7-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-phenylchromen-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: 7-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-phenylchromen-2-one
• 英文别名: 7-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4-phenylcoumarin；4-phenyl-7-O-(β-D-tetraacetylglucopyranosyl)-2H-chromen-2-one；2-oxo-4-phenyl-2H-chromen-7-yl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(2-oxo-4-phenylchromen-7-yl)oxyoxan-2-yl]methyl acetate
• 化学式: C₂₉H₂₈O₁₂
• 分子量: 568.534
• InChiKey: QCLMGHOOPBXDPV-KRZJEZTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  150
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  7-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-phenylchromen-2-one 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以87%的产率得到7-O-(β-D-glucopyranosyl)-4-phenyl-2H-chromen-2-one
  参考文献：
  名称：

  Modified Coumarins. 19. Synthesis of Neoflavone D-Glycopyranosides

  摘要：

  新黄酮β-D-吡喃葡萄糖苷、β-D-吡喃半乳糖苷、β-D-吡喃木糖苷和α-D-吡喃阿拉伯糖苷是通过 7-羟基-4-芳基香豆素的钾盐与乙酰溴化糖的迈克尔缩合反应合成的，然后对生成的过乙酸酯进行脱乙酰化反应。

  DOI：

  10.1007/s10600-006-0007-8
• 作为产物：
  描述：

  间苯二酚 在 高氯酸 、 potassium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 反应 1.5h， 生成 7-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-phenylchromen-2-one
  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

• Modified Coumarins. 19. Synthesis of Neoflavone D-Glycopyranosides
  作者：Ya. L. Garazd、M. M. Garazd、V. P. Khilya

  DOI：10.1007/s10600-006-0007-8

  日期：2005.11

  Neoflavone β-D-glucopyranosides, β-D-galactopyranosides, β-D-xylopyranosides, and α-D-arabinopyranosides were synthesized by Michael condensation of potassium salts of 7-hydroxy-4-arylcoumarins with acetobromosugars followed by deacetylation of the resulting peracetates.

  新黄酮β-D-吡喃葡萄糖苷、β-D-吡喃半乳糖苷、β-D-吡喃木糖苷和α-D-吡喃阿拉伯糖苷是通过 7-羟基-4-芳基香豆素的钾盐与乙酰溴化糖的迈克尔缩合反应合成的，然后对生成的过乙酸酯进行脱乙酰化反应。
• Highly efficient glucosylation of flavonoids
  作者：Volodymyr Semeniuchenko、Yana Garazd、Myroslav Garazd、Tetyana Shokol、Ulrich Groth、Volodymyr Khilya

  DOI：10.1007/s00706-009-0207-6

  日期：2009.12

  A highly efficient procedure for glucosylation of flavonoids by acetobromoglucose is described. Glucosylation is carried out in a two-phase system CHCl3/H2O over 96 h using tetrabutylammonium bromide as phase-transfer catalyst. A purification procedure can be performed without column chromatography, and the yields of the glucosylated flavonoids are mostly quantitative. Acetylated glucosides were deprotected with sodium methanolate to afford the desired glucosides of flavonoids.
• 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.