Synthesis and characterization of some novel 1,2,4-triazoles, 1,3,4-thiadiazoles and Schiff bases incorporating imidazole moiety as potential antimicrobial agents

(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...

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Main Authors: Aouad Mohamed Reda, Messali Mouslim, Rezki Nadjet, Ali Adeeb Al-Sheikh, Lesimple Alain
Format: Article
Language:English
Published: Sciendo 2015-06-01
Series:Acta Pharmaceutica
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Online Access:https://doi.org/10.1515/acph-2015-0011
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author Aouad Mohamed Reda
Messali Mouslim
Rezki Nadjet
Ali Adeeb Al-Sheikh
Lesimple Alain
author_facet Aouad Mohamed Reda
Messali Mouslim
Rezki Nadjet
Ali Adeeb Al-Sheikh
Lesimple Alain
author_sort Aouad Mohamed Reda
collection DOAJ
description (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.
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spelling doaj-art-c20d44848057494f84b8b818dbab29d82025-02-02T08:32:25ZengSciendoActa Pharmaceutica1846-95582015-06-0165211713210.1515/acph-2015-0011acph-2015-0011Synthesis and characterization of some novel 1,2,4-triazoles, 1,3,4-thiadiazoles and Schiff bases incorporating imidazole moiety as potential antimicrobial agentsAouad Mohamed Reda0Messali Mouslim1Rezki Nadjet2Ali Adeeb Al-Sheikh3Lesimple Alain4Department of Chemistry Faculty of Sciences, Taibah University Al-Madinah Al-Munawarah P.O. Box 30002, Saudi ArabiaDepartment of Chemistry Faculty of Sciences, Taibah University Al-Madinah Al-Munawarah P.O. Box 30002, Saudi ArabiaDepartment of Chemistry Faculty of Sciences, Taibah University Al-Madinah Al-Munawarah P.O. Box 30002, Saudi Arabia 2 Department of Chemistry, Faculty of Sciences, University of Sciences and Technology Mohamed Boudiaf Laboratoire de Chimie and Electrochimie des Complexes Métalliques (LCECM) USTO-MB, P.O. Box 1505 Oran El M`nouar, AlgeriaDepartment of Chemistry Faculty of Sciences, Taibah University Al-Madinah Al-Munawarah P.O. Box 30002, Saudi ArabiaKing Abdullah University of Science and Technology (KAUST) Saudi Arabia(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.https://doi.org/10.1515/acph-2015-0011imidazole1,2,4-triazole1,3,4-thiadiazoleschiff basesantimicrobial activity
spellingShingle Aouad Mohamed Reda
Messali Mouslim
Rezki Nadjet
Ali Adeeb Al-Sheikh
Lesimple Alain
Synthesis and characterization of some novel 1,2,4-triazoles, 1,3,4-thiadiazoles and Schiff bases incorporating imidazole moiety as potential antimicrobial agents
Acta Pharmaceutica
imidazole
1,2,4-triazole
1,3,4-thiadiazole
schiff bases
antimicrobial activity
title Synthesis and characterization of some novel 1,2,4-triazoles, 1,3,4-thiadiazoles and Schiff bases incorporating imidazole moiety as potential antimicrobial agents
title_full Synthesis and characterization of some novel 1,2,4-triazoles, 1,3,4-thiadiazoles and Schiff bases incorporating imidazole moiety as potential antimicrobial agents
title_fullStr Synthesis and characterization of some novel 1,2,4-triazoles, 1,3,4-thiadiazoles and Schiff bases incorporating imidazole moiety as potential antimicrobial agents
title_full_unstemmed Synthesis and characterization of some novel 1,2,4-triazoles, 1,3,4-thiadiazoles and Schiff bases incorporating imidazole moiety as potential antimicrobial agents
title_short Synthesis and characterization of some novel 1,2,4-triazoles, 1,3,4-thiadiazoles and Schiff bases incorporating imidazole moiety as potential antimicrobial agents
title_sort synthesis and characterization of some novel 1 2 4 triazoles 1 3 4 thiadiazoles and schiff bases incorporating imidazole moiety as potential antimicrobial agents
topic imidazole
1,2,4-triazole
1,3,4-thiadiazole
schiff bases
antimicrobial activity
url https://doi.org/10.1515/acph-2015-0011
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