Sinteza, karakterizacija i ispitivanje antioksidativne aktivnosti estarskih i amidnih derivata 2,6-dimetil-4-supstituisane-1,4-dihidropiridin-3,5-dikarboksilne kiseline
Synthesis, characterization and antioxidative assay of ester and amide derivates of 2,6-dimethyl-4-(substituted)-1,4dihydropyridine-3,5-dicarboxylic acid
Апстракт
U ovom radu je izvršena sinteza šest estarskih derivata 2,6 dimetil4-supstituisane-1,4-dihidropiridin-3,5-dikarboksilne kiseline: dietil2,6-dimetil-4-fenil-1,4-dihidropiridin-3,5 dikarboksilata, dietil-2,6dimetil-4-(3'-nitrofenil)-1,4 dihidropiridin-3,5-dikarboksilata, dietil2,6-dimetil-4-(4' nitrofenil)-1,4-dihidropiridin-3,5-dikarboksilata, dietil-4-(2'-hidroksifenil)-2,6-dimetil-1,4-dihidropiridin-3,5dikarboksilata, dietil-4-(3'-hidroksifenil)-2,6-dimetil-1,4dihidropiridin-3,5-dikarboksilata i dietil-4-(4'-hidroksifenil)-2,6dimetil-1,4-dihidropiridin-3,5-dikarboksilata. Dobijena jedinjenja su zatim korišćena kao polazna za sintezu sledećih amida: 2,6-dimetil-4-N3,N5-di(tiazol-2-il)-1,4dihidropiridin-3,5-dikarboksiamida, 2,6-dimetil-4-(3'-nitrofenil)-N3,N5-di(tiazol-2-il)-1,4-dihidropiridin-3,5-dikarboksiamida, 2,6dimetil-4-(4'-nitrofenil)-N3,N5-di(tiazol-2-il)-1,4-dihidropiridin-3,5dikarboksiamida, 4-(2'-hidroksifenil)-2,6-dimetil-N3,N5-di(tiazol-2il)-1,4-dihidropiridin-3,5-dikarbok...siamida, 4-(3'-hidroksifenil)-2,6dimetil-N3,N5-di(tiazol-2-il)-1,4-dihidropiridin-3,5-dikarboksiamida i 4-(4'-hidroksifenil)-2,6-dimetil-N3,N5-di(tiazol-2-il)-1,4dihidropiridin-3,5-dikarboksiamida. Amidni derivati 2,6-dimetil-4supstituisane-1,4-dihidropiridin-3,5-dikarboksilne kiseline su sintetisani u cilju utvrđivanja uticaja tipa i položaja supstituenta u molekulu na antioksidativnu aktivnost. Iz ove serije, najnižu vrednost IC50, tj. najbolju antioksidativnu aktivnost je pokazao 4(2'-hidroksifenil)-2,6-dimetil-N3,N5-di(tiazol-2-il)-1,4dihidropiridin-3,5-dikarboksiamid, dok su zanemarljive vrednosti pokazali 2,6-dimetil-4-N3,N5-di(tiazol-2-il)-1,4-dihidropiridin-3,5dikarboksiamid i 2,6-dimetil-4-(3'-nitrofenil)-N3,N5-di(tiazol-2-il)-1,4-dihidropiridin-3,5-dikarboksiamid. Ispitivanje antioksidativne aktivnosti je izvršeno merenjem sposobnosti jedinjenja da hvataju slobodne radikale primenom metode inhibicije pomoću DPPH (1,1difenil-2-pikril-hidrazil) radikala. Sintetisana jedinjenja su okarakterisana temperaturom topljenja, elementalnom analizom i FT-IR spektroskopijom.
