Synthesis of novel seco-acyclo-N-diazolyl-thione nucleosides analogous derived from acetic acid: characterization, complex formation with ions Pb(II), Hg(II) and antibacterial activity

• Published in: Journal of the Iranian Chemical Society 2022-03, Vol.19 (3), p.893-899
• Main Authors: Chehrouri, Manel, Othman, Adil A.
• Format: Article
• Language: English
• Subjects: Acetic acid; Analytical Chemistry; Bacteria; Biochemistry; Chemical synthesis; Chemistry; Chemistry and Materials Science; Complex formation; Ethyl acetate; Gram-positive bacteria; Infrared spectroscopy; Inorganic Chemistry; Lead; Mercury (metal); Mercury compounds; NMR spectroscopy; Nucleosides; Organic Chemistry; Original Paper; Oxadiazoles; Physical Chemistry; Physical properties; Spectrum analysis; Thiadiazoles; Vancomycin
• ISSN: 1735-207X; 1735-2428
• DOI: 10.1007/s13738-021-02358-x

Three diazoles namely 5-methyl-1,3,4-oxadiazole -2(3H)-thione, 5-methyl-1,3,4-thiadiazol-2(3H)-thione and 4-amino-5-methyl-2H-1,2,4-triazole-3-thiol were synthesized from acetic acid or ethyl acetate. Seco-acyclo-N-nucleoside analogous was synthesized by condensation of 1,3-benzylidine-glyceryl-2-tosylate with the three diazoles. Structural proof was based upon IR, 1 H-NMR, 13 C-NMR spectroscopy and MS measurements. The tendency to form complex between 1,3,4-oxadiazole and 1,3,4-thiadiazoles and Pb(II) and Hg(II) ions was achieved, and their structures were assigned by observing some changes in physical properties such as, MP, coloration, R f (TLC), IR and UV spectroscopy. Most compounds were tested in vitro against Gram-positive and Gram-negative bacteria and showed variable activity. Hg 2+  complexes of oxadiazole and thiadiazole derivatives exhibited appreciable antibacterial effect at lower MIC, compatible to the reference vancomycin. Similarly, oxadiazole-nucleoside exhibited high effect on Gram-positive bacteria. Graphic abstract