2-(2-benzoyl-β-D-glucopyranosyloxy)-7-(1α,2α,6α-trihydroxy-3-oxocyclohex-4-enoyl)-5-hydroxybenzyl alcohol | 1425057-06-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-benzoyl-β-D-glucopyranosyloxy)-7-(1α,2α,6α-trihydroxy-3-oxocyclohex-4-enoyl)-5-hydroxybenzyl alcohol
• 英文别名: [2-[(2S,3R,4S,5S,6R)-3-benzoyloxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxyphenyl]methyl (1R,2R,6R)-1,2,6-trihydroxy-5-oxocyclohex-3-ene-1-carboxylate
• CAS: 1425057-06-2
• 化学式: C₂₇H₂₈O₁₄
• 分子量: 576.511
• InChiKey: DLBOMVFEFWKKHS-MUZBHQQFSA-N

物化性质

• 沸点：
  874.3±65.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  230
• 氢给体数：
  7
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  2-(2-benzoyl-β-D-glucopyranosyloxy)-7-(1α,2α,6α-trihydroxy-3-oxocyclohex-4-enoyl)-5-hydroxybenzyl alcohol 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 生成 可得然胶
  参考文献：
  名称：

  Isolation and identification of β-hematin inhibitors from Flacourtia indica as promising antiplasmodial agents

  摘要：

  An ethanolic extract (A001) of the leaves and twigs of Flacourtia indica (Burm.f.) Merr, was purified to give a new phenolic glycoside, 2-(2-benzoyl-beta-D-glucopyranosyloxy)-7-(1 alpha,2 alpha,6 alpha-trihydroxy-3-oxocyclohex4-enoyl)-5-hydroxybenzyl alcohol (1) together with poliothrysoside (2), catechin-15,6-e]-4 beta-(3,4-dihydroxyphenyl)dihydro-2(3H)-pyranone (3), 2-(6-benzoyl-beta-D-glucopyranosyloxy)-7-(1 alpha,2 alpha,6 alpha-trihydroxy-3-oxocyclohex-4-enoyl)-5-hydroxybenzyl alcohol (4), chrysoeriol-7-O-beta-D-glucopyranoside (5), and mururin A (6). Compound 6 significantly inhibited the in vitro growth of both a chloroquine-sensitive (3D7) and a chloroquine-resistant (K1) strain of Plasmodium falciparum. It forms a complex with hematin and inhibits beta-hematin formation, suggesting that this compound act on a heme polymerization target. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.12.019