CORRELATION OF STRUCTURE AND POTENTIAL PHARMACOLOGICAL ACTIVITY OF SPIROHIDANTOINS DERIVED FROM α-TETRALONE
KORELACIJA STRUKTURE I POTENCIJALNE FARMAKOLOŠKE AKTIVNOSTI SPIROHIDANTOINA DOBIJENIH IZ α-TETRALONA
Authors
Lazić, AnitaĐorđević, Ivana
Gak Simić, Kristina
Matović, Luka
Mašulović, Aleksandra
Lađarević, Jelena
Trišović, Nemanja
Conference object (Published version)
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Hydantoin is a nonaromatic five-membered heterocycle, which is considered a valuable, privileged
scaffold in medicinal chemistry. The importance of the hydantoin scaffold in drug discovery
has been reinforced by several medicines in clinical use, such as anticonvulsants (phenytoin), antibiotics(nitrofurantoin), anticancer drugs (enzalutamide) and keratolytics (allantoin). To design new
potentially pharmacologically active compounds, six spirohydantoin derivatives were synthetized and fully characterized by determination of the melting points, elemental analysis, FT-IR, 1H and 13C NMR spectroscopic methods. Effects of the substituents on the shift of the absorption maxima of synthetized compounds were analyzed using the linear solvatation energy relationship, while the influence of the chemical structure on the pharmacokinetically relevant properties of the investigated spirohydantoin derivatives was evaluated using the Lipinski’s rule of five, Veber, Egan and Ghose’s empirical crite...ria, as well as different in silico methods. In order of detailed analysis of the potential pharmacological activity of the synthesized spirohydantoins, their potential pharmacological properties were correlated with the corresponding solvent effects.
Hidantoin je nearomatičan petočlani ciklični ureid koji predstavlja važan strukturni fragment
velikog broja farmakološki aktivnih jedinjenja. Derivati ovog petočlanog cikličnog ureida primenjuju
se kao antikonvulzivi (fenitoin), antibiotici (nitrofurantoin), antikancerogeni lekovi (enzalutamid) i
keratolitici (alantoin). U cilju dizajniranja novih potencijalno farmakološki aktivnih jedinjenja, u
ovom radu, sintetisano je šest derivata spirohidantoina koji su u potpunosti strukturno okarakterisani
određivanjem temperature topljenja, elementarnom analizom, FT-IR, 1H i 13C NMR spektroskopskim
metodama. Efekat supstituenata na pomeranje maksimuma apsorpcije analiziran je primenom linearne korelacije energije solvatacije, dok je uticaj hemijske strukture na farmakološka svojstva derivata spirohidantoina procenjen primenom “pravila broja pet”, Veberovog, Eganovog i Gozovog
kriterijuma, kao i primenom različitih in silico metoda. U cilju opsežnije analize potencijalne farmakološke akti...vnosti sintetisanih spirohidantoina, korelisana su njihova potencijalna farmakološka
svojstva sa odgovarajućim efektima rastvarača.