Six ester and amide derivates of 2,6-dimethyl-4-(substituted)-1,4-dihydropyridine-3,5-dicarboxylic acid have been synthesized in this paper, including: diethyl 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5dicarboxylate, diethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, diethyl 2,6dimethyl-4-(4-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, diethyl 4-(2-hydroxyphenyl)-2,6dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, diethyl 4-(3-hydroxyphenyl)-2,6-dimethyl-1,4dihydropyridine-3,5-dicarboxylate and diethyl 4-(4-hydroxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5dicarboxylate. Obtained ester derivates were used afterwards as a starting compounds for synthesis of amide derivates, including: 2,6-dimethyl-4-phenyl-N3,N5-di(thiazol-2-yl)-1,4-dihydropyridine-3,5-dicarboxamide, 2,6dimethyl-4-(3-nitrophenyl)-N3,N5-di(thiazol-2-yl)-1,4-dihydropyridine-3,5-dicarboxamide, 2,6-dimethyl-4(4-nitrophenyl)-N3,N5-di(thiazol-2-yl)-1,4-dihydropyridine-3,5-dicarboxamide, 4-...(2-hydroxyphenyl)-2,6dimethyl-N3,N5-di(thiazol-2-yl)-1,4-dihydropyridine-3,5-dicarboxamide, 4-(3-hydroxyphenyl)-2,6-dimethylN3,N5-di(thiazol-2-yl)-1,4-dihydropyridine-3,5-dicarboxamide and 4-(4-hydroxyphenyl)-2,6-dimethylN3,N5-di(thiazol-2-yl)-1,4-dihydropyridine-3,5-dicarboxamide. Obtained compounds were characterized by melting point, elementary analysis and FT-IR spectroscopy. In order to determine the effect of the substituent, the antioxidative activity assay of obtained 1,4dihydropyridines was performed by using the DPPH (1,1-diphenyl-2-picryl-hydrazyl) free radical scavenging method.
Кључне речи:
slobodni radikali / estri / DPPH / antioksidativna aktivnost / amidi / 1,4-dihidropiridini / free radicals / esters / DPPH / antioxidative activity / amides / 1,4-dihydropyridinesИзвор:
Journal of Engineering and Processing Management, 2018, 10, 2, 8-15Издавач:
- University of East Sarajevo, Faculty of Technology
Институција/група
Inovacioni centarTY - JOUR AU - Mijatović, Tamara AU - Perić, Milica AU - Matović, Luka AU - Ristović, Marija AU - Drmanić, Saša PY - 2018 UR - https://machinery.mas.bg.ac.rs/handle/123456789/2753 AB - U ovom radu je izvršena sinteza šest estarskih derivata 2,6 dimetil4-supstituisane-1,4-dihidropiridin-3,5-dikarboksilne kiseline: dietil2,6-dimetil-4-fenil-1,4-dihidropiridin-3,5 dikarboksilata, dietil-2,6dimetil-4-(3'-nitrofenil)-1,4 dihidropiridin-3,5-dikarboksilata, dietil2,6-dimetil-4-(4' nitrofenil)-1,4-dihidropiridin-3,5-dikarboksilata, dietil-4-(2'-hidroksifenil)-2,6-dimetil-1,4-dihidropiridin-3,5dikarboksilata, dietil-4-(3'-hidroksifenil)-2,6-dimetil-1,4dihidropiridin-3,5-dikarboksilata i dietil-4-(4'-hidroksifenil)-2,6dimetil-1,4-dihidropiridin-3,5-dikarboksilata. Dobijena jedinjenja su zatim korišćena kao polazna za sintezu sledećih amida: 2,6-dimetil-4-N3,N5-di(tiazol-2-il)-1,4dihidropiridin-3,5-dikarboksiamida, 2,6-dimetil-4-(3'-nitrofenil)-N3,N5-di(tiazol-2-il)-1,4-dihidropiridin-3,5-dikarboksiamida, 