Sinteza i biološka svojstva nekih azo boja na bazi 3-cijano-6-hidroksi-4-metil-1-propil-2-piridona
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Jul 13, 2021
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Apstrakt
Azo boje su najznačajnija grupa organskih sintetskih boja. Visoki molarni ekstencioni koeficijenti, koji karakterišu azo jedinjena, doprinose njihovoj širokoj upotrebi kako u tradicionalnom bojenju materijala, tako i sve većoj primeni u novijim tehnologijama kao što su optički materijali i solarne ćelije. Mnoga istraživanja pokazuju da azo boje dobijene iz heterocikličnih molekula imaju biološku aktivnost. Arilazo piridonske boje pripadaju klasi disperznih boja koje ispoljavaju antibakterijsku, antifungalnu, antikancerogenu i antioksidativnu aktivnost. U ovom radu sintetisane su tri azo boje polazeći iz 2-, 3– i 4-aminofenola i 3-cijano-6-hidroksi-4-metil-1-propil-2-piridona. Struktura jedinjenja potvrđena je ATR-FTIR, NMR i UV-Vis podacima. Antioksidsativna aktivnost jedinjenja ispitana je ABTS metodom. Fizičko-hemijski deskriptori i ADME parametari određeni su in silico pomoću SwissADME programa.
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Kako citirati
TADIĆ, Julijana et al.
Sinteza i biološka svojstva nekih azo boja na bazi 3-cijano-6-hidroksi-4-metil-1-propil-2-piridona.
Zbornik Međunarodnog kongresa o procesnoj industriji – Procesing, [S.l.], v. 34, n. 1, p. 83-88, july 2021.
Dostupno na: <https://izdanja.smeits.rs/index.php/ptk/article/view/6571>. Datum pristupa: 27 jan. 2022
Sekcija
Procesne tehnologije
Reference
Zollinger H. Color chemistry: synthesis, properties and application of organic dyes and pigments. Weinheim: Wiley-VCH; 2003.
[2] Porobić SJ, Krstić AD, Jovanović DJ, Lađarević JM, Katnić ĐB, Mijin DŽ, Marinović-Cincović M. Synthesis and thermal properties of arylazo pyridone dyes. Dyes Pigments 2019;170:107602. https://doi.org/https://doi.org/10.1016/j.dyepig.2019.107602.
[3] Wainwright M. Dyes in the development of drugs and pharmaceuticals. Dyes Pigments 2008;76:582–9. https://doi.org/https://doi.org/10.1016/j.dyepig.2007.01.015.
[4] Tadić JD, Lađarević JM, Vitnik ŽJ, Vitnik VD, Stanojković TP, Matić IZ, Mijin DŽ. Novel azo pyridone dyes based on dihydropyrimidinone skeleton: Synthesis, DFT study and anticancer activity. Dyes Pigments 2021;187:109123. https://doi.org/https://doi.org/10.1016/j.dyepig.2020.109123.
[5] Ashkar SM, El-Apasery MA, Touma MM, Elnagdi MH. Synthesis of some novel biologically active disperse dyes derived from 4-methyl-2,6-dioxo-1-propyl-1,2,5,6-tetrahydropyridine- 3-carbonitrile as coupling component and their colour assessment on polyester fabrics. Molecules 2012;17:8822–31. https://doi.org/10.3390/molecules17088822.
[6] Bendary E, Francis RR, Ali HMG, Sarwat MI, El Hady S. Antioxidant and structure–activity relationships (SARs) of some phenolic and anilines compounds. Ann Agric Sci 2013;58:173–81. https://doi.org/https://doi.org/10.1016/j.aoas.2013.07.002.
[7] Tadić J, Mihajlović M, Jovanović M, Mijin D. Continuous flow synthesis of some 6- and 1,6-substituted 3-cyano-4-methyl-2-pyridones. J Serb Chem Soc 2019;84:531–8. https://doi.org/10.2298/JSC180703092T.
[8] Re R, Pellegrini N, Proteggente A, Pannala A, Yang M, Rice-Evans C. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Biol Med 1999;26:1231–7. https://doi.org/10.1016/S0891-5849(98)00315-3.
[9] A free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendli-ness, www.swiss.ch; Swiss Institute of Bioinformatics 2019 [accessed April 2021].
