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Research on Chemical Intermediates

, Volume 45, Issue 11, pp 5499–5517 | Cite as

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

  • Benas Balandis
  • Kazimieras Anusevičius
  • Jūratė Šiugždaitė
  • Kristina Kantminienė
  • Vytautas MickevičiusEmail author
Article
  • 138 Downloads

Abstract

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.

Keywords

Pyrrolidin-2-ones Thiazole Triazole [1,2,4]triazolo[3,4-b][1,3,4]thiadiazine Antibacterial activity 

Notes

Supplementary material

11164_2019_3916_MOESM1_ESM.docx (2.1 mb)
Supplementary material 1 (DOCX 2191 kb)

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Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  • Benas Balandis
    • 1
  • Kazimieras Anusevičius
    • 1
  • Jūratė Šiugždaitė
    • 3
  • Kristina Kantminienė
    • 2
  • Vytautas Mickevičius
    • 1
    Email author
  1. 1.Department of Organic ChemistryKaunas University of TechnologyKaunasLithuania
  2. 2.Department of Physical and Inorganic ChemistryKaunas University of TechnologyKaunasLithuania
  3. 3.Department of Veterinary Pathobiology, Veterinary AcademyLithuanian University of Health SciencesKaunasLithuania

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