Keywords:
imidazolidine-2,4-dione derivatives / Kamlet-Taft equation / lipophilicity / derivati imidazolidin-2,4-diona / Kamlet-Taftova jednačina / lipofilnostSource:
Zbornik radova pisanih za 37. Međunarodni kongres o procesnoj industriji, PROCESING '24, 29–31. maj 2024, Beograd = Proceedings, 2024, 279-288Publisher:
- Beograd : Savez mašinskih i elektrotehničkih inženjera i tehničara Srbije (SMEITS), Društvo za procesnu tehniku
Funding / projects:
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200287 (Innovation Center of the Faculty of Technology and Metallurgy) (RS-MESTD-inst-2020-200287)
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200135 (University of Belgrade, Faculty of Technology and Metallurgy) (RS-MESTD-inst-2020-200135)
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200026 (University of Belgrade, Institute of Chemistry, Technology and Metallurgy - IChTM) (RS-MESTD-inst-2020-200026)
Collections
Institution/Community
Inovacioni centarTY - CONF AU - Lazić, Anita AU - Đorđević, Ivana AU - Gak Simić, Kristina AU - Matović, Luka AU - Mašulović, Aleksandra AU - Lađarević, Jelena AU - Trišović, Nemanja PY - 2024 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/7547 AB - Hydantoin is a nonaromatic five-membered heterocycle, which is considered a valuable, privileged scaffold in medicinal chemistry. The importance of the hydantoin scaffold in drug discovery has been reinforced by several medicines in clinical use, such as anticonvulsants (phenytoin), antibiotics(nitrofurantoin), anticancer drugs (enzalutamide) and keratolytics (allantoin). To design new potentially pharmacologically active compounds, six spirohydantoin derivatives were synthetized and fully characterized by determination of the melting points, elemental analysis, FT-IR, 1H and 13C NMR spectroscopic methods. Effects of the substituents on the shift of the absorption maxima of synthetized compounds were analyzed using the linear solvatation energy relationship, while the influence of the chemical structure on the pharmacokinetically relevant properties of the investigated spirohydantoin derivatives was evaluated using the Lipinski’s rule of five, Veber, Egan and Ghose’s empirical criteria, as well as different in silico methods. In order of detailed analysis of the potential pharmacological activity of the synthesized spirohydantoins, their potential pharmacological properties were correlated with the corresponding solvent effects. AB - Hidantoin je nearomatičan petočlani ciklični ureid koji predstavlja važan strukturni fragment velikog broja farmakološki aktivnih jedinjenja. Derivati ovog petočlanog cikličnog ureida primenjuju se kao antikonvulzivi (fenitoin), antibiotici (nitrofurantoin), antikancerogeni lekovi (enzalutamid) i keratolitici (alantoin). U cilju dizajniranja novih potencijalno farmakološki aktivnih jedinjenja, u ovom radu, sintetisano je šest derivata spirohidantoina koji su u potpunosti strukturno okarakterisani određivanjem temperature topljenja, elementarnom analizom, FT-IR, 1H i 13C NMR spektroskopskim metodama. Efekat supstituenata na pomeranje maksimuma apsorpcije analiziran je primenom linearne korelacije energije solvatacije, dok je uticaj hemijske strukture na farmakološka svojstva derivata spirohidantoina procenjen primenom “pravila broja pet”, Veberovog, Eganovog i Gozovog kriterijuma, kao i primenom različitih in silico metoda. U cilju opsežnije analize potencijalne farmakološke aktivnosti sintetisanih spirohidantoina, korelisana su njihova potencijalna farmakološka svojstva sa odgovarajućim efektima rastvarača. PB - Beograd : Savez mašinskih i elektrotehničkih inženjera i tehničara Srbije (SMEITS), Društvo za procesnu tehniku C3 - Zbornik radova pisanih za 37. Međunarodni kongres o procesnoj industriji, PROCESING '24, 29–31. maj 2024, Beograd = Proceedings T1 - CORRELATION OF STRUCTURE AND POTENTIAL PHARMACOLOGICAL ACTIVITY OF SPIROHIDANTOINS DERIVED FROM α-TETRALONE T1 - KORELACIJA STRUKTURE I POTENCIJALNE FARMAKOLOŠKE AKTIVNOSTI SPIROHIDANTOINA DOBIJENIH IZ α-TETRALONA EP - 288 SP - 279 DO - 10.24094/ptk.024.279 ER -