[10] Mirković J, Rogan J, Poleti D, Vitnik V, Vitnik Ž, Ušćumlić G, Mijin D. On the structures of 5-(4-, 3- and 2-methoxyphenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone: An experi-mental and theoretical study. Dyes Pigments 2014;104:160–8. https://doi.org/https://doi.org/10.1016/j.dyepig.2014.01.007.
[11] Mirković J, Božić B, Vitnik V, Vitnik Ž, Rogan J, Poleti D, Ušćumlić G, Mijin D. Structural, spectroscopic and computational study of 5-(substituted phenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridones. Color Technol 2017;134:33–43. https://doi.org/10.1111/cote.12321.
[12] Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. Experimental and computational ap-proaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliver Rev 1997;23:3–25. https://doi.org/https://doi.org/10.1016/S0169-409X(96)00423-1.
[13] Ismail MMF, Farrag AM, Harras MF, Ibrahim MH, Mehany ABM. Apoptosis: A target for anticancer therapy with novel cyanopyridines. Bioorg Chem 2020;94:103481. https://doi.org/10.1016/j.bioorg.2019.103481.
[2] Porobić SJ, Krstić AD, Jovanović DJ, Lađarević JM, Katnić ĐB, Mijin DŽ, Marinović-Cincović M. Synthesis and thermal properties of arylazo pyridone dyes. Dyes Pigments 2019;170:107602. https://doi.org/https://doi.org/10.1016/j.dyepig.2019.107602.
[3] Wainwright M. Dyes in the development of drugs and pharmaceuticals. Dyes Pigments 2008;76:582–9. https://doi.org/https://doi.org/10.1016/j.dyepig.2007.01.015.
[4] Tadić JD, Lađarević JM, Vitnik ŽJ, Vitnik VD, Stanojković TP, Matić IZ, Mijin DŽ. Novel azo pyridone dyes based on dihydropyrimidinone skeleton: Synthesis, DFT study and anticancer activity. Dyes Pigments 2021;187:109123. https://doi.org/https://doi.org/10.1016/j.dyepig.2020.109123.
[5] Ashkar SM, El-Apasery MA, Touma MM, Elnagdi MH. Synthesis of some novel biologically active disperse dyes derived from 4-methyl-2,6-dioxo-1-propyl-1,2,5,6-tetrahydropyridine- 3-carbonitrile as coupling component and their colour assessment on polyester fabrics. Molecules 2012;17:8822–31. https://doi.org/10.3390/molecules17088822.
[6] Bendary E, Francis RR, Ali HMG, Sarwat MI, El Hady S. Antioxidant and structure–activity relationships (SARs) of some phenolic and anilines compounds. Ann Agric Sci 2013;58:173–81. https://doi.org/https://doi.org/10.1016/j.aoas.2013.07.002.
[7] Tadić J, Mihajlović M, Jovanović M, Mijin D. Continuous flow synthesis of some 6- and 1,6-substituted 3-cyano-4-methyl-2-pyridones. J Serb Chem Soc 2019;84:531–8. https://doi.org/10.2298/JSC180703092T.
[8] Re R, Pellegrini N, Proteggente A, Pannala A, Yang M, Rice-Evans C. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Biol Med 1999;26:1231–7. https://doi.org/10.1016/S0891-5849(98)00315-3.
[9] A free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendli-ness, www.swiss.ch; Swiss Institute of Bioinformatics 2019 [accessed April 2021].
[10] Mirković J, Rogan J, Poleti D, Vitnik V, Vitnik Ž, Ušćumlić G, Mijin D. On the structures of 5-(4-, 3- and 2-methoxyphenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone: An experi-mental and theoretical study. Dyes Pigments 2014;104:160–8. https://doi.org/https://doi.org/10.1016/j.dyepig.2014.01.007.
[11] Mirković J, Božić B, Vitnik V, Vitnik Ž, Rogan J, Poleti D, Ušćumlić G, Mijin D. Structural, spectroscopic and computational study of 5-(substituted phenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridones. Color Technol 2017;134:33–43. https://doi.org/10.1111/cote.12321.
[12] Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. Experimental and computational ap-proaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliver Rev 1997;23:3–25. https://doi.org/https://doi.org/10.1016/S0169-409X(96)00423-1.
[13] Ismail MMF, Farrag AM, Harras MF, Ibrahim MH, Mehany ABM. Apoptosis: A target for anticancer therapy with novel cyanopyridines. Bioorg Chem 2020;94:103481. https://doi.org/10.1016/j.bioorg.2019.103481.