期刊
ACTA PHARMACEUTICA
卷 65, 期 2, 页码 117-132出版社
HRVATSKO FARMACEUTSKO DRUSTOV (HFD)-CROATION PHARMACEUTICAL SOC
DOI: 10.1515/acph-2015-0011
关键词
imidazole; 1,2,4-triazole; 1,3,4-thiadiazole; Schiff bases; antimicrobial activity
(1,4,5-Triphenylimidazol-2-yl-thio) butyric acid hydrazide (3) was obtained via alkylation of 1,4,5-triphenylimidazol-2-thiol (1) with ethylbromobutyrate, followed by addition of hydrazine hydrate. Treatment of acid hydrazide 3 with carbon disulfide in an ethanolic potassium hydroxide solution gave the intermediate potassium dithiocarbazinate salt, which was cyclized to 4-amino-5-[(1,4,5-triphenylimidazol-2-yl)thiopropyl]-2H-1,2,4-triazole-3-thione (4) in the presence of hydrazine hydrate. Condensation of compound 3 with alkyl/arylisothiocyanate afforded the corresponding 1-[4-(1,4,5-triphenylimidazol-2-ylthio)butanoyl]-4-alkyl/arylthiosemicarbazides (5-7),which upon refluxing with sodium hydroxide, yielded the corresponding 1,2,4-triazole-3-thiols 8-10. Under acidic conditions, compounds 4-6 were converted to aminothiadiazoles 11-13. Moreover, the series of Schiff bases 14-18 were synthesized from the condensation of compound 3 with different aromatic aldehydes. The newly synthesized compounds were characterized by IR, H-1 NMR, C-13 NMR and mass spectral analyses. They were also preliminarily screened for their antimicrobial activity.
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