Synthesis, antimicrobial activity and quantum chemical investigation of novel succinimide derivatives
Authorized Users Only
2019
Authors
Petković-Cvetković, JelenaBožić, Bojan
Banjac, Nebojša
Petrović, Jovana
Soković, Marina
Vitnik, Vesna
Vitnik, Željko
Ušćumlić, Gordana
Valentić, Nataša
Article (Published version)
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Show full item recordAbstract
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, H-1 NMR, C-13 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:
Succinimide / Antimicrobial activity / Antifungal activity / DFT calculation / Structure-activity relationshipSource:
Journal of Molecular Structure, 2019, 1181, 148-156Publisher:
- Elsevier Science Bv, Amsterdam
Funding / projects:
- Modeling and Numerical Simulations of Complex Many-Body Systems (RS-171017)
- 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
Institution/Community
Tehnološko-metalurški fakultetTY - JOUR AU - Petković-Cvetković, Jelena AU - Božić, Bojan AU - Banjac, Nebojša AU - Petrović, Jovana AU - Soković, Marina AU - Vitnik, Vesna AU - Vitnik, Željko AU - Ušćumlić, Gordana AU - Valentić, Nataša PY - 2019 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4309 AB - 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, H-1 NMR, C-13 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). PB - Elsevier Science Bv, Amsterdam T2 - Journal of Molecular Structure T1 - Synthesis, antimicrobial activity and quantum chemical investigation of novel succinimide derivatives EP - 156 SP - 148 VL - 1181 DO - 10.1016/j.molstruc.2018.12.083 ER -
@article{ author = "Petković-Cvetković, Jelena and Božić, Bojan and Banjac, Nebojša and Petrović, Jovana and Soković, Marina and Vitnik, Vesna and Vitnik, Željko and Ušćumlić, Gordana and Valentić, Nataša", year = "2019", 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, H-1 NMR, C-13 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).", publisher = "Elsevier Science Bv, Amsterdam", journal = "Journal of Molecular Structure", title = "Synthesis, antimicrobial activity and quantum chemical investigation of novel succinimide derivatives", pages = "156-148", volume = "1181", doi = "10.1016/j.molstruc.2018.12.083" }
Petković-Cvetković, J., Božić, B., Banjac, N., Petrović, J., Soković, M., Vitnik, V., Vitnik, Ž., Ušćumlić, G.,& Valentić, N.. (2019). Synthesis, antimicrobial activity and quantum chemical investigation of novel succinimide derivatives. in Journal of Molecular Structure Elsevier Science Bv, Amsterdam., 1181, 148-156. https://doi.org/10.1016/j.molstruc.2018.12.083
Petković-Cvetković J, Božić B, Banjac N, Petrović J, Soković M, Vitnik V, Vitnik Ž, Ušćumlić G, Valentić N. Synthesis, antimicrobial activity and quantum chemical investigation of novel succinimide derivatives. in Journal of Molecular Structure. 2019;1181:148-156. doi:10.1016/j.molstruc.2018.12.083 .
Petković-Cvetković, Jelena, Božić, Bojan, Banjac, Nebojša, Petrović, Jovana, Soković, Marina, Vitnik, Vesna, Vitnik, Željko, Ušćumlić, Gordana, Valentić, Nataša, "Synthesis, antimicrobial activity and quantum chemical investigation of novel succinimide derivatives" in Journal of Molecular Structure, 1181 (2019):148-156, https://doi.org/10.1016/j.molstruc.2018.12.083 . .