7-O-prenyl-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-prenyl-4-phenylcoumarin
• 英文别名: 7-[(3-methyl-2-butenyl)oxy]-4-phenyl-2H-chromen-2-one；7-(3-methylbut-2-enoxy)-4-phenylchromen-2-one
• 化学式: C₂₀H₁₈O₃
• mdl: MFCD01545426
• 分子量: 306.361
• InChiKey: ABLWAGJMSKIPNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-O-prenyl-4-phenylcoumarin 以77%的产率得到
  参考文献：
  名称：

  AHUJA M.; BANDOPADHYAY M.; SESHADRI T. R., INDIAN J. CHEM. , 1974 12, NO 3, 292-294

  摘要：

  DOI：
• 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-prenyl-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

• Structure–activity relationship of natural and synthetic coumarins inhibiting the multidrug transporter P-glycoprotein
  作者：Imad Raad、Raphael Terreux、Pascal Richomme、Eva-Laure Matera、Charles Dumontet、Jean Raynaud、David Guilet

  DOI：10.1016/j.bmc.2006.06.026

  日期：2006.10

  A set of 32 natural and synthetic coumarins were tested in order to evaluate their activity on human leukemic cells (K562/R7) overexpressing P-glycoprotein (P-gp). Their ability to reduce the P-gp-mediated drug efflux of daunorubicin out of cells was evaluated at 10 mu M. Four natural compounds, previously isolated from Calophyllum dispar (Clusiaceae) and substituted by a common alpha-(hydroxyisopropyl)dihydrofuran moiety, exhibited a significant inhibitory effect on P-gp when compared to the positive control cyclosporin A. A 3D-quantitative structure-activity relationship (3D-QSAR) analysis of the coumarins was performed using the biological results obtained by comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) of P-gp. Results showed a favorable electrostatic and steric volume, like the alpha-(hydroxyisopropyl)dihydrofuran moiety, beside C-5-C-6 or C-7-C-8 positions. In addition, the analysis revealed an important hydrophobic, neutral charge group, like phenyl, in position C-4 on the coumarinic ring. (c) 2006 Elsevier Ltd. All rights reserved.
• 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.
• AHUJA M.; BANDOPADHYAY M.; SESHADRI T. R., INDIAN J. CHEM. <IJOC-AP>, 1974 12, NO 3, 292-294
  作者：AHUJA M.、 BANDOPADHYAY M.、 SESHADRI T. R.

  DOI：——

  日期：——