5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-phenyl-3,4-dihydropyrimidin-2(1H)-one | 1373886-08-8

• 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-phenyl-3,4-dihydropyrimidin-2(1H)-one
• 英文别名: 4-phenyl-3,4-dihydropyrimidine-2(1H)-one curcumin；6-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-5-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]-4-phenyl-3,4-dihydro-1H-pyrimidin-2-one
• CAS: 1373886-08-8
• 化学式: C₂₉H₂₆N₂O₆
• 分子量: 498.535
• InChiKey: WLPPNHGMOSPRES-HRVWGNOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  117
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  姜黄素 、 苯甲醛 、 尿素 在 phosphomolybdic acid 作用下， 以 乙醇 为溶剂， 反应 0.04h， 以97%的产率得到5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-phenyl-3,4-dihydropyrimidin-2(1H)-one
  参考文献：
  名称：

  姜黄素 4-芳基-3,4-二氢嘧啶酮/硫酮衍生物的绿色合成、抗氧化和抗菌活性。理论计算与机理研究

  摘要：

  摘要 使用姜黄素、取代的芳香醛和尿素/硫脲，在较少体积的乙醇催化下，通过一锅多组分环缩合反应，以良好的收率合成了姜黄素的 3,4-二氢嘧啶-2(1H)-酮/硫酮类似物。商业杂多酸 Keggin 型 H3PMo12O40 5% mol 作为在常规加热和微波辐射下可回收且无毒的催化剂。筛选了所有合成的姜黄素衍生物 4a-n 的抗氧化和抗菌活性。合成的生物活性数据表明，大多数合成的化合物表现出比姜黄素更高的抗氧化和抗菌活性。使用B3LYP方法以6-31G*基组优化合成化合物的几何形状。然后，基于 DFT 的反应性描述符，例如 HOMO、LUMO、化学硬度、电负性、

  DOI：

  10.1016/j.molstruc.2018.12.104

文献信息

• 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。
• Design, structure activity relationship, cytotoxicity and evaluation of antioxidant activity of curcumin derivatives/analogues
  作者：Pramod K. Sahu

  DOI：10.1016/j.ejmech.2016.05.037

  日期：2016.10

  better cytotoxicity effect against three cell lines. According to results of SAR study, it was found that 3,4-dihydropyrimidines of curcumin, 2c, 2d, 2j and 2n exhibited better antioxidant activity than curcumin. A correlation of structure and activities relationship of these compounds with respect to drug score profiles and other physico-chemical properties of drugs are described and verified experimentally

  设计，合成了新的14种姜黄素3,4-二氢嘧啶衍生物/类似物（2a - 2n），并对它们的细胞毒性和抗氧化活性进行了生物学评估。已经通过MTT测定法评估了针对三种细胞系HeLa，HCT-116和QG-56的细胞毒性作用。从SAR研究中发现，特别是化合物2e和2j（IC 50值为12.5μM）对三种细胞系表现出更好的细胞毒性作用。根据SAR研究的结果，发现姜黄素的3,4-二氢嘧啶，2c，2d，2j和2n表现出比姜黄素更好的抗氧化活性。这些化合物的结构和活性关系与药物得分曲线和药物的其他理化性质之间的相关性已得到描述和实验验证。因此，我们得出的结论是，理化分析可以证明姜黄素类似物的结构特征及其有前途的联合细胞毒性/抗氧化活性，并且还可以通过虚拟和实际筛选得出结论，这些化合物具有广泛的亲脂性，记录P值。
• 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.