2-hydroxy-3-methyl-5-[(E)-3-(4-methylphenyl)-3-oxoprop-1-enyl]benzaldehyde | 1342894-77-2

• 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-(4-methylphenyl)-3-oxoprop-1-enyl]benzaldehyde
• CAS: 1342894-77-2
• 化学式: C₁₈H₁₆O₃
• 分子量: 280.323
• InChiKey: NXYIVYRPBGVGRK-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-二甲氧基苯乙酸 、 2-hydroxy-3-methyl-5-[(E)-3-(4-methylphenyl)-3-oxoprop-1-enyl]benzaldehyde 在 N-甲基吗啉 、 三聚氯氰 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以89%的产率得到(E)-3-(3,4-dimethoxyphenyl)-8-methyl-6-(3-oxo-3-p-tolylprop-1-enyl)-2H-chromen-2-one
  参考文献：
  名称：

  用氰尿酰氯高效合成3-芳基香豆素

  摘要：

  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。

  DOI：

  10.1055/s-0031-1290344
• 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 为溶剂， 反应 5.0h， 生成 2-hydroxy-3-methyl-5-[(E)-3-(4-methylphenyl)-3-oxoprop-1-enyl]benzaldehyde
  参考文献：
  名称：

  In vitro and in vivo antifilarial activity evaluation of 3,6-epoxy [1,5]dioxocines: A new class of antifilarial agents

  摘要：

  A series of 3,6-epoxy [1,5] dioxocines were synthesized and evaluated for their antifilarial activity against adult parasites of human lymphatic filarial parasite Brugia malayi (sub-periodic strain) in vitro. Out of these, six compounds (4a-f) possessed improved in vitro anti-filarial activity and examples 4d and 4f were also found to be active in the in vivo experiments. These results demonstrate that 3,6-epoxy [1,5] dioxocines exhibits potent antifilarial activity and might be developed into a new class of antifilarial drug. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.009

文献信息

• Antiplasmodial activity of novel keto-enamine chalcone-chloroquine based hybrid pharmacophores
  作者：Koneni V. Sashidhara、Manoj Kumar、Ram K. Modukuri、Rajeev Kumar Srivastava、Awakash Soni、Kumkum Srivastava、Shiv Vardan Singh、J.K. Saxena、Harsh M. Gauniyal、Sunil K. Puri

  DOI：10.1016/j.bmc.2012.03.011

  日期：2012.5

  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.
• Synthesis and antifilarial activity of chalcone–thiazole derivatives against a human lymphatic filarial parasite, Brugia malayi
  作者：Koneni V. Sashidhara、K. Bhaskara Rao、Vikas Kushwaha、Ram K. Modukuri、Richa Verma、P.K. Murthy

  DOI：10.1016/j.ejmech.2014.05.029

  日期：2014.6

  Here we report the synthesis of novel chalcone thiazole compounds and their antifilarial activity. The antifilarial properties of these hybrids were assessed against microfilariae as well as adult worms of Brugia malayi. Among all the synthesized compounds, only two compounds, namely 4g and 4n were identified to be promising in vitro. These active compounds were tested in B. malayi-jird (Meriones unguiculatus) and B. malayi-Mastomys coucha models. Compound 4n showed 100% embryostatic effect and 49% macrofilaricidal in jirds and M. coucha models, respectively. This study provides a new structural clue for the development of novel antifilarial lead molecules. (C) 2014 Elsevier Masson SAS. All rights reserved.