2,6dimetil-4-(4'-nitrofenil)-N3,N5-di(tiazol-2-il)-1,4-dihidropiridin-3,5dikarboksiamida, 4-(2'-hidroksifenil)-2,6-dimetil-N3,N5-di(tiazol-2il)-1,4-dihidropiridin-3,5-dikarboksiamida, 4-(3'-hidroksifenil)-2,6dimetil-N3,N5-di(tiazol-2-il)-1,4-dihidropiridin-3,5-dikarboksiamida i 4-(4'-hidroksifenil)-2,6-dimetil-N3,N5-di(tiazol-2-il)-1,4dihidropiridin-3,5-dikarboksiamida. Amidni derivati 2,6-dimetil-4supstituisane-1,4-dihidropiridin-3,5-dikarboksilne kiseline su sintetisani u cilju utvrđivanja uticaja tipa i položaja supstituenta u molekulu na antioksidativnu aktivnost. Iz ove serije, najnižu vrednost IC50, tj. najbolju antioksidativnu aktivnost je pokazao 4(2'-hidroksifenil)-2,6-dimetil-N3,N5-di(tiazol-2-il)-1,4dihidropiridin-3,5-dikarboksiamid, dok su zanemarljive vrednosti pokazali 2,6-dimetil-4-N3,N5-di(tiazol-2-il)-1,4-dihidropiridin-3,5dikarboksiamid i 2,6-dimetil-4-(3'-nitrofenil)-N3,N5-di(tiazol-2-il)-1,4-dihidropiridin-3,5-dikarboksiamid. Ispitivanje antioksidativne aktivnosti je izvršeno merenjem sposobnosti jedinjenja da hvataju slobodne radikale primenom metode inhibicije pomoću DPPH (1,1difenil-2-pikril-hidrazil) radikala. Sintetisana jedinjenja su okarakterisana temperaturom topljenja, elementalnom analizom i FT-IR spektroskopijom. AB - Six ester and amide derivates of 2,6-dimethyl-4-(substituted)-1,4-dihydropyridine-3,5-dicarboxylic acid have been synthesized in this paper, including: diethyl 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5dicarboxylate, diethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, diethyl 2,6dimethyl-4-(4-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, diethyl 4-(2-hydroxyphenyl)-2,6dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, diethyl 4-(3-hydroxyphenyl)-2,6-dimethyl-1,4dihydropyridine-3,5-dicarboxylate and diethyl 4-(4-hydroxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5dicarboxylate. Obtained ester derivates were used afterwards as a starting compounds for synthesis of amide derivates, including: 2,6-dimethyl-4-phenyl-N3,N5-di(thiazol-2-yl)-1,4-dihydropyridine-3,5-dicarboxamide, 2,6dimethyl-4-(3-nitrophenyl)-N3,N5-di(thiazol-2-yl)-1,4-dihydropyridine-3,5-dicarboxamide, 2,6-dimethyl-4(4-nitrophenyl)-N3,N5-di(thiazol-2-yl)-1,4-dihydropyridine-3,5-dicarboxamide, 4-(2-hydroxyphenyl)-2,6dimethyl-N3,N5-di(thiazol-2-yl)-1,4-dihydropyridine-3,5-dicarboxamide, 4-(3-hydroxyphenyl)-2,6-dimethylN3,N5-di(thiazol-2-yl)-1,4-dihydropyridine-3,5-dicarboxamide and 4-(4-hydroxyphenyl)-2,6-dimethylN3,N5-di(thiazol-2-yl)-1,4-dihydropyridine-3,5-dicarboxamide. Obtained compounds were characterized by melting point, elementary analysis and FT-IR spectroscopy. In order to determine the effect of the substituent, the antioxidative activity assay of obtained 1,4dihydropyridines was performed by using the DPPH (1,1-diphenyl-2-picryl-hydrazyl) free radical scavenging method. PB - University of East Sarajevo, Faculty of Technology T2 - Journal of Engineering and Processing Management T1 - Sinteza, karakterizacija i ispitivanje antioksidativne aktivnosti estarskih i amidnih derivata 2,6-dimetil-4-supstituisane-1,4-dihidropiridin-3,5-dikarboksilne kiseline T1 - Synthesis, characterization and antioxidative assay of ester and amide derivates of 2,6-dimethyl-4-(substituted)-1,4dihydropyridine-3,5-dicarboxylic acid EP - 15 IS - 2 SP - 8 VL - 10 DO - 10.7251/JEPM181002008M ER -
