N-(4-fluorophenyl)-6-methyl-4-(4-nitrophenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide | 537678-78-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-fluorophenyl)-6-methyl-4-(4-nitrophenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide
• 英文别名: N-(4-fluorophenyl)-6-methyl-4-(4-nitrophenyl)-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxamide
• CAS: 537678-78-7
• 化学式: C₁₈H₁₅FN₄O₃S
• 分子量: 386.407
• InChiKey: DEEHYFFJKSZJAA-UHFFFAOYSA-N

物化性质

• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  131
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(4-fluorophenyl)-6-methyl-4-(4-nitrophenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide 、 邻氯氯苄 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以52%的产率得到4-fluorophenyl 2-(2-chlorobenzylsulfanyl)-4-(4-nitrophenyl)-6-methyl-1,4-dihydro-5-pyrimidinecarboxamide
  参考文献：
  名称：

  Antihypertensive activity of newer 1,4-dihydro-5-pyrimidine carboxamides: Synthesis and pharmacological evaluation

  摘要：

  A number of 5-(4-substituted phenyl)-2-(substiruted benzylsulfanyl)-4-(substituted phenyl)-6-methyl-1,4-dihydro-5-pyrimidine carboxamides (1-30) were designed and synthesized keeping in view the structural requirements as suggested in the pharmacophore model for antihypertensive activity. All the synthesized compounds were tested for antihypertensive activity by non-invasive blood pressure (NIBP) measurements (tail-cuff method) in rats. Almost all the tested compounds displayed considerable decrease in the blood pressure as compared to control. Thirteen compounds showed significant antihypertensive activity comparable to the standard drug nifedipine. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.08.022
• 作为产物：
  描述：

  4-氟苯胺 在 盐酸 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 生成 N-(4-fluorophenyl)-6-methyl-4-(4-nitrophenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of newer thiazolo [3,2-a] pyrimidines for anti-inflammatory and antinociceptive activity

  摘要：

  A new series of thiazolo [3,2-a] pyrimidine derivatives was designed and synthesized using 4-fluoroaniline and ethylacetoacetate as starting material. Anti-inflammatory activity was assessed by the rat paw edema method and antinociceptive activity was evaluated by thermal stimulus technique. The compounds 5-(4-chlorophenyl)-2-(4-fluorobenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidine-6-carboxylic acid (4-fluorophenyl)amide (3l) and 2-(4-chlorobenzylidene)-5-(4-fluorophenyl)-7-methyl-3-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidine-6-carboxylic acid (4-fluorophenyl)amide (3q) were found to possess significant anti-inflammatory and antinociceptive activities. These compounds also showed lower ulcerogenic activity and higher ALD(50) values. Compounds with an aryl ring substituted with a smaller electron withdrawing group at the fourth position displayed better activity than the other derivatives.

  DOI：

  10.1007/s00044-009-9267-8

文献信息

• Catalyst-Free, Rapid Synthesis of Fused Bicyclic Thiazolo-Pyrimidine and Pyrimido-Thiazine Derivatives by a Microwave-Assisted Method
  作者：Vijay R. Virsodia、Nikhil R. Vekariya、Atul T. Manvar、Rupesh C. Khunt、Bhavin R. Marvania、Bharat S. Savalia、Anamik K. Shah

  DOI：10.1080/10426500802077564

  日期：2008.12.23

  The present investigation deals with the rapid microwave-assisted synthesis of compounds containing fused bicyclic systems. Dihydropyrimidines obtained via a microwave-assisted Biginelli reaction were treated with dibromo alkanes under microwave conditions to yield thiazolo-pyrimidine and pyrimido-thiazine systems. The usefulness of this method lies in carrying out the reaction without a catalyst and solvent in a shorter time. The reaction was successfully extended to develop fused systems from benzimidazole-2-thiol.