Ethyl 4-(4-hydroxyphenyl)-6-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: Ethyl 4-(4-hydroxyphenyl)-6-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: ethyl 4-(4-hydroxyphenyl)-6-phenyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate
• 化学式: C₁₉H₁₈N₂O₃S
• 分子量: 354.43
• InChiKey: VMTZTUACQAJLGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  103
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 4-(4-hydroxyphenyl)-6-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 在 sodium acetate 、 溶剂黄146 、 β-丙氨酸 作用下， 以 乙酸酐 、 溶剂黄146 为溶剂， 反应 7.0h， 生成 3-(5-((6-(ethoxycarbonyl)-5-(4-hydroxyphenyl)-3-oxo-7-phenyl-3,5-dihydro-2H-thiazolo[3,2-a]pyrimidin-2-ylidene)methyl)furan-2-yl)benzoic acid
  参考文献：
  名称：

  Biological evaluation of halogenated thiazolo[3,2-a]pyrimidin-3-one carboxylic acid derivatives targeting the YycG histidine kinase

  摘要：

  With an intention to potent inhibitors of YycG histidine kinase, a series of halogenated thiazolo[3,2-a]pyrimidin-3-one carboxylic acid derivatives were synthesized and evaluated for their antibacterial, antibiofilm and hemolytic activities. The majority of the compounds showed good activity against Staphylococcus epidermidis and Staphylococcus aureus, with MIC values of 1.56-6.25 mu M, simultaneously presented promising antiobifilm activity against S. epidermidis ATCC35984 at 50 mu M. The test of inhibitory activity on YycG kinase suggested the antibacterial activities of these derivatives are based on inhibiting the enzyme activity of the YycG HK domain. The hemolytic activity test suggested these compounds exhibited in vitro antibacterial activity at non-hemolytic concentrations. (c) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.096
• 作为产物：
  描述：

  苯甲酰乙酸乙酯 、 对羟基苯甲醛 、 硫脲 在 cerium(III) chloride heptahydrate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 Ethyl 4-(4-hydroxyphenyl)-6-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  Biological evaluation of halogenated thiazolo[3,2-a]pyrimidin-3-one carboxylic acid derivatives targeting the YycG histidine kinase

  摘要：

  With an intention to potent inhibitors of YycG histidine kinase, a series of halogenated thiazolo[3,2-a]pyrimidin-3-one carboxylic acid derivatives were synthesized and evaluated for their antibacterial, antibiofilm and hemolytic activities. The majority of the compounds showed good activity against Staphylococcus epidermidis and Staphylococcus aureus, with MIC values of 1.56-6.25 mu M, simultaneously presented promising antiobifilm activity against S. epidermidis ATCC35984 at 50 mu M. The test of inhibitory activity on YycG kinase suggested the antibacterial activities of these derivatives are based on inhibiting the enzyme activity of the YycG HK domain. The hemolytic activity test suggested these compounds exhibited in vitro antibacterial activity at non-hemolytic concentrations. (c) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.096

文献信息

• Design, synthesis and chemoinformatic studies of new thiazolopyrimidine derivatives as potent anticancer agents via phosphodiesterase-5 inhibition and apoptotic inducing activity
  作者：Mohamed T.M. Nemr、Mohamed Teleb、Asmaa M. AboulMagd、Mostafa E. El-Naggar、Noha Gouda、A.A. Abdel-Ghany、Yaseen A.M.M. Elshaier

  DOI：10.1016/j.molstruc.2022.134216

  日期：2023.1

  respectively in comparison to sildenafil (IC50 0.689 nM). Moreover, compounds 3a, 3c, 3f, 3g, 3h were found to have potent cytotoxic activities against MCF-7 cancer cell line with IC50 ranging from 5.47±0.4 to 9.92±0.9 µM. Apoptosis cytometric assay showed that compound 5a induced pronounced increase in the total percent of apoptotic HCT116 cells (15.87%) compared to 3c (12.43%), mainly during late stage

  抑制磷酸二酯酶 5 (PDE5) 已被证实为可能的癌症新治疗方法。为了进一步探索这一概念，设计并合成了三个系列的含有噻唑并嘧啶的化合物作为 PDE5 抑制剂。除了对三种不同癌细胞系（结肠直肠癌结肠癌；HCT-116，乳腺乳腺癌；MCF-7 和人前列腺癌；PC3）的抗增殖活性外，还评估了所有化合物对 PDE5 的抑制作用。细胞系（人肺成纤维细胞；WI38）。在合成的化合物中，三种化合物（3c、4a 和 5a）显着抑制 PDE5，IC 50分别为 0.046 nM、0.323 nM 和 0.546 nM，与西地那非（IC 500.689 纳米）。此外，化合物3a、3c、3f、3g、3h对 MCF-7 癌细胞系具有有效的细胞毒活性，IC 50范围为 5.47±0.4 至 9.92±0.9 µM。细胞凋亡细胞计数分析表明，与3c (12.43%) 相比，化合物5a诱导的凋亡 HCT116 细胞的总百分比