5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-(4-chlorophenyl)-3,4-dihydropyrimidin-2(1H)-thione | 1373886-17-9

• 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-chlorophenyl)-3,4-dihydropyrimidin-2(1H)-thione
• 英文别名: (E)-1-[4-(4-chlorophenyl)-6-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-2-sulfanylidene-3,4-dihydro-1H-pyrimidin-5-yl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one
• CAS: 1373886-17-9
• 化学式: C₂₉H₂₅ClN₂O₅S
• 分子量: 549.047
• InChiKey: OYNORKKMCBSNBN-PYEOWPDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  38
• 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：
  132
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  姜黄素 、 4-氯苯甲醛 、 硫脲 在 phosphomolybdic acid 作用下， 以 乙醇 为溶剂， 反应 0.04h， 以96%的产率得到5-(4-hydroxy-3-methoxyphenylethylenecarbonyl)-6-(4-hydroxy-3-methoxyphenylethylene)-4-(4-chlorophenyl)-3,4-dihydropyrimidin-2(1H)-thione
  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

• 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.
• Green synthesis, antioxidant and antibacterial activities of 4-aryl-3,4-dihydropyrimidinones/thiones derivatives of curcumin. Theoretical calculations and mechanism study
  作者：Nassima Khaldi-Khellafi、Malika Makhloufi-Chebli、Djamila Oukacha-Hikem、Souhila Terachet Bouaziz、Kamilia Ould Lamara、Taous Idir、Amina Benazzouz-Touami、Françoise Dumas

  DOI：10.1016/j.molstruc.2018.12.104

  日期：2019.4

  All the synthesized curcumin derivatives 4a–n were screened for antioxidant and antimicrobial activity. Biological activity data of the synthesized showed that most of the synthesized compounds exhibited greater antioxidant and antibacterial activity than curcumin. Geometries of synthesized compounds were optimized by using B3LYP method with 6-31G* basis set. Then, DFT based reactivity descriptors such

  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、