Synthesis, antimicrobial activity and quantum chemical investigation of novel succinimide derivatives
Samo za registrovane korisnike
2019
Autori
Cvetković, J.P.Božić, Bojan
Banjac, Nebojša R.
Petrović, J.
Soković, Marina
Vitnik, Vesna
Vitnik, Željko
Ušćumlić, Gordana
Valentić, Nataša V.
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
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).
Ključne reči:
Antifungal activity / Antimicrobial activity / DFT calculation / Structure-activity relationship / SuccinimideIzvor:
Journal of Molecular Structure, 2019, 1181, 148-156Izdavač:
- Elsevier
Finansiranje / projekti:
- Proučavanje sinteze, strukture i aktivnosti organskih jedinjenja prirodnog i sintetskog porekla (RS-172013)
- Racionalni dizajn i sinteza biološki aktivnih i koordinacionih jedinjenja i funkcionalnih materijala, relevantnih u (bio)nanotehnologiji (RS-172035)
- Bioinformatički metodi za detekciju promotera i teorijsko modelovanje genskih kola (RS-173052)
- Ispitivanje mogućnosti korišćenja kontaminiranih voda za gajenje alternativnih, zdravstveno bezbednih žita (RS-31006)
- Karakterizacija i primena metabolita gljiva i utvrđivanje potencijala novih biofungicida (RS-173032)
DOI: 10.1016/j.molstruc.2018.12.083
ISSN: 0022-2860
WoS: 000458612300016
Scopus: 2-s2.0-85059576086
Institucija/grupa
IHTMTY - JOUR AU - Cvetković, J.P. AU - Božić, Bojan AU - Banjac, Nebojša R. AU - Petrović, J. AU - Soković, Marina AU - Vitnik, Vesna AU - Vitnik, Željko AU - Ušćumlić, Gordana AU - Valentić, Nataša V. PY - 2019 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/2494 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, 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). PB - Elsevier T2 - Journal of Molecular Structure T1 - Synthesis, antimicrobial activity and quantum chemical investigation of novel succinimide derivatives VL - 1181 SP - 148 EP - 156 DO - 10.1016/j.molstruc.2018.12.083 ER -
@article{ author = "Cvetković, J.P. and Božić, Bojan and Banjac, Nebojša R. and Petrović, J. and Soković, Marina and Vitnik, Vesna and Vitnik, Željko and Ušćumlić, Gordana and Valentić, Nataša V.", 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, 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).", publisher = "Elsevier", journal = "Journal of Molecular Structure", title = "Synthesis, antimicrobial activity and quantum chemical investigation of novel succinimide derivatives", volume = "1181", pages = "148-156", doi = "10.1016/j.molstruc.2018.12.083" }
Cvetković, J.P., Božić, B., Banjac, N. R., Petrović, J., Soković, M., Vitnik, V., Vitnik, Ž., Ušćumlić, G.,& Valentić, N. V.. (2019). Synthesis, antimicrobial activity and quantum chemical investigation of novel succinimide derivatives. in Journal of Molecular Structure Elsevier., 1181, 148-156. https://doi.org/10.1016/j.molstruc.2018.12.083
Cvetković J, Božić B, Banjac NR, Petrović J, Soković M, Vitnik V, Vitnik Ž, Ušćumlić G, Valentić NV. 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 .
Cvetković, J.P., Božić, Bojan, Banjac, Nebojša R., Petrović, J., Soković, Marina, Vitnik, Vesna, Vitnik, Željko, Ušćumlić, Gordana, Valentić, Nataša V., "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 . .