Synthesis and antibacterial activity of 3-substituted 1-(2-methyl-5-nitrophenyl)-5-oxopyrrolidine derivatives

A series of new 1,3-disubstituted pyrrolidinone derivatives bearing triazole, thiazole, thiadiazole, oxadiazole, sulfamoylphenyl, etc., moieties were synthesized from 1-(2-methyl-5-nitrophenyl)-5-oxopyrrolidine-3-carbohydrazide. Reactions of 5-substituted 4-amino-1,2,4-triazole with α-haloketones we...

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Bibliographic Details
Published in:Research on chemical intermediates 2019-11, Vol.45 (11), p.5499-5517
Main Authors: Balandis, Benas, Anusevičius, Kazimieras, Šiugždaitė, Jūratė, Kantminienė, Kristina, Mickevičius, Vytautas
Format: Article
Language:English
Subjects:
Catalysis
Chemistry
Chemistry and Materials Science
Derivatives
E coli
Inorganic Chemistry
Pathogens
Physical Chemistry
Substitutes
Triazoles
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Summary:A series of new 1,3-disubstituted pyrrolidinone derivatives bearing triazole, thiazole, thiadiazole, oxadiazole, sulfamoylphenyl, etc., moieties were synthesized from 1-(2-methyl-5-nitrophenyl)-5-oxopyrrolidine-3-carbohydrazide. Reactions of 5-substituted 4-amino-1,2,4-triazole with α-haloketones were investigated leading to the target [1, 2, 4]triazolo[3,4- b ][1, 3, 4]thiadiazine derivatives. The synthesized compounds were tested for antibacterial activity against S. aureus , L. monocytogenes , E. coli , and P. aeruginosa . The 1-(2-Methyl-5-nitrophenyl)-5-oxo- N -(3-sulfamoylphenyl)pyrrolidine-3-carboxamide and its 4-sulfamoylphenyl analogue have demonstrated excellent antibacterial activity with MIC and MBC values of 7.8 and 15.6 µg/mL, respectively, against P. aeruginosa and L. monocytogenes .
ISSN:0922-6168
1568-5675
DOI:10.1007/s11164-019-03916-y