4-(4-fluorophenyl)-6-phenyl-3,4-dihydropyrimidine-2(1H)-thione | 380560-03-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-(4-fluorophenyl)-6-phenyl-3,4-dihydropyrimidine-2(1H)-thione
• 英文别名: 4-(4-fluorophenyl)-6-phenyl-3,4-dihydro-1H-pyrimidine-2-thione
• CAS: 380560-03-2
• 化学式: C₁₆H₁₃FN₂S
• 分子量: 284.357
• InChiKey: PNDQFIRJQKWOHK-UHFFFAOYSA-N

物化性质

• 熔点：
  72 °C(Solv: ethanol (64-17-5))
• 沸点：
  426.9±55.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  56.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(4-fluorophenyl)-6-phenyl-3,4-dihydropyrimidine-2(1H)-thione 在 sodium acetate 、 乙酸酐 、 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Salama; El-Essa, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 1, p. 173 - 179

  摘要：

  DOI：
• 作为产物：
  描述：

  苯乙酮 在 potassium hydroxide 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 4.0h， 生成 4-(4-fluorophenyl)-6-phenyl-3,4-dihydropyrimidine-2(1H)-thione
  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

• Structure Based Library Design (SBLD) for new 1,4-dihydropyrimidine scaffold as simultaneous COX-1/COX-2 and 5-LOX inhibitors
  作者：Deepak Lokwani、Rajaram Azad、Aniket Sarkate、Pallu Reddanna、Devanand Shinde

  DOI：10.1016/j.bmc.2015.06.008

  日期：2015.8

  The various scaffolds containing 1,4-dihydropyrimidine ring were designed by considering the environment of the active site of COX-1/COX-2 and 5-LOX enzymes. The structure-based library design approach, including the focused library design (Virtual Combinatorial Library Design) and virtual screening was used to select the 1,4-dihydropyrimidine scaffold for simultaneous inhibition of both enzyme pathways (COX-1/COX-2 and 5-LOX). The virtual library on each 1,4-dihydropyrimidine scaffold was enumerated in two alternative ways. In first way, the chemical reagents at R groups were filtered by docking of scaffold with single position substitution, that is, only at R-1, or R-2, or R-3, ... R-n on COX-2 enzyme using Glide XP docking mode. The structures that do not dock well were removed and the library was enumerated with filtered chemical reagents. In second alternative way, the single position docking stage was bypassed, and the entire library was enumerated using all chemical reagents by docking on the COX-2 enzyme. The entire library of approximately 15,629 compounds obtained from both ways after screening for drug like properties, were further screened for their binding affinity against COX-1 and 5-LOX enzymes using Virtual Screening Workflow. Finally, 142 hits were obtained and divided into two groups based on their binding affinity for COX-1/COX-2 and for both enzyme pathways (COX-1/COX-2 and 5-LOX). The ten molecules were selected, synthesized and evaluated for their COX-1, COX-2 and 5-LOX inhibiting activity. (C) 2015 Elsevier Ltd. All rights reserved.
• 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.
• Salama; El-Essa, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 1, p. 173 - 179
  作者：Salama、El-Essa

  DOI：——

  日期：——