The new Schiff bases of 2-alkylthio-5-(4-aminophenyl)-1,3,4-oxadiazoles and their antimicrobial activity

• Published in: Journal of the Iranian Chemical Society Vol. 16; no. 3; pp. 545 - 551
• Main Authors: Ismailova, D. S., Ziyaev, A. A., Bobakulov, Kh. M., Sasmakov, S. A., Makhmudov, U. S., Yusupova, E. G., Azimova, Sh. S.
• Format: Journal Article
• Language: English
• Published: Berlin/Heidelberg Springer Berlin Heidelberg 13.03.2019; Springer Nature B.V
• Subjects: Aldehydes; Analytical Chemistry; Aromatic compounds; Bacteria; Biochemistry; Chemistry; Chemistry and Materials Science; E coli; Fungicides; Gram-positive bacteria; Halides; Imines; Inorganic Chemistry; NMR; Nuclear magnetic resonance; Organic Chemistry; Original Paper; Oxadiazoles; Physical Chemistry; Synthesis; Antimicrobial activity; X-ray analysis; NMR spectra; Aromatic aldehyde; Amino group; 5-(4-Aminophenyl)-1,3,4-oxadiazol-2-thione
• ISSN: 1735-207X; 1735-2428
• DOI: 10.1007/s13738-018-1530-9

By the reaction of 5-(4-aminophenyl)-1,3,4-oxadiazolin-2-thione with alkyl halides 2-alkylthio-5-(4-aminophenyl)-1,3,4-oxadiazoles, 2–4 were obtained. By the reaction of compounds 2–4 with aromatic aldehydes, new Schiff bases 5a – d and 6a – d were synthesized. The structures of synthesized compounds are confirmed by the IR, UV, 1 H NMR for all compounds, 13 C NMR for compounds 3, 4, 5a–5d, 6a, 6d and X-ray for compound 3 . All substances were tested in vitro for their antibacterial and antifungal activity. The results showed that Compound 2 exhibited remarkable activity against Candida albicans . Compounds 5а – d were found to exhibit a weak selective activity against Gram-positive bacteria of Bacillus subtilis and compounds 6а – d against Gram-negative bacteria of Escherichia coli .