@article{ author = "Mijatović, Tamara and Perić, Milica and Matović, Luka and Ristović, Marija and Drmanić, Saša", year = "2018", abstract = "U ovom radu je izvršena sinteza šest estarskih derivata 2,6 dimetil4-supstituisane-1,4-dihidropiridin-3,5-dikarboksilne kiseline: dietil2,6-dimetil-4-fenil-1,4-dihidropiridin-3,5 dikarboksilata, dietil-2,6dimetil-4-(3'-nitrofenil)-1,4 dihidropiridin-3,5-dikarboksilata, dietil2,6-dimetil-4-(4' nitrofenil)-1,4-dihidropiridin-3,5-dikarboksilata, dietil-4-(2'-hidroksifenil)-2,6-dimetil-1,4-dihidropiridin-3,5dikarboksilata, dietil-4-(3'-hidroksifenil)-2,6-dimetil-1,4dihidropiridin-3,5-dikarboksilata i dietil-4-(4'-hidroksifenil)-2,6dimetil-1,4-dihidropiridin-3,5-dikarboksilata. Dobijena jedinjenja su zatim korišćena kao polazna za sintezu sledećih amida: 2,6-dimetil-4-N3,N5-di(tiazol-2-il)-1,4dihidropiridin-3,5-dikarboksiamida, 2,6-dimetil-4-(3'-nitrofenil)-N3,N5-di(tiazol-2-il)-1,4-dihidropiridin-3,5-dikarboksiamida, 2,6dimetil-4-(4'-nitrofenil)-N3,N5-di(tiazol-2-il)-1,4-dihidropiridin-3,5dikarboksiamida, 4-(2'-hidroksifenil)-2,6-dimetil-N3,N5-di(tiazol-2il)-1,4-dihidropiridin-3,5-dikarboksiamida, 4-(3'-hidroksifenil)-2,6dimetil-N3,N5-di(tiazol-2-il)-1,4-dihidropiridin-3,5-dikarboksiamida i 4-(4'-hidroksifenil)-2,6-dimetil-N3,N5-di(tiazol-2-il)-1,4dihidropiridin-3,5-dikarboksiamida. Amidni derivati 2,6-dimetil-4supstituisane-1,4-dihidropiridin-3,5-dikarboksilne kiseline su sintetisani u cilju utvrđivanja uticaja tipa i položaja supstituenta u molekulu na antioksidativnu aktivnost. Iz ove serije, najnižu vrednost IC50, tj. najbolju antioksidativnu aktivnost je pokazao 4(2'-hidroksifenil)-2,6-dimetil-N3,N5-di(tiazol-2-il)-1,4dihidropiridin-3,5-dikarboksiamid, dok su zanemarljive vrednosti pokazali 2,6-dimetil-4-N3,N5-di(tiazol-2-il)-1,4-dihidropiridin-3,5dikarboksiamid i 2,6-dimetil-4-(3'-nitrofenil)-N3,N5-di(tiazol-2-il)-1,4-dihidropiridin-3,5-dikarboksiamid. Ispitivanje antioksidativne aktivnosti je izvršeno merenjem sposobnosti jedinjenja da hvataju slobodne radikale primenom metode inhibicije pomoću DPPH (1,1difenil-2-pikril-hidrazil) radikala. Sintetisana jedinjenja su okarakterisana temperaturom topljenja, elementalnom analizom i FT-IR spektroskopijom., Six ester and amide derivates of 2,6-dimethyl-4-(substituted)-1,4-dihydropyridine-3,5-dicarboxylic acid have been synthesized in this paper, including: diethyl 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5dicarboxylate, diethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, diethyl 