4-benzylsulfanyl-2-methylsulfanyl-6-oxo-1,6-dihydropyrimidine-5-carbonitrile | 277749-55-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-benzylsulfanyl-2-methylsulfanyl-6-oxo-1,6-dihydropyrimidine-5-carbonitrile
• CAS: 277749-55-0
• 化学式: C₁₃H₁₁N₃OS₂
• 分子量: 289.382
• InChiKey: MMFUSUOJMMQVSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  69.54
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-benzylsulfanyl-2-methylsulfanyl-6-oxo-1,6-dihydropyrimidine-5-carbonitrile 在 三氯氧磷 作用下， 反应 5.0h， 以64.2%的产率得到2-Benzylsulfanyl-4-chloro-6-methylsulfanyl-pyrimidine-5-carbonitrile
  参考文献：
  名称：

  Chloropyrimidines as a new class of antimicrobial agents

  摘要：

  In the course of our investigations of pyrimidines as antimycotic agents, we have identified a sub-class, with significant in vitro activity against mycobacteria. The salient feature of these pyrimidine derivatives (3a-o and 7a,b) is their appended aryl, heteroaryl and alkylthio substituent at position 6 and also alkylthio substituent at position 2. The rational design, synthesis, and evaluation of the in vitro antibacterial activity against six pathogenic bacteria including virulent and non-virulent strains of Mycobacterium tuberculosis is described. Some of the synthesized compounds (3c, 3h, 3i, 3o) have displayed only potent in vitro antimycobacterial activity with MIC of 0.75 mug/mL except 3i which also demonstrated activity against Escherichia coli at 12.5 mug/ mL concentration. Only two compounds, 3a and 3b, demonstrated antibacterial activity against Pseudomonas aeruginosa and E. coli with MIC 12.5 mug/mL. All the synthesized compounds were also evaluated for their antimycotic activity against five pathogenic fungi but only some of them 3j-n and 7a,b were found most potent against Aspergillus fumigatus and Trichophyton mentagrophytes. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00374-1
• 作为产物：
  描述：

  2-氰-3,3-二(甲硫基)丙烯酸甲酯 、 苄基异硫脲 以87.86%的产率得到4-benzylsulfanyl-2-methylsulfanyl-6-oxo-1,6-dihydropyrimidine-5-carbonitrile
  参考文献：
  名称：

  Chloropyrimidines as a new class of antimicrobial agents

  摘要：

  In the course of our investigations of pyrimidines as antimycotic agents, we have identified a sub-class, with significant in vitro activity against mycobacteria. The salient feature of these pyrimidine derivatives (3a-o and 7a,b) is their appended aryl, heteroaryl and alkylthio substituent at position 6 and also alkylthio substituent at position 2. The rational design, synthesis, and evaluation of the in vitro antibacterial activity against six pathogenic bacteria including virulent and non-virulent strains of Mycobacterium tuberculosis is described. Some of the synthesized compounds (3c, 3h, 3i, 3o) have displayed only potent in vitro antimycobacterial activity with MIC of 0.75 mug/mL except 3i which also demonstrated activity against Escherichia coli at 12.5 mug/ mL concentration. Only two compounds, 3a and 3b, demonstrated antibacterial activity against Pseudomonas aeruginosa and E. coli with MIC 12.5 mug/mL. All the synthesized compounds were also evaluated for their antimycotic activity against five pathogenic fungi but only some of them 3j-n and 7a,b were found most potent against Aspergillus fumigatus and Trichophyton mentagrophytes. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00374-1

文献信息

• Suitably functionalised pyrimidines as potential antimycotic agents
  作者：Nidhi Agarwal、Sandeep K. Raghuwanshi、D.N. Upadhyay、P.K. Shukla、Vishnu J. Ram

  DOI：10.1016/s0960-894x(00)00091-3

  日期：2000.4

  Various suitably functionalised pyrimidine derivatives have been synthesized to explore their potential as antimycotic agents. Some of the synthesized compounds 4c, 4d, 8a-e have shown highly significant in vitro antifungal activity against five human pathogenic fungi. (C) 2000 Elsevier Science Ltd. All rights reserved.