Synthesis of Some New 6-Methylimid azo [2,1-b] thiazole-5-carbohydrazide Derivatives and their Antimicrobial Activities

Summary

In this study, 14 new compounds having 6-methyl-N²-(alkylidene/cycloalkylidene) imidazo [2,1-b] thiazole-5-carbohydrazide (3a-g), 3-[[(6-methylimid-azo [2,1-b] thiazole- 5 -yl)carbonyl] amino]-4-thiazolidinone (4a-d) and 4-[[(6methyl-imidazo [2,1-b] thiazole-5-yl) carbonyl] amino]-1-thia-4-azaspiro[4.4]nonan/[4.5]dec-an-3-one (4e-g) structures were synthesized. The structures of the compounds were elucidated by UV, IR, ¹H-NMR, ¹³C-NMR, ¹H-¹³C-COSY, mass spectra and elemental analysis. All compounds synthesized were tested for antimicrobial activity against Staphylococcus aureus ATCC 6538, Staphylococcus epidermidis ATCC 12228, Escherichia coli ATCC 8739, Klebsiella pneumoniae ATCC 4352, Pseudomonas aeruginosa ATCC 1539, Salmonella thypi, Shigella flexneri, Proteus mirabilis ATCC 14153, Candida albicans ATCC 10231 and Mycobacterium tuberculosis H₃₇Rv. Only 4d and 4f demonstrated antimicrobial activity against S. epidermidis ATCC 12228 (MIC: 19.5 µg/ml and 39 µg/ml, respectively).

Zusammenfassung

Synthese neuer 6-Methylimidazo[2,1-b]thiazol-5-carbohydrazid-Derivate und Bewertung ihrer mikrobiologischen Wirkung

In dieser Arbeit wurden 14 neue Verbindungen mit den Grundstrukturen 6-Methyl-N₂-(alkyliden/cycloalkyliden)imidazo [2,1-b] thiazol-5-carbohydrazid (3a-g), 3-[[(6-Methylimidazo [2,1-b]thiazol-5-yl)carbonyl]amino]4-thiazolidinon (4a-d) und 4-[[(6-Methylimidazo[2,1-b]thiazol-5-yl) carbonyl] amino]-1-thia-4-azaspiro [4.4]nonan/[4.5]decan-3-on (4e-g) dargestellt. Alle Strukturen wurden mittels UV, IR, ¹H-NMR, ¹³C-NMR, ¹H-¹³C-COSY, Massenspektroskopie und Elementaranalyse aufgeklärt. Alle Verbindungen wurden gegen Staphylococcus aureus ATCC 6538, Staphylococcus epidermidis ATCC 12228, Escherichia coli ATCC 8739, Klebsiella pneumoniae ATCC 4352, Pseudomonas aeruginosa ATCC 1539, Salmonella thypi, Shigella flexneri, Proteus mirabilis ATCC 14153, Candida albicans ATCC 10231 und Mycobacterium tuberculosis H₃₇Rv mikrobiologisch getestet. Nur 4d und 4f erwiesen sich gegen S. epidermidis ATCC 12228 als aktiv (MIC: 19.5 µg/ml und 39 Hg/ml).

Key words

Hydrazide-hydrazones - Imidazo[2,1-b]thiazoles, antimicrobial activity, synthesis - 1-Thia-4-azaspiro[4.4]nonan-3-one, antimicrobial activity, synthesis - 1-Thia-4-azaspiro[4.5]decan-3-ones, antimicrobial activity, synthesis - 4-Thiazolidinones, antimicrobial activity, synthesis