Synthesis, characterization and antimicrobial activity of new 1,2,3-selenadiazoles.
The commercially available aromatic polyketones 1a-d were utilized for the synthesis of the multi-arm1,2,3-selenadiazole derivatives 3a-d. The preparation starts with the reaction between compounds 1a-d and p-toluenesulfonyl hydrazide to give the corresponding tosylhydrazones 2a-d. Subsequent reaction with selenium dioxide leads to regiospecific ring closure of the tosylhydrazones to give the target multi-arm 1,2,3-selenadiazole derivatives in high yield. A 1,2,3-selenadiazole derivative 3e containing an epoxide ring was also prepared. The structures of all the synthesized compounds were confirmed on the basis of spectral and analytical data. The compounds were screened in vitro for their antimicrobial activity against various pathogenic bacterial and Candida strains obtained from King Abdullah Hospital in Irbid -Jordan. Compounds 3a, 3c and 3e were found to be highly active against all the selected pathogens. Compound 3e showed an inhibition zone of 13 mm against the highly resistant P. aruginosa.
Al-Smadi
Mousa
M
Department of Applied Chemical Sciences, Jordan University of Science and Technology, P.O.Box 3030, Irbid 22110, Jordan. mariam10@just.edu.jo
Al-Momani
Fouad
F
D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001393:Azoles / Q000737:chemistry*; D006835:Hydrazones / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D012643:Selenium / Q000737:chemistry*; D013329:Structure-Activity Relationship
D000890:Anti-Infective Agents; D001393:Azoles; D006835:Hydrazones; D007659:Ketones; D016566:Organoselenium Compounds; D012643:Selenium