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Journal of Chinese Pharmaceutical Sciences ›› 2018, Vol. 27 ›› Issue (5): 307-323.DOI: 10.5246/jcps.2018.05.032

• Original articles • Previous Articles     Next Articles

Synthesis, characterization and biological applications of novel Schiff bases of 2-(trifluoromethoxy) aniline

Thierry Youmbi Fonkui1, Monisola Itohan Ikhile2*, Freddy Munyololo Muganza3, Marthe Carine Djuidje Fotsing2, Charmaine Arderne4, Xavier Siwe-Noundou5, Rui Werner Macedo Krause5, Derek Tantoh Ndinteh2*, Patrick Berka Njobeh1   

  1. 1. Department of Biotechnology and Food Technology, P.O. Box 17011, Doornfontein Campus 2028, University of Johannesburg, South Africa
    2. Department of Applied Chemistry, P.O. Box 17011, Doornfontein Campus 2028, University of Johannesburg, South Africa
    3. Department of Chemistry, Sefako Makgatho Health Sciences University, Molotlegi Street, Ga-Rankuwa 0204, Pretoria, South Africa
    4. Department of Chemistry, P. O. Box 524, Auckland Park, Johannesburg, 2006, University of Johannesburg, South Africa
    5. Department of Chemistry, P.O. Box 94, Grahamstown 6140, Rhodes University, South Africa
  • Received:2018-01-13 Revised:2018-03-22 Online:2018-05-31 Published:2018-04-18
  • Contact: Tel.: +2711559 6425, E-mail: miikhile@gmail.com; dndinteh@uj.ac.za

Abstract:

A series of five new Schiff bases (15) were synthesized by reacting 2-(trifluoromethoxy) aniline with different aromatic aldehydes. The Schiff base compounds were characterized by spectroscopic and analytical methods. Crystal structure of one new compound was also reported. The pharmacological properties, including antibacterial (14 bacterial species), antifungal (7 strains),antimalarial, anti-trypanosomal and anti-HIV activities of the compounds, were investigated. Cytotoxicity of the tested compounds was evaluated against human cervix adernocarcinoma cells (HeLa). Bacterial minimum inhibitory concentration (MIC) results by broth microdilution method showed that Bacillus subtilis, Enterococcus faecalis, Staphylococcus aureus, Staphylococcus epidermidis, Proteus vulgaris, Klebsiella oxytoc and Klebsiella pneumonia were more sensitive in the presence of tested compounds with an MIC value of 15.6 µg/mL. All the tested compounds showed good to moderate activity against fungi. The sensitivity of Aspergillus fumigatus was higher than other strains with aminimum cell death concentration (MFC) of 15.6 µg/mL. Compound 1 showed greater antimalarial and anti-trypanosomal properties with very low to no cytotoxic effects against HeLa cells as compared with compound 5, while other compounds exhibited poor activity. Compounds 15 demonstrated good activity against HIV type-1. These Schiff base compounds could be used as good antimicrobial agents. 

Key words: Synthesis, Biological activity, Schiff bases, Antimicrobial, 2-(Trifluoromethoxy) aniline

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