@conference{ author = "Lazić, Anita and Đorđević, Ivana and Gak Simić, Kristina and Matović, Luka and Mašulović, Aleksandra and Lađarević, Jelena and Trišović, Nemanja", year = "2024", abstract = "Hydantoin is a nonaromatic five-membered heterocycle, which is considered a valuable, privileged scaffold in medicinal chemistry. The importance of the hydantoin scaffold in drug discovery has been reinforced by several medicines in clinical use, such as anticonvulsants (phenytoin), antibiotics(nitrofurantoin), anticancer drugs (enzalutamide) and keratolytics (allantoin). To design new potentially pharmacologically active compounds, six spirohydantoin derivatives were synthetized and fully characterized by determination of the melting points, elemental analysis, FT-IR, 1H and 13C NMR spectroscopic methods. Effects of the substituents on the shift of the absorption maxima of synthetized compounds were analyzed using the linear solvatation energy relationship, while the influence of the chemical structure on the pharmacokinetically relevant properties of the investigated spirohydantoin derivatives was evaluated using the Lipinski’s rule of five, Veber, Egan and Ghose’s empirical criteria, as well as different in silico methods. In order of detailed analysis of the potential pharmacological activity of the synthesized spirohydantoins, their potential pharmacological properties were correlated with the corresponding solvent effects., Hidantoin je nearomatičan petočlani ciklični ureid koji predstavlja važan strukturni fragment velikog broja farmakološki aktivnih jedinjenja. Derivati ovog petočlanog cikličnog ureida primenjuju se kao antikonvulzivi (fenitoin), antibiotici (nitrofurantoin), antikancerogeni lekovi (enzalutamid) i keratolitici (alantoin). U cilju dizajniranja novih potencijalno farmakološki aktivnih jedinjenja, u ovom radu, sintetisano je šest derivata spirohidantoina koji su u potpunosti strukturno okarakterisani određivanjem temperature topljenja, elementarnom analizom, FT-IR, 1H i 13C NMR spektroskopskim metodama. Efekat supstituenata na pomeranje maksimuma apsorpcije analiziran je primenom linearne korelacije energije solvatacije, dok je uticaj hemijske strukture na farmakološka svojstva derivata spirohidantoina procenjen primenom “pravila broja pet”, Veberovog, Eganovog i Gozovog kriterijuma, kao i primenom različitih in silico metoda. U cilju opsežnije analize potencijalne farmakološke aktivnosti sintetisanih spirohidantoina, korelisana su njihova potencijalna farmakološka svojstva sa odgovarajućim efektima rastvarača.", publisher = "Beograd : Savez mašinskih i elektrotehničkih inženjera i tehničara Srbije (SMEITS), Društvo za procesnu tehniku", journal = "Zbornik radova pisanih za 37. Međunarodni kongres o procesnoj industriji, PROCESING '24, 29–31. maj 2024, Beograd = Proceedings", title = "CORRELATION OF STRUCTURE AND POTENTIAL PHARMACOLOGICAL ACTIVITY OF SPIROHIDANTOINS DERIVED FROM α-TETRALONE, KORELACIJA STRUKTURE I POTENCIJALNE FARMAKOLOŠKE AKTIVNOSTI SPIROHIDANTOINA DOBIJENIH IZ α-TETRALONA", pages = "288-279", doi = "10.24094/ptk.024.279" }
Lazić, A., Đorđević, I., Gak Simić, K., Matović, L., Mašulović, A., Lađarević, J.,& Trišović, N.. (2024). CORRELATION OF STRUCTURE AND POTENTIAL PHARMACOLOGICAL ACTIVITY OF SPIROHIDANTOINS DERIVED FROM α-TETRALONE. in Zbornik radova pisanih za 37. Međunarodni kongres o procesnoj industriji, PROCESING '24, 29–31. maj 2024, Beograd = Proceedings Beograd : Savez mašinskih i elektrotehničkih inženjera i tehničara Srbije (SMEITS), Društvo za procesnu tehniku., 279-288. https://doi.org/10.24094/ptk.024.279
Lazić A, Đorđević I, Gak Simić K, Matović L, Mašulović A, Lađarević J, Trišović N. CORRELATION OF STRUCTURE AND POTENTIAL PHARMACOLOGICAL ACTIVITY OF SPIROHIDANTOINS DERIVED FROM α-TETRALONE. in Zbornik radova pisanih za 37. Međunarodni kongres o procesnoj industriji, PROCESING '24, 29–31. maj 2024, Beograd = Proceedings. 2024;:279-288. doi:10.24094/ptk.024.279 .
Lazić, Anita, Đorđević, Ivana, Gak Simić, Kristina, Matović, Luka, Mašulović, Aleksandra, Lađarević, Jelena, Trišović, Nemanja, "CORRELATION OF STRUCTURE AND POTENTIAL PHARMACOLOGICAL ACTIVITY OF SPIROHIDANTOINS DERIVED FROM α-TETRALONE" in Zbornik radova pisanih za 37. Međunarodni kongres o procesnoj industriji, PROCESING '24, 29–31. maj 2024, Beograd = Proceedings (2024):279-288, https://doi.org/10.24094/ptk.024.279 . .