(E)-3-(4-hydroxy-3-methoxyphenyl)-1-[6-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-4-(4-methoxyphenyl)-2-sulfanylidene-3,4-dihydro-1H-pyrimidin-5-yl]prop-2-en-1-one | 1373886-19-1

• 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: (E)-3-(4-hydroxy-3-methoxyphenyl)-1-[6-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-4-(4-methoxyphenyl)-2-sulfanylidene-3,4-dihydro-1H-pyrimidin-5-yl]prop-2-en-1-one
• CAS: 1373886-19-1
• 化学式: C₃₀H₂₈N₂O₆S
• 分子量: 544.628
• InChiKey: BFLZZZGPFHBJEL-CWUHIXJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 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：
  141
• 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 、 硫脲 在 tin(II) chloride dihdyrate 作用下， 反应 1.33h， 以92%的产率得到(E)-3-(4-hydroxy-3-methoxyphenyl)-1-[6-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-4-(4-methoxyphenyl)-2-sulfanylidene-3,4-dihydro-1H-pyrimidin-5-yl]prop-2-en-1-one
  参考文献：
  名称：

  Design, synthesis, synergistic antimicrobial activity and cytotoxicity of 4-aryl substituted 3,4-dihydropyrimidinones of curcumin

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2012.02.056

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.