(E)-1-(2,8-bis(trifluoromethyl)quinolin-4-yl)-2-((2,3-dihydrobenzofuran-5-yl)methylene)hydrazine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (E)-1-(2,8-bis(trifluoromethyl)quinolin-4-yl)-2-((2,3-dihydrobenzofuran-5-yl)methylene)hydrazine
• 英文别名: N-[(E)-2,3-dihydro-1-benzofuran-5-ylmethylideneamino]-2,8-bis(trifluoromethyl)quinolin-4-amine
• 化学式: C₂₀H₁₃F₆N₃O
• 分子量: 425.333
• InChiKey: ZHKSCCHMHRDIQM-YPXUMCKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2,3-二氢苯并呋喃-5-甲醛 、 4-hydrazinyl-2,8-bis(trifluoromethyl)quinoline 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 以73%的产率得到(E)-1-(2,8-bis(trifluoromethyl)quinolin-4-yl)-2-((2,3-dihydrobenzofuran-5-yl)methylene)hydrazine
  参考文献：
  名称：

  New quinoline derivatives: Synthesis and investigation of antibacterial and antituberculosis properties

  摘要：

  Four new series of quinoline derivatives were synthesized starting from 2-trifluoromethyl aniline through multi-step reactions. In the reaction sequence, substituted aniline was cyclized to 4-hydroxy quinoline 1, which was then transformed to 4-chloro-2,8-bis(trifluoromethyl)quinoline 2. The key scaffold 4-hydrazinyl-2,8-bis(trifluoromethyl)quinoline 3, obtained from the compound 2, was successfully converted to target quinoline derivatives, viz. hydrazones 4a-t, ureas 5a-e, thioureas 6a-c and pyrazoles 7a-d, in good yields. The newly synthesized title compounds were evaluated for their in vitro antibacterial activity against Escherichia coli. Staphylococcus aureus, Pseudomonas aeruginosa and Klebsiella pneumoniae (recultured) and antituberculosis activity against Mycobacterium tuberculosis H(37)Rv and MDR-TB. Preliminary results indicated that most of the hydrazone derivatives demonstrated very good antibacterial and antituberculosis activities while other derivatives showed moderate activity. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.04.022

文献信息

• New quinoline derivatives: Synthesis and investigation of antibacterial and antituberculosis properties
  作者：Sumesh Eswaran、Airody Vasudeva Adhikari、Imran H. Chowdhury、Nishith K. Pal、K.D. Thomas

  DOI：10.1016/j.ejmech.2010.04.022

  日期：2010.8

  Four new series of quinoline derivatives were synthesized starting from 2-trifluoromethyl aniline through multi-step reactions. In the reaction sequence, substituted aniline was cyclized to 4-hydroxy quinoline 1, which was then transformed to 4-chloro-2,8-bis(trifluoromethyl)quinoline 2. The key scaffold 4-hydrazinyl-2,8-bis(trifluoromethyl)quinoline 3, obtained from the compound 2, was successfully converted to target quinoline derivatives, viz. hydrazones 4a-t, ureas 5a-e, thioureas 6a-c and pyrazoles 7a-d, in good yields. The newly synthesized title compounds were evaluated for their in vitro antibacterial activity against Escherichia coli. Staphylococcus aureus, Pseudomonas aeruginosa and Klebsiella pneumoniae (recultured) and antituberculosis activity against Mycobacterium tuberculosis H(37)Rv and MDR-TB. Preliminary results indicated that most of the hydrazone derivatives demonstrated very good antibacterial and antituberculosis activities while other derivatives showed moderate activity. (C) 2010 Elsevier Masson SAS. All rights reserved.