5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-(4-methoxyphenyl)-3,4-dihydropyrimidin-2(1H)-one | 1373886-11-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-(4-methoxyphenyl)-3,4-dihydropyrimidin-2(1H)-one
• 英文别名: 6-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-5-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]-4-(4-methoxyphenyl)-3,4-dihydro-1H-pyrimidin-2-one
• CAS: 1373886-11-3
• 化学式: C₃₀H₂₈N₂O₇
• 分子量: 528.562
• InChiKey: LYGUVARKYFATOM-CWUHIXJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  姜黄素 、 4-甲氧基苯甲醛 、 尿素 在 chitosan (viscosity 800–2000 cps) 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 1.33h， 以94%的产率得到5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-(4-methoxyphenyl)-3,4-dihydropyrimidin-2(1H)-one
  参考文献：
  名称：

  壳聚糖：一种高效的可生物降解和可回收的绿色催化剂，用于在水性介质中一锅合成姜黄素的3,4-二氢嘧啶酮

  摘要：

  姜黄素，芳族醛和脲/硫脲的简单一锅缩合反应已经开发出一种有效的姜黄素3,4-二氢嘧啶酮合成方法，该方法是在60°C的水性介质中，将壳聚糖在2％乙酸中存在持续80–90分钟。在反应中，姜黄素：一种潜在的生物活性分子已被用作使用壳聚糖作为有效的可生物降解和可循环利用的绿色催化剂的多组分合成的组分。形成的产物姜黄素3，4-二氢嘧啶酮产率极高（97％）。壳聚糖催化剂可以重复使用而不会损失催化活性。

  DOI：

  10.1016/j.catcom.2012.06.017

文献信息

• Design, synthesis, synergistic antimicrobial activity and cytotoxicity of 4-aryl substituted 3,4-dihydropyrimidinones of curcumin
  作者：Jaggi Lal、S.K. Gupta、D. Thavaselvam、D.D. Agarwal

  DOI：10.1016/j.bmcl.2012.02.056

  日期：2012.4

  3,4-Dihydropyrimidinones of curcumin were synthesized in excellent yield by multi-component one-pot condensation of curcumin, substituted aromatic aldehydes and urea/thiourea under solvent free conditions using SnCl2 center dot 2H(2)O catalyst. All the synthesized compounds have been characterized by IR, H-1 NMR, C-13 NMR, Mass spectra as well as elemental analyses. The synthesized compounds 4a-n were evaluated for their synergistic antimicrobial (antibacterial and antifungal) activity against bacteria and fungi. Zone of inhibition was measured by adopting disc diffusion method. In vitro minimum inhibitory concentrations were measured using broth microdilution and food poisoning method. In addition to this in vitro cytotoxicity of synthesized compounds against three human cancer lines Hep-G2, HCT-116 and QG-56 were also evaluated. Most of the compounds showed interesting antimicrobial and cytotoxic activity as compared to curcumin, that is, the compounds derived from 2-hydroxy benzaldehyde, 4-hydroxy benzaldehyde and 4-hydroxy-3-methoxy benzaldehyde showed the highest biological activity as compared to other compounds. (C) 2012 Elsevier Ltd. All rights reserved.
• Chitosan: An efficient biodegradable and recyclable green catalyst for one-pot synthesis of 3,4-dihydropyrimidinones of curcumin in aqueous media
  作者：Jaggi Lal、Sushil K. Gupta、Dau D. Agarwal

  DOI：10.1016/j.catcom.2012.06.017

  日期：2012.10

  multi-component synthesis using chitosan as an efficient biodegradable and recyclable green catalyst. The resultant product curcumin 3,4-dihydropyrimidinone is formed in excellent yield (97%). The chitosan catalyst can be reused for without loss of catalytic activity.

  姜黄素，芳族醛和脲/硫脲的简单一锅缩合反应已经开发出一种有效的姜黄素3,4-二氢嘧啶酮合成方法，该方法是在60°C的水性介质中，将壳聚糖在2％乙酸中存在持续80–90分钟。在反应中，姜黄素：一种潜在的生物活性分子已被用作使用壳聚糖作为有效的可生物降解和可循环利用的绿色催化剂的多组分合成的组分。形成的产物姜黄素3，4-二氢嘧啶酮产率极高（97％）。壳聚糖催化剂可以重复使用而不会损失催化活性。