Synthesis of novel 1,2,3-thiadizoles and 1,2,3-selenadiazoles as new antimicrobial agents


KUCUK H. B., SALT Z. B., Kara E., MEHAN A. S., Yusufoglu A. S.

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, vol.194, no.9, pp.903-908, 2019 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 194 Issue: 9
  • Publication Date: 2019
  • Doi Number: 10.1080/10426507.2019.1576676
  • Journal Name: PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.903-908
  • Keywords: 1, 2, 3-Thiadiazole, 1, 2, 3-selenadiazole, antibacterial activity, antifungal activity, DERIVATIVES, ELICITORS
  • Istanbul University Affiliated: Yes

Abstract

A series of novel 1,2,3-thiadiazoles and 1,2,3-selenadiazoles having a long alkyl chain were synthesized by reacting semicarbazones with SOCl2 and SeO2, respectively. The structures of the target compounds 5-12 were confirmed by spectroscopy (IR, H-1 NMR, C-13 NMR, and MS) and elemental analysis. Their antibacterial and antifungal activities were evaluated against six bacteria (Pseudomonas aeruginosa, Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, Enterococcus faecalis, Staphylococcus epidermidis, Staphylococcus aureus) and three fungi (Candida albicans, Candida parapsilosis, Candida tropicalis). The results of bioassays indicated that the compounds 5-Dodecyl-4-(4-methoxy-phenyl)-[1-3]selenadiazole (7), 4-Methyl-5-tetradecyl-[1-3]selenadiazole (8) and 5-Dodecyl-4-(4-methoxy-phenyl)-[1-3]thiadiazole (11) displayed moderate antibacterial activity against S. Epidermidis. On the other hand, according to antifungal screening results, compounds 5-Dodecyl-4-phenyl-[1-3]selenadiazole (5), 4-p-Tolyl-5-undecyl-[1-3]selenadiazole (6), and 5-Dodecyl-4-(4-methoxy-phenyl)-[1-3]selenadiazole (7) exhibited significant antifungal activities studied yeast strains.