Synthesis and antibacterial activity of some new thiazole and thiophene derivatives.
Dibenzobarrelene 1 was reacted with cyanoacetic acid hydrazide and thiosemicarbazide to give the corresponding 3-oxo-propiononitrile and thioamide derivatives 2 and 16, respectively. The base-catalyzed reaction 3-oxo-propiononitrile derivative 2 with phenyl isothiocyanate yielded the non-isolable intermediate 3. Treatment of 3 with dilute HCl afforded the corresponding thiocarbamoyl derivative 4. The intermediate 3, thiocarbamoyl 4 and thioamide derivatives 16 were utilized as key intermediates for the synthesis of some new thiazole 5, 6a, 6b, 7, 8, 10a, 10b, 12, 14a, 15, 17a, 17b, and 18; and thiophene 13a-d derivatives, respectively. The newly synthesized compounds were characterized by IR, (1)H NMR, (13)C NMR and mass spectral studies. Representative compounds of the synthesized product were tested and evaluated as antibacterial agent.
Khalil
A M
AM
Chemistry Department, Faculty of Science, Mansoura University, Mansoura, Egypt.
Berghot
M A
MA
Gouda
M A
MA
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001407:Bacillus / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D013844:Thiazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013876:Thiophenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
D000900:Anti-Bacterial Agents; D013844:Thiazoles; D013876:Thiophenes