5-(4-methoxyphenyl)-7-phenyl-2H-thiazolo[3,2-a]pyrimidin-3(5H)-one | 511309-24-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(4-methoxyphenyl)-7-phenyl-2H-thiazolo[3,2-a]pyrimidin-3(5H)-one
• 英文别名: 5-(4-methoxyphenyl)-7-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-3(2H)-one；5-(4-methoxyphenyl)-7-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-3-one
• CAS: 511309-24-3
• 化学式: C₁₉H₁₆N₂O₂S
• 分子量: 336.414
• InChiKey: VFOJJRDTBCSNBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  67.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(5-甲酰基-2-呋喃基)苯甲酸 、 5-(4-methoxyphenyl)-7-phenyl-2H-thiazolo[3,2-a]pyrimidin-3(5H)-one 在 溶剂黄146 、 β-丙氨酸 作用下， 反应 1.0h， 生成 3-(5-((5-(4-methoxyphenyl)-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：

  4-甲氧基查耳酮 在 sodium acetate 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 9.0h， 生成 5-(4-methoxyphenyl)-7-phenyl-2H-thiazolo[3,2-a]pyrimidin-3(5H)-one
  参考文献：
  名称：

  Synthesis, antimicrobial and DFT studies of novel fused thiazolopyrimidine derivatives

  摘要：

  通过将chalcone 3与硫脲缩合得到的dihydropyrimidine-2(1H)-thione 4与氯乙酸和1,2-二溴乙烷反应，生成了化合物5和6，而不是它们的异构体8和9。通过元素分析、1H NMR、13C NMR、IR和质谱数据，确定了环化产物的区域化学性质及其结构。使用密度泛函理论(DFT)计算了化合物5a及其异构体8a，使用B3LYP密度泛函方法和6-31G**基组，Jaguar版本6.5112进行了计算。计算了化合物5a及其可能的异构体8a的1H和13C NMR谱，并与实验结果进行了相关性分析。通过两种途径获得了5的2-芳基衍生物，并通过光谱数据确定了它们的结构。对化合物4-7进行了抗菌活性筛选。

  DOI：

  10.1515/hc-2013-0024

文献信息

• Synthesis, antimicrobial and DFT studies of novel fused thiazolopyrimidine derivatives
  作者：Richa Gupta、Ram Pal Chaudhary

  DOI：10.1515/hc-2013-0024

  日期：2013.6.1

  The reaction of dihydropyrimidine-2(1H)-thione 4, obtained by the condensation of chalcone 3 with thiourea, with chloroacetic acid and 1,2-dibromoethane furnished compounds 5 and 6 and not their respective isomers 8 and 9. The regiochemistry of the cyclized products and their structure was established by elemental analysis, ¹H NMR, ¹³C NMR, IR and mass spectral data. Density functional theory (DFT) calculations have been carried out for compound 5a and its isomer 8a with Jaguar version 6.5112 using B3LYP density functional method and 6–31G** basis set. ¹H and ¹³C NMR spectra of compound 5a and its possible isomer 8a have been calculated and correlated with experimental results. 2-Arylidene derivatives of 5 were obtained by two routes and their structure was established by spectral data. Compounds 4–7 were screened for their antimicrobial activities.

  通过将chalcone 3与硫脲缩合得到的dihydropyrimidine-2(1H)-thione 4与氯乙酸和1,2-二溴乙烷反应，生成了化合物5和6，而不是它们的异构体8和9。通过元素分析、1H NMR、13C NMR、IR和质谱数据，确定了环化产物的区域化学性质及其结构。使用密度泛函理论(DFT)计算了化合物5a及其异构体8a，使用B3LYP密度泛函方法和6-31G**基组，Jaguar版本6.5112进行了计算。计算了化合物5a及其可能的异构体8a的1H和13C NMR谱，并与实验结果进行了相关性分析。通过两种途径获得了5的2-芳基衍生物，并通过光谱数据确定了它们的结构。对化合物4-7进行了抗菌活性筛选。
• Biological evaluation of halogenated thiazolo[3,2-a]pyrimidin-3-one carboxylic acid derivatives targeting the YycG histidine kinase
  作者：Dan Zhao、Chen Chen、Huayong Liu、Likang Zheng、Yao Tong、Di Qu、Shiqing Han

  DOI：10.1016/j.ejmech.2014.09.096

  日期：2014.11

  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.