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

Handle URI:
http://hdl.handle.net/10754/556925
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
Authors:
Aouad, Mohamed Reda; Messali, Mouslim; Rezki, Nadjet; Ali, Adeeb Al-Sheikh; Lesimple, Alain
Abstract:
(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.
KAUST Department:
Center for Desert Agriculture
Citation:
Synthesis and characterization of some novel 1,2,4-triazoles, 1,3,4-thiadiazoles and Schiff bases incorporating imidazole moiety as potential antimicrobial agents 2015, 65 (2) Acta Pharmaceutica
Journal:
Acta Pharmaceutica
Issue Date:
23-May-2015
DOI:
10.1515/acph-2015-0011
Type:
Article
ISSN:
1846-9558
Additional Links:
http://www.degruyter.com/view/j/acph.2015.65.issue-2/acph-2015-0011/acph-2015-0011.xml
Appears in Collections:
Articles; Center for Desert Agriculture

Full metadata record

DC FieldValue Language
dc.contributor.authorAouad, Mohamed Redaen
dc.contributor.authorMessali, Mouslimen
dc.contributor.authorRezki, Nadjeten
dc.contributor.authorAli, Adeeb Al-Sheikhen
dc.contributor.authorLesimple, Alainen
dc.date.accessioned2015-06-15T13:23:11Zen
dc.date.available2015-06-15T13:23:11Zen
dc.date.issued2015-05-23en
dc.identifier.citationSynthesis and characterization of some novel 1,2,4-triazoles, 1,3,4-thiadiazoles and Schiff bases incorporating imidazole moiety as potential antimicrobial agents 2015, 65 (2) Acta Pharmaceuticaen
dc.identifier.issn1846-9558en
dc.identifier.doi10.1515/acph-2015-0011en
dc.identifier.urihttp://hdl.handle.net/10754/556925en
dc.description.abstract(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.en
dc.relation.urlhttp://www.degruyter.com/view/j/acph.2015.65.issue-2/acph-2015-0011/acph-2015-0011.xmlen
dc.rightsArchived with thanks to Acta Pharmaceutica. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License. (CC BY-NC-ND 3.0) http://creativecommons.org/licenses/by-nc-nd/3.0/en
dc.subjectantimicrobial activityen
dc.subjectSchiff basesen
dc.subject1,3,4-thiadiazoleen
dc.subject1,2,4-triazoleen
dc.subjectimidazoleen
dc.titleSynthesis and characterization of some novel 1,2,4-triazoles, 1,3,4-thiadiazoles and Schiff bases incorporating imidazole moiety as potential antimicrobial agentsen
dc.typeArticleen
dc.contributor.departmentCenter for Desert Agricultureen
dc.identifier.journalActa Pharmaceuticaen
dc.eprint.versionPublisher's Version/PDFen
dc.contributor.institutionDepartment of Chemistry Faculty of Sciences, Taibah University Al-Madinah Al-Munawarah P.O. Box 30002, Saudi Arabiaen
dc.contributor.institutionDepartment 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, Algeriaen
kaust.authorLesimple, Alainen
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