(E)-3-(3-(4-hydroxyphenyl)-3-oxoprop-1-enyl)-5-methoxy-4H-chromen-4-one | 1422452-47-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (E)-3-(3-(4-hydroxyphenyl)-3-oxoprop-1-enyl)-5-methoxy-4H-chromen-4-one
• 英文别名: 3-[(E)-3-(4-hydroxyphenyl)-3-oxoprop-1-enyl]-5-methoxychromen-4-one
• CAS: 1422452-47-8
• 化学式: C₁₉H₁₄O₅
• 分子量: 322.317
• InChiKey: IEYPLMKMSZZRSV-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-3-(3-(4-hydroxyphenyl)-3-oxoprop-1-enyl)-5-methoxy-4H-chromen-4-one 在 cerium(III) chloride heptahydrate 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.17h， 以44.8%的产率得到(E)-3-(3-hydroxy-3-(4-hydroxyphenyl)prop-1-enyl)-5-methoxy-4H-chromen-4-one
  参考文献：
  名称：

  Identification of novel chromenone derivatives as interleukin-5 inhibitors

  摘要：

  A series of (E)-5-alkoxy-3-(3-phenyl-3-oxoprop-1-enyl)-4H-chromen-4-ones (4) and (E)-5-alkoxy-3-(3-hydroxy-3-phenylprop-1-enyl)-4H-chromen-4-ones (5) were synthesized and evaluated for their IL-5 inhibitory activity. Propenone analogs 4 possess some of the structurally important characteristics of isoflavone 2 and chalcone 3 previously known as potent IL-5 inhibitor. However, the inhibitory activity of 4 was weak and therefore this structural hybridization appears to be ineffective for the design of IL-5 inhibitor. Meanwhile the potent activity profile of compounds 5 was discovered. This enhanced activity of 5 compared to 4 could be due to the effective location of hydroxyl group of allylic alcohol moiety of 5 in the 3D structure. The electron withdrawing substituents at position 4 of phenyl ring of 5 enhances the activity possibly due to an increase in the strength of hydrogen bonding property of hydroxyl group of allylic alcohol moiety. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.11.007
• 作为产物：
  描述：

  5-methoxyl-4-oxo-<1>benzopyran-3-carboxaldehyde 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (E)-3-(3-(4-hydroxyphenyl)-3-oxoprop-1-enyl)-5-methoxy-4H-chromen-4-one
  参考文献：
  名称：

  Identification of novel chromenone derivatives as interleukin-5 inhibitors

  摘要：

  A series of (E)-5-alkoxy-3-(3-phenyl-3-oxoprop-1-enyl)-4H-chromen-4-ones (4) and (E)-5-alkoxy-3-(3-hydroxy-3-phenylprop-1-enyl)-4H-chromen-4-ones (5) were synthesized and evaluated for their IL-5 inhibitory activity. Propenone analogs 4 possess some of the structurally important characteristics of isoflavone 2 and chalcone 3 previously known as potent IL-5 inhibitor. However, the inhibitory activity of 4 was weak and therefore this structural hybridization appears to be ineffective for the design of IL-5 inhibitor. Meanwhile the potent activity profile of compounds 5 was discovered. This enhanced activity of 5 compared to 4 could be due to the effective location of hydroxyl group of allylic alcohol moiety of 5 in the 3D structure. The electron withdrawing substituents at position 4 of phenyl ring of 5 enhances the activity possibly due to an increase in the strength of hydrogen bonding property of hydroxyl group of allylic alcohol moiety. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.11.007

文献信息

• Identification of novel chromenone derivatives as interleukin-5 inhibitors
  作者：Eeda Venkateswararao、Min-Seok Kim、Vinay K. Sharma、Ki-Cheul Lee、Santhosh Subramanian、Eunmiri Roh、Youngsoo Kim、Sang-Hun Jung

  DOI：10.1016/j.ejmech.2012.11.007

  日期：2013.1

  A series of (E)-5-alkoxy-3-(3-phenyl-3-oxoprop-1-enyl)-4H-chromen-4-ones (4) and (E)-5-alkoxy-3-(3-hydroxy-3-phenylprop-1-enyl)-4H-chromen-4-ones (5) were synthesized and evaluated for their IL-5 inhibitory activity. Propenone analogs 4 possess some of the structurally important characteristics of isoflavone 2 and chalcone 3 previously known as potent IL-5 inhibitor. However, the inhibitory activity of 4 was weak and therefore this structural hybridization appears to be ineffective for the design of IL-5 inhibitor. Meanwhile the potent activity profile of compounds 5 was discovered. This enhanced activity of 5 compared to 4 could be due to the effective location of hydroxyl group of allylic alcohol moiety of 5 in the 3D structure. The electron withdrawing substituents at position 4 of phenyl ring of 5 enhances the activity possibly due to an increase in the strength of hydrogen bonding property of hydroxyl group of allylic alcohol moiety. (C) 2012 Elsevier Masson SAS. All rights reserved.