1-(2-hydroxyphenyl)-3-[4-(methoxymethoxy)phenyl]prop-2-en-1-one | 569316-60-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(2-hydroxyphenyl)-3-[4-(methoxymethoxy)phenyl]prop-2-en-1-one
• 英文别名: 1-(2-Hydroxyphenyl)-3-[4-(methoxymethoxy)phenyl]prop-2-en-1-one
• CAS: 569316-60-5
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: ZRBPUHYIFVQKOE-UHFFFAOYSA-N

物化性质

• 沸点：
  476.6±45.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxyphenyl)-3-[4-(methoxymethoxy)phenyl]prop-2-en-1-one 在 Tl(NO₃)2*3H₂O 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以51.3%的产率得到3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
  参考文献：
  名称：

  Structural requirement of isoflavonones for the inhibitory activity of interleukin-5

  摘要：

  Sophoricoside isolated from Sophora japonica is a glycoside of isoflavonone as an inhibitor of interleukin (IL)-5. To identify structural requirements of this isoflavonone for its inhibitory activity against IL-5, isoflavonones, isoflavanones, and their glycosides were prepared and their inhibitory activity was tested against IL-5. Among them, 5-benzyloxy-3-(4-hydroxyphenyl)chromen-4-one (4b, 87.9% inhibition at 50 muM, IC50 = 15.3 muM) shows the most potent activity, comparable with that of sophoricoside. The important structural requirements of these isoflavonone analogs exhibiting the inhibitory activity against IL-5 were recognized as (1) planarity of chromen-4-one ring, (2) existence of phenolic hydroxyl at 4-position of B ring, and (3) introduction of benzyloxy at 5-position, which may act as a bulky group for occupying hydrophobic pocket in putative binding site. However the glucopyranosyl moiety of sophoricoside is not an essential motif for the activity. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(03)00064-3
• 作为产物：
  描述：

  4-methoxymethoxy-benzaldehyde 、 2'-羟基苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以78%的产率得到1-(2-hydroxyphenyl)-3-[4-(methoxymethoxy)phenyl]prop-2-en-1-one
  参考文献：
  名称：

  Structural requirement of isoflavonones for the inhibitory activity of interleukin-5

  摘要：

  Sophoricoside isolated from Sophora japonica is a glycoside of isoflavonone as an inhibitor of interleukin (IL)-5. To identify structural requirements of this isoflavonone for its inhibitory activity against IL-5, isoflavonones, isoflavanones, and their glycosides were prepared and their inhibitory activity was tested against IL-5. Among them, 5-benzyloxy-3-(4-hydroxyphenyl)chromen-4-one (4b, 87.9% inhibition at 50 muM, IC50 = 15.3 muM) shows the most potent activity, comparable with that of sophoricoside. The important structural requirements of these isoflavonone analogs exhibiting the inhibitory activity against IL-5 were recognized as (1) planarity of chromen-4-one ring, (2) existence of phenolic hydroxyl at 4-position of B ring, and (3) introduction of benzyloxy at 5-position, which may act as a bulky group for occupying hydrophobic pocket in putative binding site. However the glucopyranosyl moiety of sophoricoside is not an essential motif for the activity. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(03)00064-3

文献信息

• Structural requirement of isoflavonones for the inhibitory activity of interleukin-5
  作者：Sang-Hun Jung、Soo-Hyun Cho、The Hung Dang、Jee-Hyun Lee、Jung-Hun Ju、Mi-Kyung Kim、Seung-Ho Lee、Jae-Chun Ryu、Youngsoo Kim

  DOI：10.1016/s0223-5234(03)00064-3

  日期：2003.5

  Sophoricoside isolated from Sophora japonica is a glycoside of isoflavonone as an inhibitor of interleukin (IL)-5. To identify structural requirements of this isoflavonone for its inhibitory activity against IL-5, isoflavonones, isoflavanones, and their glycosides were prepared and their inhibitory activity was tested against IL-5. Among them, 5-benzyloxy-3-(4-hydroxyphenyl)chromen-4-one (4b, 87.9% inhibition at 50 muM, IC50 = 15.3 muM) shows the most potent activity, comparable with that of sophoricoside. The important structural requirements of these isoflavonone analogs exhibiting the inhibitory activity against IL-5 were recognized as (1) planarity of chromen-4-one ring, (2) existence of phenolic hydroxyl at 4-position of B ring, and (3) introduction of benzyloxy at 5-position, which may act as a bulky group for occupying hydrophobic pocket in putative binding site. However the glucopyranosyl moiety of sophoricoside is not an essential motif for the activity. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.