2-(4-chlorobenzylthio)-6-(2-methylpropyl)-4-(phenylthio)pyrimidine-5-carbonitrile | 1402215-06-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(4-chlorobenzylthio)-6-(2-methylpropyl)-4-(phenylthio)pyrimidine-5-carbonitrile
• 英文别名: 2-[(4-chlorobenzyl)sulfanyl]-4-(2-methylpropyl)-6-(phenylsulfanyl)pyrimidine-5-carbonitrile；2-[(4-chlorophenyl)methylsulfanyl]-4-(2-methylpropyl)-6-phenylsulfanylpyrimidine-5-carbonitrile
• CAS: 1402215-06-8
• 化学式: C₂₂H₂₀ClN₃S₂
• 分子量: 426.006
• InChiKey: NAMCYPNSQNRWJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-(2-methylpropyl)-4-oxo-2-sulfanylidene-1,2,3,4-tetrahydropyrimidine-5-carbonitrile 在 potassium carbonate 、 三氯氧磷 作用下， 以 吡啶 、 N,N-二甲基乙酰胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.67h， 生成 2-(4-chlorobenzylthio)-6-(2-methylpropyl)-4-(phenylthio)pyrimidine-5-carbonitrile
  参考文献：
  名称：

  Pyrimidine-5-carbonitriles – part III: synthesis and antimicrobial activity of novel 6-(2-substituted propyl)-2,4-disubstituted pyrimidine-5-carbonitriles

  摘要：

  摘要：6-(2-甲基丙基或2-苯基丙基)-2-硫代尿嘧啶-5-碳腈（4a,b）与各种芳基甲基卤化物、2-溴乙基甲醚、苄氯甲基醚和2-溴甲基-5-硝基呋喃在N,N-二甲基甲酰胺或丙酮中反应，产生相应的取代硫代-3,4-二氢-4-氧基嘧啶-5-碳腈类似物5a-h，6a，b，7和8a，b。将5c与氯化磷酸和N,N-二甲基苯胺处理，得到4-氯嘧啶衍生物9，然后与各种芳基硫醇、芳基胺和1-取代哌嗪反应，得到相应的4-芳基硫10a-d，4-芳基胺11a-d和4-哌嗪12a,b衍生物。新合成的化合物被用于对一系列革兰氏阳性和阴性细菌以及类似酵母病原真菌白色念珠菌的体外活性进行测试。化合物5e，5f，5g，h，7，8a，b和12a表现出明显的抗菌活性，特别是对革兰氏阳性细菌。这些化合物中没有一个对白色念珠菌具有活性。

  DOI：

  10.1515/hc-2013-0139

文献信息

• Spectroscopic investigation (FT-IR and FT-Raman), vibrational assignments, HOMO–LUMO, NBO, MEP analysis and molecular docking study of 2-[(4-chlorobenzyl)sulfanyl]-4-(2-methylpropyl)-6-(phenylsulfanyl)-pyrimidine-5-carbonitrile, a potential chemotherapeutic agent
  作者：Nourah Z. Alzoman、Y. Sheena Mary、C. Yohannan Panicker、Ibrahim A. Al-Swaidan、Ali A. El-Emam、Omar A. Al-Deeb、Abdulaziz A. Al-Saadi、Christian Van Alsenoy、Javeed Ahmad War

  DOI：10.1016/j.saa.2014.12.043

  日期：2015.3

  Vibrational spectral analysis of 2-[(4-chlorobenzyl)sulfanyli-4-(2-methylpropy1)-6-(phenylsulfanyl)-pyrimidine-5-carbonitrile was carried out using FT-IR and FT-Raman spectroscopic techniques. The equilibrium geometry and vibrational wave numbers have been computed using density functional B3LYP method with 6-311++G(d,p)(5D,7F) as basis set. Stability of the molecule arising from hyper conjugative interactions, charge delocalization has been analyzed using NBO analysis. The nonlinear optical behavior of the title compound is also theoretically predicted. From the MEP, it is evident that the negative charge covers the C equivalent to N group and the positive region is over the phenyl and the pyrimidine rings. From the potential energy scan it is clear that the lone pairs of the sulfur atom prefer to point away from the pyrimidine ring and the C equivalent to N group resulting with two possible minimum conformations at the N4C8S1C25 angle equal nearly 0 degrees or 150 degrees. Molecular docking results suggest that the compound might exhibit inhibitory activity against GPb and may act as potential anti-diabetic compound. (C) 2014 Elsevier B.V. All rights reserved.