Spectroscopic and quantum chemical elucidation of newly synthesized 1-aryl-3-methyl-3-phenylpyrrolidine-2,5-diones as potential anticonvulsant agents
Authors
Petković Cvetković, JelenaBožić, Bojan

Banjac, Nebojša R.

Lađarević, Jelena

Vitnik, Vesna

Vitnik, Željko

Valentić, Nataša V.

Ušćumlić, Gordana

Article (Published version)
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Show full item recordAbstract
Novel succinimide derivatives were synthesized from 3-methyl-3-phenylsuccinic acid and substituted anilines under solvent-free conditions by using microwave irradiation. All obtained compounds were characterized by ultraviolet (UV), Fourier-transform infrared (FT-IR), 1H and 13С nuclear magnetic resonance (NMR) spectroscopy as well as by elemental analysis. The influence of the substituent electronic effects on spectroscopic data was analyzed by applying the Hammett equation. Moreover, a detailed interpretation and comparison of experimentally obtained and theoretically calculated FT-IR, UV and NMR spectra was performed. Density functional theory (DFT) calculated data of the investigated succinimides were obtained and analyzed in order to determine their structural, spectroscopic and electronic properties. Furthermore, ADMET factor profiling and in-silico prediction of potential biological activities of novel succinimide derivatives have been performed.
Novi derivati sukcinimida sintetisani su polazeći od 3-metil-3-fenilćilibarne kiseline i supstituisanih analina u mikrotalasnom reaktoru u odsustvu rastvarača. Sva jedinjenja su okarakterisana primenom UV-vidljive spektroskopije, infracrvene spektroskopije sa Furijeovom transformacijom (FT-IR), protonske nuklearne magnetne rezonancije (1H NMR), nuklearne magnetne rezonancije ugljenika-13, (13С NMR), kao i elementalnom analizom. Uticaj elektronskih efekata supstituenata na spektroskopske podatke analiziran je upotrebom Hametove jednačine. Takođe, izvršena je detaljna interpretacija, kao i poređenje eksperimentalno dobijenih i teorijski izračunatih FT-IR, UV i NMR spektara. Pored toga, urađeno je ADMET (engl. absorption, distribution, metabolism, excretion and toxicity) profilisanje i in-silico predviđanje potencijalne biološke aktivnosti novosintetisanih derivata sukcinimida.
Keywords:
Sukcinimidi / Elektronski efekat / Kvantno-hemijski proračun / Spektroskopska analiza / Succinimide / electronic effect / spectroscopic analysis / quantum chemical calculationSource:
Hemijska industrija, 2019, 73, 2, 125-137Publisher:
- Belgrade : Association of the Chemical Engineers of Serbia
Funding / projects:
- Investigating the possibility of using contaminated waters for cultivation of pseudocereals (RS-31006)
- 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)
- Modeling and Numerical Simulations of Complex Many-Body Systems (RS-171017)
DOI: 10.2298/HEMIND190214011P
ISSN: 0367-598X; 0350-249X
WoS: 000466161800006
Scopus: 2-s2.0-85069653687
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Institution/Community
IHTMTY - JOUR AU - Petković Cvetković, Jelena AU - Božić, Bojan AU - Banjac, Nebojša R. AU - Lađarević, Jelena AU - Vitnik, Vesna AU - Vitnik, Željko AU - Valentić, Nataša V. AU - Ušćumlić, Gordana PY - 2019 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/3206 AB - Novel succinimide derivatives were synthesized from 3-methyl-3-phenylsuccinic acid and substituted anilines under solvent-free conditions by using microwave irradiation. All obtained compounds were characterized by ultraviolet (UV), Fourier-transform infrared (FT-IR), 1H and 13С nuclear magnetic resonance (NMR) spectroscopy as well as by elemental analysis. The influence of the substituent electronic effects on spectroscopic data was analyzed by applying the Hammett equation. Moreover, a detailed interpretation and comparison of experimentally obtained and theoretically calculated FT-IR, UV and NMR spectra was performed. Density functional theory (DFT) calculated data of the investigated succinimides were obtained and analyzed in order to determine their structural, spectroscopic and electronic properties. Furthermore, ADMET factor profiling and in-silico prediction of potential biological activities of novel succinimide derivatives have been performed. AB - Novi derivati sukcinimida sintetisani su polazeći od 3-metil-3-fenilćilibarne kiseline i supstituisanih analina u mikrotalasnom reaktoru u odsustvu rastvarača. Sva jedinjenja su okarakterisana primenom UV-vidljive spektroskopije, infracrvene spektroskopije