2-hydroxy-3-methyl-5-[(E)-3-oxo-3-(3,4,5-trimethoxyphenyl)prop-1-enyl]benzaldehyde | 1373497-77-8

• 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: 2-hydroxy-3-methyl-5-[(E)-3-oxo-3-(3,4,5-trimethoxyphenyl)prop-1-enyl]benzaldehyde
• CAS: 1373497-77-8
• 化学式: C₂₀H₂₀O₆
• 分子量: 356.375
• InChiKey: CCGQVMNITJSRCV-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(2-氨基乙基)氨基-7-氯喹啉 、 2-hydroxy-3-methyl-5-[(E)-3-oxo-3-(3,4,5-trimethoxyphenyl)prop-1-enyl]benzaldehyde 以 乙醇 为溶剂， 反应 0.17h， 以87%的产率得到(E)-6-((2-(7-chloroquinolin-4-ylamino)ethylamino)methylene)-2-methyl-4-((E)-3-oxo-3-(3,4,5-trimethoxyphenyl)prop-1-enyl)cyclohexa-2,4-dienone
  参考文献：
  名称：

  Antiplasmodial activity of novel keto-enamine chalcone-chloroquine based hybrid pharmacophores

  摘要：

  A series of novel keto-enamine chalcone-chloroquine based hybrids were synthesized following new methodology developed in our laboratory. The synthesized compounds were screened against chloroquine sensitive strain (3D7) of Plasmodium falciparum in an in vitro model. Some of the compounds were showing comparable antimalarial activity at par with chloroquine. Compounds with significant in vitro antimalarial activity were then evaluated for their in vivo efficacy in Swiss mice against Plasmodium yoelii (chloroquine resistant N-67 strain), wherein compounds 25 and 27 each showed an in vivo suppression of 99.9% parasitaemia on day 4. Biochemical studies reveal that inhibition of hemozoin formation is the primary mechanism of action of these analogues. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.011
• 作为产物：
  描述：

  邻甲酚 在 盐酸 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 5.0h， 生成 2-hydroxy-3-methyl-5-[(E)-3-oxo-3-(3,4,5-trimethoxyphenyl)prop-1-enyl]benzaldehyde
  参考文献：
  名称：

  Antiplasmodial activity of novel keto-enamine chalcone-chloroquine based hybrid pharmacophores

  摘要：

  A series of novel keto-enamine chalcone-chloroquine based hybrids were synthesized following new methodology developed in our laboratory. The synthesized compounds were screened against chloroquine sensitive strain (3D7) of Plasmodium falciparum in an in vitro model. Some of the compounds were showing comparable antimalarial activity at par with chloroquine. Compounds with significant in vitro antimalarial activity were then evaluated for their in vivo efficacy in Swiss mice against Plasmodium yoelii (chloroquine resistant N-67 strain), wherein compounds 25 and 27 each showed an in vivo suppression of 99.9% parasitaemia on day 4. Biochemical studies reveal that inhibition of hemozoin formation is the primary mechanism of action of these analogues. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.011

文献信息

• Efficient and General Synthesis of 3-Aryl Coumarins Using Cyanuric Chloride¹
  作者：Koneni Sashidhara、Gopala Palnati、Srinivasa Avula、Abdhesh Kumar

  DOI：10.1055/s-0031-1290344

  日期：2012.3

  protocol for a rapid synthesis of different substituted 3-aryl coumarins is reported. A series of different substituted phenyl acetic acids have been successfully reacted with different substituted 2-hydroxy benzaldehydes in the presence of cyanuric chloride (2,4,6-trichloro-1,3,5-triazine) and N-methyl morpholine to afford 3-aryl coumarins in good to excellent yields. synthesis - 3-aryl coumarins -

  报道了快速合成不同取代的3-芳基香豆素的有效且通用的方案。在氰尿酰氯（2,4,6-三氯-1,3,5-三嗪）和N-甲基吗啉的存在下，一系列不同的取代苯基乙酸已成功与不同的取代的2-羟基苯甲醛反应，得到3芳基香豆素的收率高至优异。 合成-3-芳基香豆素-氰尿酰氯-2-羟基苯甲醛 系列“新型合成方法论研究”的第八部分。