A new class of dihaloquinolones bearing N'-aldehydoglycosylhydrazides, mercapto-1,2,4-triazole, oxadiazoline and a-amino ester precursors: synthesis and antimicrobial activity
Título del documento: A new class of dihaloquinolones bearing N'-aldehydoglycosylhydrazides, mercapto-1,2,4-triazole, oxadiazoline and a-amino ester precursors: synthesis and antimicrobial activity
Revue: Journal of the Brazilian Chemical Society
Base de datos: PERIÓDICA
Número de sistema: 000311288
ISSN: 0103-5053
Autores: 1
2
Instituciones: 1University of Al al-Bayt, College of Science, Al-Mafraq. Jordania
2Universitat Konstanz, Fachbereich Chemie, Konstanz, Baden-Wurttemburg. Alemania
Año:
Periodo: Sep
Volumen: 14
Número: 5
Paginación: 790-796
País: Brasil
Idioma: Inglés
Tipo de documento: Artículo
Enfoque: Experimental, aplicado
Resumen en inglés Reaction of the quinolones 6-8 with hydrazine afforded the hydrazide 9-11 in moderate yields. Condensation of 9 and 11 with CS2 /KOH furnished the potassium salts 13 and 14, respectively, which spontaneously afforded the 3-(1,2,4-triazolyl)-quinolones 15 and 16, respectively, on treatment with hydrazine. Reaction of 9 in refluxing CS2 /KOH gave the 3-(1,2,4-oxadiazolyl)-quinolone 17. Alternatively, 15 was prepared from 17. The azide derivative 12, obtained from 10, furnished the a-amino ester derivative 18, on reaction with the glycine ethyl ester. Coupling of 10 with various sugars gave the N'-aldehydoglycosyl-quinolone-3-yl)carbohydrazides 19a-e. The newly synthesized compounds were screened for their antibacterial activity
Resumen en portugués A reação das quinolonas 6-8 com hidrazina forneceu as hidrazidas 9-11 em rendimentos moderados. A condensação de 9 e 11 com CS2/KOH rendeu os sais de potássio 13 e 14, respectivamente, que espontaneamente forneceram as 3-(1,2,4-triazolil)-quinolonas 15 e 16, respectivamente, quando tratadas com hidrazina. A reação de 9 com CS2/KOH sob refluxo resultou na 3-(1,2,4-oxadiazolil)-quinolona 17. Alternativamente, 15 foi preparado a partir de 17. O derivado 12, obtido a partir de 10, forneceu o derivado a-amino ester 18 mediante reação com o éster etílico da glicina. O acoplamento de 10 com vários açúcares forneceu as N'-(aldeidoglicosil-quinolona-3-il)carbohidrazidas 19a-e. Os novos compostos sintetizados foram avaliados quanto a sua atividade antibacteriana
Disciplinas: Química
Palabras clave: Química farmacéutica,
Actividad antimicrobiana,
Hidrazidas,
Quinolonas
Keyword: Chemistry,
Medicinal chemistry,
Antimicrobial activity,
Hydrazides,
Quinolones
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