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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2015-06-01
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| 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 |
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| 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. |
| format | Article |
| id | doaj-art-c20d44848057494f84b8b818dbab29d8 |
| institution | Kabale University |
| issn | 1846-9558 |
| language | English |
| publishDate | 2015-06-01 |
| publisher | Sciendo |
| record_format | Article |
| series | Acta Pharmaceutica |
| 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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