1-(Biphenyl-4-yl)-2-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]ethanone | 512807-46-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(Biphenyl-4-yl)-2-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]ethanone
• 英文别名: 2-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]-1-(4-phenylphenyl)ethanone
• CAS: 512807-46-4
• 化学式: C₁₇H₁₄N₂OS₂
• 分子量: 326.443
• InChiKey: PZZHHKTYUJFVNW-UHFFFAOYSA-N

物化性质

• 沸点：
  526.4±52.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  96.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(Biphenyl-4-yl)-2-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]ethanone 、 2-氨基二苯甲酮 在 ytterbium(III) chloride 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以82%的产率得到2-((2-((1,1'-biphenyl)-4-yl)-4-phenylquinolin-3-yl)thio)-5-methyl-1,3,4-thiadiazole
  参考文献：
  名称：

  Synthesis of 3-heteroarylthioquinoline derivatives and their in vitro antituberculosis and cytotoxicity studies

  摘要：

  A series of 3-heteroarylthioquinoline derivatives has been synthesized by the Friedlander annulation of 2-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]-1-aryl-1-ethanone/2-(1,3-benzothiazol-2-ylsulfanyl)-1-aryl-1-ethanone/1-aryl-2-[(2-phenyl-2H-1,2,3,4-tetraazol-5-yl)sulfanyl]-1-ethanone with 2-aminobenzophenone in good yields using YbCl3 as the catalyst. These compounds have been screened for their in vitro activity against Mycobacterium tuberculosis H37Rv (MTB) and among the 21 compounds screened, 2-[2-(4-bromophenyl)-4-phenyl-3-quinolyl]sulfanyl-5-methyl-1,3,4-thiadiazole (5d) and 2-[2-(4-chlorophenyl)-4-phenyl-3-quinolyl]sulfanyl-5-methyl-1,3,4-thiadiazole (5c) were found to be the most active compounds with MIC of 3.2 and 3.5 mu M respectively against MTB. The cytotoxic effects against mouse fibroblasts (NIH 3T3) in vitro were evaluated for 5c and 5d, which displayed no toxic effects (IC50 > 1000 mu M) against the mouse fibroblast cell line NIH 3T3. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.046

文献信息

• Synthesis of 3-heteroarylthioquinoline derivatives and their in vitro antituberculosis and cytotoxicity studies
  作者：Selvam Chitra、Nidhin Paul、Shanmugam Muthusubramanian、Paramasivam Manisankar、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.ejmech.2011.07.046

  日期：2011.10

  A series of 3-heteroarylthioquinoline derivatives has been synthesized by the Friedlander annulation of 2-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]-1-aryl-1-ethanone/2-(1,3-benzothiazol-2-ylsulfanyl)-1-aryl-1-ethanone/1-aryl-2-[(2-phenyl-2H-1,2,3,4-tetraazol-5-yl)sulfanyl]-1-ethanone with 2-aminobenzophenone in good yields using YbCl3 as the catalyst. These compounds have been screened for their in vitro activity against Mycobacterium tuberculosis H37Rv (MTB) and among the 21 compounds screened, 2-[2-(4-bromophenyl)-4-phenyl-3-quinolyl]sulfanyl-5-methyl-1,3,4-thiadiazole (5d) and 2-[2-(4-chlorophenyl)-4-phenyl-3-quinolyl]sulfanyl-5-methyl-1,3,4-thiadiazole (5c) were found to be the most active compounds with MIC of 3.2 and 3.5 mu M respectively against MTB. The cytotoxic effects against mouse fibroblasts (NIH 3T3) in vitro were evaluated for 5c and 5d, which displayed no toxic effects (IC50 > 1000 mu M) against the mouse fibroblast cell line NIH 3T3. (C) 2011 Elsevier Masson SAS. All rights reserved.