4-(4-chlorophenyl)-4′-methyl-2′-phenyl-2,5′-bithiazole | 1569318-89-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(4-chlorophenyl)-4′-methyl-2′-phenyl-2,5′-bithiazole
• 英文别名: 4-(4-Chlorophenyl)-4'-methyl-2'-phenyl-2,5'-bithiazole；5-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]-4-methyl-2-phenyl-1,3-thiazole
• CAS: 1569318-89-3
• 化学式: C₁₉H₁₃ClN₂S₂
• 分子量: 368.911
• InChiKey: PPAHKCIJADUWNO-UHFFFAOYSA-N

物化性质

• 熔点：
  158-160 °C
• 沸点：
  571.5±60.0 °C(predicted)
• 密度：
  1.322±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  82.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-甲基-2-苯基-1,3-噻唑-5-甲腈 在 sodium hydrosulfide hydrate 、 magnesium(II) chloride hexahydrate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 4-(4-chlorophenyl)-4′-methyl-2′-phenyl-2,5′-bithiazole
  参考文献：
  名称：

  Synthesis, antimycobacterial screening and molecular docking studies of 4-aryl-4′-methyl-2′-aryl-2,5′-bisthiazole derivatives

  摘要：

  A series of 4-aryl-4'-methyl-2'-aryl-2,5'-bisthiazole derivatives (5a-o) were synthesized and screened for inhibitory activity against Mycobacterium tuberculosis H37Ra (ATCC 25177) and Mycobacterium bovis BCG (ATCC 35743) strains. Five lead compounds (5e, 5f, 5g, 5h, and 5o) were further confirmed from their dose dependent effect against MTB and Bovine-Calmette-Guerin. The most promising compounds 5f (MIC90: 11.32 mu g/mL), 5h (MIC90: 11.59 mu g/mL), and 5o (MIC90: 23.64 mu g/mL) showed strong antitubercular activity against dormant MTB and BCG as well as almost insignificant cytotoxicity up to 100 mu g/mL against HeLa, A549, and PANC-1 human cancer cell lines. Further, the synthesized compounds were found to have potential antibacterial activity against Gram-negative bacteria, Escherichia coli, Pseudomonas flurescence and Gram-positive bacteria, Staphylococcus aureus, Bacillus subtilis. Most of the synthesized compounds showed moderate activity against fungal strain Candida albicans. Molecular docking studies of these compounds showed significant interactions with crystal structure of the cytochrome P45014 alpha-sterol demethylase (CYP51) PDB ID: 1E9X. Hydrogen bond interactions with SER261 and VAL395 are important interactions for selective inhibition of designed inhibitors. Compounds 5f, 5h, and 5o showed significant interactions with 1E9X. All the experimental results promote us to consider this series as a starting point for the development of novel, selective and more potent antitubercular agents in the future.

  DOI：

  10.1007/s00044-017-1988-5