2,6dimethyl-4-(4-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, diethyl 4-(2-hydroxyphenyl)-2,6dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, diethyl 4-(3-hydroxyphenyl)-2,6-dimethyl-1,4dihydropyridine-3,5-dicarboxylate and diethyl 4-(4-hydroxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5dicarboxylate. Obtained ester derivates were used afterwards as a starting compounds for synthesis of amide derivates, including: 2,6-dimethyl-4-phenyl-N3,N5-di(thiazol-2-yl)-1,4-dihydropyridine-3,5-dicarboxamide, 2,6dimethyl-4-(3-nitrophenyl)-N3,N5-di(thiazol-2-yl)-1,4-dihydropyridine-3,5-dicarboxamide, 2,6-dimethyl-4(4-nitrophenyl)-N3,N5-di(thiazol-2-yl)-1,4-dihydropyridine-3,5-dicarboxamide, 4-(2-hydroxyphenyl)-2,6dimethyl-N3,N5-di(thiazol-2-yl)-1,4-dihydropyridine-3,5-dicarboxamide, 4-(3-hydroxyphenyl)-2,6-dimethylN3,N5-di(thiazol-2-yl)-1,4-dihydropyridine-3,5-dicarboxamide and 4-(4-hydroxyphenyl)-2,6-dimethylN3,N5-di(thiazol-2-yl)-1,4-dihydropyridine-3,5-dicarboxamide. Obtained compounds were characterized by melting point, elementary analysis and FT-IR spectroscopy. In order to determine the effect of the substituent, the antioxidative activity assay of obtained 1,4dihydropyridines was performed by using the DPPH (1,1-diphenyl-2-picryl-hydrazyl) free radical scavenging method.", publisher = "University of East Sarajevo, Faculty of Technology", journal = "Journal of Engineering and Processing Management", title = "Sinteza, karakterizacija i ispitivanje antioksidativne aktivnosti estarskih i amidnih derivata 2,6-dimetil-4-supstituisane-1,4-dihidropiridin-3,5-dikarboksilne kiseline, Synthesis, characterization and antioxidative assay of ester and amide derivates of 2,6-dimethyl-4-(substituted)-1,4dihydropyridine-3,5-dicarboxylic acid", pages = "15-8", number = "2", volume = "10", doi = "10.7251/JEPM181002008M" }
Mijatović, T., Perić, M., Matović, L., Ristović, M.,& Drmanić, S.. (2018). Sinteza, karakterizacija i ispitivanje antioksidativne aktivnosti estarskih i amidnih derivata 2,6-dimetil-4-supstituisane-1,4-dihidropiridin-3,5-dikarboksilne kiseline. in Journal of Engineering and Processing Management University of East Sarajevo, Faculty of Technology., 10(2), 8-15. https://doi.org/10.7251/JEPM181002008M
Mijatović T, Perić M, Matović L, Ristović M, Drmanić S. Sinteza, karakterizacija i ispitivanje antioksidativne aktivnosti estarskih i amidnih derivata 2,6-dimetil-4-supstituisane-1,4-dihidropiridin-3,5-dikarboksilne kiseline. in Journal of Engineering and Processing Management. 2018;10(2):8-15. doi:10.7251/JEPM181002008M .
Mijatović, Tamara, Perić, Milica, Matović, Luka, Ristović, Marija, Drmanić, Saša, "Sinteza, karakterizacija i ispitivanje antioksidativne aktivnosti estarskih i amidnih derivata 2,6-dimetil-4-supstituisane-1,4-dihidropiridin-3,5-dikarboksilne kiseline" in Journal of Engineering and Processing Management, 10, no. 2 (2018):8-15, https://doi.org/10.7251/JEPM181002008M . .