4,6-bis((E)-4-hydroxy-3-methoxystyryl)pyrimidine-2(1H)-thione | 1196995-43-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4,6-bis((E)-4-hydroxy-3-methoxystyryl)pyrimidine-2(1H)-thione
• 英文别名: 4,6-bis[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-1H-pyrimidine-2-thione
• CAS: 1196995-43-3
• 化学式: C₂₂H₂₀N₂O₄S
• 分子量: 408.478
• InChiKey: XOIRSCJVZSIOKJ-FCXRPNKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-(4-((1Z,3E)-2-hydroxy-4-(4-hydroxy-3-methoxyphenyl)buta-1,3-dien-1-yl)-2-imino-5,6-dihydro-2H-1,3-thiazin-6-yl)-2-methoxyphenol 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以56%的产率得到4,6-bis((E)-4-hydroxy-3-methoxystyryl)pyrimidine-2(1H)-thione
  参考文献：
  名称：

  Design and synthesis of novel iminothiazinylbutadienols and divinylpyrimidinethiones as ARE inducers

  摘要：

  Novel iminothiazinylbutadienols and divinylpyrimidinethiones were designed and synthesized as analogues of curcumin with its diketone moiety masked as a heterocyclic adduct with thiourea. The chemical stability of these novel heterocyclic compounds was improved as compared to curcumin. They exhibit longer half-lives and do not react with nucleophilic thiols under physiological conditions. In an ARE-luciferase reporter assay, some of these new curcumin analogues are more effective ARE activators than curcumin and isothiocyanates. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.072

文献信息

• In-silico designing, chemical synthesis, characterization and in-vitro assessment of antibacterial properties of some analogues of curcumin
  作者：Manoj K. Shrivash、Sonali Mishra、UpmaNarain、Jyoti Pandey、Krishna Misra

  DOI：10.1016/j.micpath.2018.06.030

  日期：2018.10

  Caulobacter vibrioides (similar to Pseudomonas aeruginosa) and Pyruvate kinase of Staphylococcus aureus were docked with curcumin, the wonder molecule from the spice turmeric and structures of its twelve analogues were designed, synthesized and tested in-vitro for antibacterial activity. Based on the test results a comparative account of the probable mechanism has been given Two major alternative targets are

  在目前的工作中，两个关键的调节蛋白，即弧菌的单体MipZ（类似于铜绿假单胞菌）和金黄色葡萄球菌的丙酮酸激酶与姜黄素对接，设计，合成和测试了来自香料姜黄的奇异分子及其结构的十二种类似物。体外具有抗菌活性。根据测试结果，对可能的机理进行了比较说明，为药物分子的抗菌活性提供了两个主要的替代目标。这些可能是细菌细胞壁脂质或负责细菌细胞平滑功能的蛋白质。在前一种情况下，由于革兰氏阳性细菌和革兰氏阴性细菌细胞壁结构的显着差异，因此不可能确定相同的配体会同时影响两者。商业药物多数是抗革兰氏阴性菌，而在目前的工作中，我们发现了最有效的革兰氏阳性菌药物。根据测试结果，给出了可能机制的比较说明。显然，与细胞壁破坏机制一起，其他并行机制也起作用。
• Conversion of Curcumin into Heterocyclic Compounds as Potent Anti-diabetic and Anti-histamine Agents
  作者：Sara Nabil、Soheir N. Abd El-Rahman、Suhailah S. Al-Jameel、Asma M. Elsharif

  DOI：10.1248/bpb.b18-00170

  日期：2018.7.1

  Potential biologically active derivatives of the curcumin were prepared by the cyclocondensation reaction cyclohexanone 2, imino pyrimidine 3, pyrmidinones 4, thiopyrimidine 6 and pyranone 5, 7 when treated with acetylacetone, guanidine, ureaethylcyanoacetate, thiourea and ethylacetoacetate, respectively. The structures of compounds (2–7) were elucidated by means of microanalysis as well as spectral measurements such as IR, 1H-NMR, MS. The anti-diabetic potential of curcumin derivatives were evaluated by assessing amylase inhibition assay, also inhibition of histamine release activity of curcumin derivatives were assessed by U937 human monocytes. The results for amylase inhibition activity revels that the curcumin inhibits α-amylase in a concentration dependent manner. Compounds 4 and 5 exhibited significant inhibitory activity against amylase enzyme and was comparable with that of acrabose. Also, compounds 5, 6 and 7 exhibited significant inhibitory activity against histamine. Our results concluded that curcumin pyrmidinones and pyranone derivatives have highly effects as anti-diabetic and anti-histamine activities.

  环己酮 2、亚氨基嘧啶 3、吡啶酮 4、硫代嘧啶 6 和吡喃酮 5、7 分别与乙酰丙酮、胍、氰基乙酸脲乙酯、硫脲和乙酰乙酸乙酯发生环缩合反应，制备了姜黄素的潜在生物活性衍生物。化合物（2-7）的结构通过显微分析以及红外光谱、1H-NMR、质谱等光谱测量得以阐明。通过淀粉酶抑制实验评估了姜黄素衍生物的抗糖尿病潜力，还用 U937 人单核细胞评估了姜黄素衍生物对组胺释放活性的抑制作用。淀粉酶抑制活性的结果表明，姜黄素对α-淀粉酶的抑制作用呈浓度依赖性。化合物 4 和 5 对淀粉酶具有明显的抑制活性，与阿卡波糖的抑制活性相当。此外，化合物 5、6 和 7 对组胺也有明显的抑制作用。我们的研究结果表明，姜黄素吡啶酮和吡喃酮衍生物具有很强的抗糖尿病和抗组胺活性。