-beta- D -glucopyranosyl derivative, presented IC50 values of 21.35 and 10.03 A mu M against promastigote and IC50 values of 58.10 and 34.93 A mu M, respectively against amastigote forms. Furthermore, they do not cause toxicity in mammalian or Leishmania cells in vitro. This study shows that these coumarin derivatives are potential prototypes for the development of novel drugs with leishmanicidal activity.