Spectroscopic and quantum chemical elucidation of newly synthesized 1-aryl-3-methyl-3-phenylpyrrolidine-2,5-diones as potential anticonvulsant agents
Аутори
Petković Cvetković, JelenaBožić, Bojan
Banjac, Nebojša R.
Lađarević, Jelena
Vitnik, Vesna
Vitnik, Željko
Valentić, Nataša V.
Ušćumlić, Gordana
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
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.
Кључне речи:
Sukcinimidi / Elektronski efekat / Kvantno-hemijski proračun / Spektroskopska analiza / Succinimide / electronic effect / spectroscopic analysis / quantum chemical calculationИзвор:
Hemijska industrija, 2019, 73, 2, 125-137Издавач:
- Belgrade : Association of the Chemical Engineers of Serbia
Финансирање / пројекти:
- Испитивање могућности коришћења контаминираних вода за гајење алтернативних, здравствено безбедних жита (RS-MESTD-Technological Development (TD or TR)-31006)
- Проучавање синтезе, структуре и активности органских једињења природног и синтетског порекла (RS-MESTD-Basic Research (BR or ON)-172013)
- Рационални дизајн и синтеза биолошки активних и координационих једињења и функционалних материјала, релевантних у (био)нанотехнологији (RS-MESTD-Basic Research (BR or ON)-172035)
- Биоинформатички методи за детекцију промотера и теоријско моделовање генских кола (RS-MESTD-Basic Research (BR or ON)-173052)
- Моделирање и нумеричке симулације сложених вишечестичних система (RS-MESTD-Basic Research (BR or ON)-171017)
DOI: 10.2298/HEMIND190214011P
ISSN: 0367-598X; 0350-249X
WoS: 000466161800006
Scopus: 2-s2.0-85069653687
Институција/група
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 . .