2',6'-dihydroxydihydrochalcone-4'-O-β-D-glucopyranoside | 73519-16-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2',6'-dihydroxydihydrochalcone-4'-O-β-D-glucopyranoside
• 英文别名: 1-Propanone, 1-[4-(beta-D-glucopyranosyloxy)-2,6-dihydroxyphenyl]-3-phenyl-；1-[2,6-dihydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3-phenylpropan-1-one
• CAS: 73519-16-1
• 化学式: C₂₁H₂₄O₉
• 分子量: 420.416
• InChiKey: PDEJQNUGODFPTR-QNDFHXLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  157
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 2',6'-dihydroxydihydrochalcone-4'-O-β-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 16.0h， 以6.8 mg的产率得到Acetic acid 3-acetoxy-2-(3-phenyl-propionyl)-5-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl ester
  参考文献：
  名称：

  Antileishmanial activities of dihydrochalcones from piper elongatum and synthetic related compounds. Structural requirements for activity

  摘要：

  Two dihydrochalcones (1 and 2) were isolated from Piper elongatum Vahl by activity-guided fractionation against extracellular promastigotes of Leishmania braziliensis in vitro. Their structures were elucidated by spectral analysis, including homonuclear and heteronuclear correlation NMR experiments. Derivatives 3-7 and 20 synthetic related compounds (8-27) were also assayed to establish the structural requirements for antileishmanial activity. Compounds 1-11 that proved to be more active that ketoconazol, used as positive control, were further assayed against promastigotes of Leishmania tropica and Leishmania infantum. Compounds 7 and 11, with a C-6-C-3-C-6 System, proved to be the most promising compounds, with IC50 values of 2.98 and 3.65 mug/mL, respectively, and exhibited no toxic effect on macrophages (around 90% viability). Correlation between the molecular structures and antileishmanial activity is discussed in detail. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00406-1

文献信息

• Antileishmanial activities of dihydrochalcones from piper elongatum and synthetic related compounds. Structural requirements for activity
  作者：Alicia Hermoso、Ignacio A Jiménez、Zulma A Mamani、Isabel L Bazzocchi、José E Piñero、Angel G Ravelo、Basilio Valladares

  DOI：10.1016/s0968-0896(03)00406-1

  日期：2003.9

  Two dihydrochalcones (1 and 2) were isolated from Piper elongatum Vahl by activity-guided fractionation against extracellular promastigotes of Leishmania braziliensis in vitro. Their structures were elucidated by spectral analysis, including homonuclear and heteronuclear correlation NMR experiments. Derivatives 3-7 and 20 synthetic related compounds (8-27) were also assayed to establish the structural requirements for antileishmanial activity. Compounds 1-11 that proved to be more active that ketoconazol, used as positive control, were further assayed against promastigotes of Leishmania tropica and Leishmania infantum. Compounds 7 and 11, with a C-6-C-3-C-6 System, proved to be the most promising compounds, with IC50 values of 2.98 and 3.65 mug/mL, respectively, and exhibited no toxic effect on macrophages (around 90% viability). Correlation between the molecular structures and antileishmanial activity is discussed in detail. (C) 2003 Elsevier Ltd. All rights reserved.