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Synthesis, antimicrobial activity and quantum chemical investigation of novel succinimide derivatives

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2019
Authors
Cvetković, J.P.
Božić, Bojan
Banjac, Nebojša R.
Petrović, J.
Soković, Marina
Vitnik, Vesna
Vitnik, Željko
Ušćumlić, Gordana
Valentić, Nataša V.
Article (Published version)
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Abstract
In the present study, twelve new 1-aryl-3-ethyl-3-methylpyrrolidine-2,5-diones were synthesized and their structures were characterized by FT-IR, 1H NMR, 13C NMR spectroscopy and elemental analysis. In the final step of synthetic rout, condensation between corresponding succinic acid and substituted anilines has been improved using the microwave irradiation. Significantly higher yields compared to conventional condensation have been observed. The preliminary biological results indicated that some of the synthesized compounds showed promising in vitro antifungal activities towards several test fungi. 1-(4-Bromophenyl)-3-ethyl-3-methylpyrrolidine-2,5-dione (8) exhibited significant in vitro inhibitory activities against broad spectra of fungus, and on the basis of obtained data, the investigated bromo derivative has to be observed as novel potential fungicide. The density functional theory (DFT) calculations have been performed in order to study the structure-activity relationship (SAR) ...of the investigated molecules. In order to prediction of the chemical activity of the molecule, the molecular electrostatic potential (MEP) map was analyzed for the optimized geometry of 1-phenyl-3-ethyl-3-methylpyrrolidine-2,5-dione (4) and 1-(4-bromophenyl)-3-ethyl-3-methylpyrrolidine-2,5-dione (8).

Keywords:
Antifungal activity / Antimicrobial activity / DFT calculation / Structure-activity relationship / Succinimide
Source:
Journal of Molecular Structure, 2019, 1181, 148-156
Publisher:
  • Elsevier B.V.
Projects:
  • Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds (RS-172013)
  • Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-172035)
  • Bioinformatic promoter predictions and theoretical modeling of gene circuits in bacteria (RS-173052)
  • Investigating the possibility of using contaminated waters for cultivation of pseudocereals (RS-31006)
  • Characterization and application of fungal metabolites and assessment of new biofungicides potential (RS-173032)

DOI: 10.1016/j.molstruc.2018.12.083

ISSN: 0022-2860

WoS: 000458612300016

Scopus: 2-s2.0-85059576086
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URI
http://cer.ihtm.bg.ac.rs/handle/123456789/2494
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