2-(4-chlorobenzylthio)-6-(2-methylpropyl)-4-(3-trifluoromethylanilino)pyrimidine-5-carbonitrile | 1427782-58-8

• 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: 2-(4-chlorobenzylthio)-6-(2-methylpropyl)-4-(3-trifluoromethylanilino)pyrimidine-5-carbonitrile
• 英文别名: 2-[(4-chlorobenzyl)sulfanyl]-4-(2-methylpropyl)-6-[(3-trifluoromethyl)anilino]pyrimidine-5-carbonitrile；2-[(4-Chlorophenyl)methylsulfanyl]-4-(2-methylpropyl)-6-[3-(trifluoromethyl)anilino]pyrimidine-5-carbonitrile
• CAS: 1427782-58-8
• 化学式: C₂₃H₂₀ClF₃N₄S
• 分子量: 476.953
• InChiKey: AXKLITSOOFYQPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  86.9
• 氢给体数：
  1
• 氢受体数：
  8

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 乙醇 、 N,N-二甲基乙酰胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.67h， 生成 2-(4-chlorobenzylthio)-6-(2-methylpropyl)-4-(3-trifluoromethylanilino)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, FT-Raman), HOMO–LUMO, NBO analysis and molecular docking study of 2-[(4-chlorobenzyl)sulfanyl]-4-(2-methylpropyl)-6-[3-trifluoromethyl)-anilino]pyrimidine-5-carbonitrile, a potential chemotherapeutic agent
  作者：Fatmah A.M. Al-Omary、Asha Raj、K. Raju、C. Yohannan Panicker、Nadia G. Haress、Ali A. El-Emam、Mahmoud B. El-Ashmawy、Abdulaziz A. Al-Saadi、Christian Van Alsenoy、Javeed Ahmad War

  DOI：10.1016/j.saa.2014.09.066

  日期：2015.2

  FT-IR and FT-Raman spectra of 2-[(4-chlorobenzyl)sulfanyl]-4-(2-methylpropyl)-6-[3-trifluoromethyl)-anilino]pyrimidine-5-carbonitrile were recorded and analyzed. The vibrational wave numbers were computed using DFT quantum chemical calculations. The data obtained from wave number calculations are used to assign vibrational bands obtained in infrared and Raman spectra. Potential energy distribution was done using GAR2PED program. The NH stretching wave number is red shifted by102 cm(-1) in IR from the computed wave number, which indicates the weakening of the NH bond. The geometrical parameters (DFT) of the title compound are in agreement with the XRD results. NBO analysis, HOMO-LUMO, first hyperpolarizability and molecular electrostatic potential results are also reported. From the MEP map it is evident that the negative electrostatic potential regions are mainly localized over the C N and CF3 groups and are possible sites for electrophilic attack and positive regions are localized around NH group, indicating possible sites for nucleophilic attack. The preliminary docking results suggest that the title compound might exhibit inhibitory activity against GPb and may act as a potential anti-diabetic compound. (C) 2014 Elsevier B.V. All rights reserved.