Acta Pharmaceutica, Vol. 65 No. 2, 2015.
Izvorni znanstveni članak
https://doi.org/10.1515/acph-2015-0011
Synthesis and characterization of some novel 1,2,4-triazoles, 1,3,4-thiadiazoles and Schiff's bases incorporating imidazole moiety as potential antimicrobial agents
MOHAMED REDA AOUAD
; Department of Chemistry, Faculty of Sciences, Taibah University, Al-Madinah Al-Munawarah, P.O.Box 30002, Saudi Arabia
MOUSLIM MESSALI
; Department of Chemistry, Faculty of Sciences, Taibah University, Al-Madinah Al-Munawarah, P.O.Box 30002, Saudi Arabia; Department of Chemistry, Faculty of Sciences, University of Sciences and Technology Mohamed Boudiaf, Laboratoire de Chimie & Electrochim
NADJET REZKI
; Department of Chemistry, Faculty of Sciences, Taibah University, Al-Madinah Al-Munawarah, P.O.Box 30002, Saudi Arabia
ADEEB AL-SHEIKH ALI
; King Abdullah University of Science and Technology (KAUST), Saudi Arabia
ALAIN LESIMPLE
Sažetak
(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, 1H NMR, 13C NMR and mass spectral analyses. They were also preliminarily screened for their antimicrobial activity.
Ključne riječi
imidazole; 1,2,4-triazole; 1,3,4-thiadiazole; Schiff bases; antimicrobial activity
Hrčak ID:
128990
URI
Datum izdavanja:
30.6.2015.
Posjeta: 1.332 *