sa Furijeovom transformacijom (FT-IR), protonske nuklearne magnetne rezonancije (1H NMR), nuklearne magnetne rezonancije ugljenika-13, (13С NMR), kao i elementalnom analizom. Uticaj elektronskih efekata supstituenata na spektroskopske podatke analiziran je upotrebom Hametove jednačine. Takođe, izvršena je detaljna interpretacija, kao i poređenje eksperimentalno dobijenih i teorijski izračunatih FT-IR, UV i NMR spektara. Pored toga, urađeno je ADMET (engl. absorption, distribution, metabolism, excretion and toxicity) profilisanje i in-silico predviđanje potencijalne biološke aktivnosti novosintetisanih derivata sukcinimida. PB - Belgrade : Association of the Chemical Engineers of Serbia T2 - Hemijska industrija T1 - Spectroscopic and quantum chemical elucidation of newly synthesized 1-aryl-3-methyl-3-phenylpyrrolidine-2,5-diones as potential anticonvulsant agents VL - 73 IS - 2 SP - 125 EP - 137 DO - 10.2298/HEMIND190214011P ER -
@article{ author = "Petković Cvetković, Jelena and Božić, Bojan and Banjac, Nebojša R. and Lađarević, Jelena and Vitnik, Vesna and Vitnik, Željko and Valentić, Nataša V. and Ušćumlić, Gordana", year = "2019", abstract = "Novel succinimide derivatives were synthesized from 3-methyl-3-phenylsuccinic acid and substituted anilines under solvent-free conditions by using microwave irradiation. All obtained compounds were characterized by ultraviolet (UV), Fourier-transform infrared (FT-IR), 1H and 13С nuclear magnetic resonance (NMR) spectroscopy as well as by elemental analysis. The influence of the substituent electronic effects on spectroscopic data was analyzed by applying the Hammett equation. Moreover, a detailed interpretation and comparison of experimentally obtained and theoretically calculated FT-IR, UV and NMR spectra was performed. Density functional theory (DFT) calculated data of the investigated succinimides were obtained and analyzed in order to determine their structural, spectroscopic and electronic properties. Furthermore, ADMET factor profiling and in-silico prediction of potential biological activities of novel succinimide derivatives have been performed., Novi derivati sukcinimida sintetisani su polazeći od 3-metil-3-fenilćilibarne kiseline i supstituisanih analina u mikrotalasnom reaktoru u odsustvu rastvarača. Sva jedinjenja su okarakterisana primenom UV-vidljive spektroskopije, infracrvene spektroskopije sa Furijeovom transformacijom (FT-IR), protonske nuklearne magnetne rezonancije (1H NMR), nuklearne magnetne rezonancije ugljenika-13, (13С NMR), kao i elementalnom analizom. Uticaj elektronskih efekata supstituenata na spektroskopske podatke analiziran je upotrebom Hametove jednačine. Takođe, izvršena je detaljna interpretacija, kao i poređenje eksperimentalno dobijenih i teorijski izračunatih FT-IR, UV i NMR spektara. Pored toga, urađeno je ADMET (engl. absorption, distribution, metabolism, excretion and toxicity) profilisanje i in-silico predviđanje potencijalne biološke aktivnosti novosintetisanih derivata sukcinimida.", publisher = "Belgrade : Association of the Chemical Engineers of Serbia", journal = "Hemijska industrija", title = "Spectroscopic and quantum chemical elucidation of newly synthesized 1-aryl-3-methyl-3-phenylpyrrolidine-2,5-diones as potential anticonvulsant agents", volume = "73", number = "2", pages = "125-137", doi = "10.2298/HEMIND190214011P" }
Petković Cvetković, J., Božić, B., Banjac, N. R., Lađarević, J., Vitnik, V., Vitnik, Ž., Valentić, N. V.,& Ušćumlić, G.. (2019). Spectroscopic and quantum chemical elucidation of newly synthesized 1-aryl-3-methyl-3-phenylpyrrolidine-2,5-diones as potential anticonvulsant agents. in Hemijska industrija Belgrade : Association of the Chemical Engineers of Serbia., 73(2), 125-137. https://doi.org/10.2298/HEMIND190214011P
Petković Cvetković J, Božić B, Banjac NR, Lađarević J, Vitnik V, Vitnik Ž, Valentić NV, Ušćumlić G. Spectroscopic and quantum chemical elucidation of newly synthesized 1-aryl-3-methyl-3-phenylpyrrolidine-2,5-diones as potential anticonvulsant agents. in Hemijska industrija. 2019;73(2):125-137. doi:10.2298/HEMIND190214011P .
Petković Cvetković, Jelena, Božić, Bojan, Banjac, Nebojša R., Lađarević, Jelena, Vitnik, Vesna, Vitnik, Željko, Valentić, Nataša V., Ušćumlić, Gordana, "Spectroscopic and quantum chemical elucidation of newly synthesized 1-aryl-3-methyl-3-phenylpyrrolidine-2,5-diones as potential anticonvulsant agents" in Hemijska industrija, 73, no. 2 (2019):125-137, https://doi.org/10.2298/HEMIND190214011P . .