Ethyl 6-(1,3-benzodioxol-5-yl)-4-phenyl-2-sulfanyl-1,6-dihydropyrimidine-5-carboxylate | 301675-77-4

• 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 6-(1,3-benzodioxol-5-yl)-4-phenyl-2-sulfanyl-1,6-dihydropyrimidine-5-carboxylate
• 英文别名: ethyl 4-(1,3-benzodioxol-5-yl)-6-phenyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 301675-77-4
• 化学式: C₂₀H₁₈N₂O₄S
• 分子量: 382.44
• InChiKey: RYCRCHGBIHEQSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl 6-(1,3-benzodioxol-5-yl)-4-phenyl-2-sulfanyl-1,6-dihydropyrimidine-5-carboxylate 在 哌啶 、 sodium acetate 、 乙酸酐 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 10.0h， 生成 ethyl 5-(1,3-benzodioxol-5-yl)-2-[[4-(2-methoxy-2-oxoethoxy)phenyl]methylidene]-3-oxo-7-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
  参考文献：
  名称：

  Thiazolidione derivatives as novel antibiofilm agents: Design, synthesis, biological evaluation, and structure–activity relationships

  摘要：

  Rational designed novel thiazolidiones were synthesized and evaluated for antibiofilm activity. The active derivatives were not only potent inhibitors of Staphylococcus epidermidis biofilm growth but also efficient antibacterial agents. 3f showed 4-fold higher activity (6.25 mu M) in the biofilms dispersal assay and significantly higher antibacterial activity (MIC 3.125 mu M) in comparison to the 3-(5-((6- (ethoxycarbonyl)-5-(benzo[1,3]dioxol-5-yl)-3-oxo-7-phenyl- thiazolo[3,2-a]pyrimidin-2(5H)-ylidene)methyl) furan-2-yl)benzoic acid (1). (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.12.014
• 作为产物：
  描述：

  胡椒醛 、 苯甲酰乙酸乙酯 、 硫脲 在 tin(II) chloride dihydrate 作用下， 以 乙醇 为溶剂， 生成 Ethyl 6-(1,3-benzodioxol-5-yl)-4-phenyl-2-sulfanyl-1,6-dihydropyrimidine-5-carboxylate
  参考文献：
  名称：

  Thiazolidione derivatives as novel antibiofilm agents: Design, synthesis, biological evaluation, and structure–activity relationships

  摘要：

  Rational designed novel thiazolidiones were synthesized and evaluated for antibiofilm activity. The active derivatives were not only potent inhibitors of Staphylococcus epidermidis biofilm growth but also efficient antibacterial agents. 3f showed 4-fold higher activity (6.25 mu M) in the biofilms dispersal assay and significantly higher antibacterial activity (MIC 3.125 mu M) in comparison to the 3-(5-((6- (ethoxycarbonyl)-5-(benzo[1,3]dioxol-5-yl)-3-oxo-7-phenyl- thiazolo[3,2-a]pyrimidin-2(5H)-ylidene)methyl) furan-2-yl)benzoic acid (1). (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.12.014

文献信息

• Thiazolidione derivatives as novel antibiofilm agents: Design, synthesis, biological evaluation, and structure–activity relationships
  作者：Bin Pan、Renzheng Huang、Likang Zheng、Chen Chen、Shiqing Han、Di Qu、Mingli Zhu、Ping Wei

  DOI：10.1016/j.ejmech.2010.12.014

  日期：2011.3

  Rational designed novel thiazolidiones were synthesized and evaluated for antibiofilm activity. The active derivatives were not only potent inhibitors of Staphylococcus epidermidis biofilm growth but also efficient antibacterial agents. 3f showed 4-fold higher activity (6.25 mu M) in the biofilms dispersal assay and significantly higher antibacterial activity (MIC 3.125 mu M) in comparison to the 3-(5-((6- (ethoxycarbonyl)-5-(benzo[1,3]dioxol-5-yl)-3-oxo-7-phenyl- thiazolo[3,2-a]pyrimidin-2(5H)-ylidene)methyl) furan-2-yl)benzoic acid (1). (C) 2010 Elsevier Masson SAS. All rights reserved.