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Some Aryl Sulfonyl Ester-Based Heterocyclic Schiff Bases: Synthesis, Structure Elucidation and Antioxidant Activity

Yıl 2021, , 2967 - 2978, 15.12.2021
https://doi.org/10.21597/jist.963129

Öz

In this research work, a series of heterocyclic Schiff base compounds bearing arylsulfonyl ester moiety (2a-i) were designed, synthesized, characterized by spectral techniques such as 1D NMR (1H and 13C), 2D NMR (COSY and HMQC), and FT-IR; and then examined their antioxidant activity was by using four different methods as DPPH, ABTS, CUPRAC, and β-carotenelinoleic acid assays. According to the results obtained, it determined that all synthesized molecules had antioxidant activity. In the DPPH assay, it was found that compound 2e (IC50: 96.23±0.02 μM/mL) demonstrated the antioxidant activity among all synthesized molecules. In ABTS assay, compounds 2e (IC50: 41.88±0.21 μM/mL) and 2g (IC50: 50.75±0.32 μM/mL) were determined to be the molecules with the activity, respectively. Compound 2e (IC50:73.49±0.00 μM/mL) indicated the best antioxidant activity in the CUPRAC assay compared to other synthesize molecules. In the β-carotene-linoleic acid assay, compound 2e (IC50: 58.79±0.58 μM/mL) displayed antioxidant activity than all other synthesized molecules. Compounds 2d (IC50: 74.17±0.22 μM/mL) and 2g (IC50: 66.06±0.13 μM/mL) indicated higher antioxidant activity than the remaining molecules in this series, except for compound 2e. In conclusion, it is thought that this study will contribute to the ongoing studies on the design and synthesis of new antioxidant agents.

Teşekkür

The author would like to thank Prof. Dr. Mehmet Öztürk for his help in determining the antioxidant activity and Lonemed Sağlık Ürünleri Ltd. and its Director Erhan Atilla for supplying Laboratory Glassware.

Kaynakça

  • Al-Rubaye BK, Al-Jeboori MJ, Potgieter H, 2021. Metal complexes of multidentate N2S2 heterocyclic Schiff-base ligands; formation, structural characterization and biological activity. In Journal of Physics: Conference Series (Vol. 1879, No. 2, p. 022074). IOP Publishing.
  • Antolovich M, Prenzler PD, Patsalides E, McDonald S, Robards K, 2002. Methods for testing antioxidant activity. Analyst, 127: 183-198.
  • Apak R, Güçlü K, Özyürek M, Karademir SE, 2004. Novel total antioxidant capacity index for dietary polyphenols and vitamins C and E, using their cupric ion reducing capability in the presence of neocuproine: CUPRAC method. Journal of Agricultural and Food Chemistry, 52(26): 7970-7981.
  • Baytop T, 1984. Türkiye’de Bitkilerle Tedavi. Istanbul University, Pharmacy Faculty Publication No.40, Virtual Printing, 384.
  • Blois MS, 1958. Antioxidant determinations by the use of a stable free radical. Nature, 181(4617): 1199-1200.
  • Bozkurt E, Sıcak Y, Oruç-Emre EE, İyidoğan AK, Öztürk M, 2020. Design and bioevaluation of novel hydrazide-hydrazones derived from 4-acetyl-N-substituted benzenesulfonamide. Russian Journal of Bioorganic Chemistry, 46(5): 702-714.
  • Camadan Y, Çiçek B, Adem Ş, Çalışır Ü, Akkemik E, 2021. Investigation of in vitro and in silico effects of some novel carbazole Schiff bases on human carbonic anhydrase isoforms I and II. Journal of Biomolecular Structure and Dynamics, 1-10.
  • Chen X, Yu M, 2006a. (E)-3-[(1,5-Dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-ylimino) methylene] phenyl 4-methylbenzenesulfonate. Acta Crystallographica Section E: Structure Reports Online, 62(12): 5525-5526.
  • Chen X, Yu M, 2006b. (E)-5-(1,5-Dimethyl-3-oxo-2-phenyl-2, 3-dihydro-1H-pyrazol-4-yliminomethyl)-2-methoxyphenyl benzenesulfonate. Acta Crystallographica Section E: Structure Reports Online, 62(10): 4592-4593.
  • Collado D, Perez-Inestrosa E, Suau, R, Navarrete JTL, 2006. Regioselective hydroxylation of phenols by simultaneous photochemical generation of phenol cation-radical and hydroxyl radical. Tetrahedron, 62(12): 2927-2935.
  • Freudenberg K, Hess H, 1926. Ein Verfahren zur Kennzeichnung verschiedenartiger Hydroxylgruppen. Seine Anwendung auf das Lignin. Justus Liebigs Annalen der Chemie, 448(1): 121-133.
  • Gutteridge JMC, 1994. Biological origin of free radicals, and mechanisms of antioxidant protection. Chemico-Biological Interactions, 91: 133-140.
  • Harmandar K, Saglam MF, Sengul IF, Ekineker G, Balcik-Ercin P, Göksel M, Atilla D, 2021. Novel triazole containing zinc (II) phthalocyanine Schiff bases: Determination of photophysical and photochemical properties for photodynamic cancer therapy. Inorganica Chimica Acta, 519: 120286.
  • Hashem HE, Mohamed EA, Farag AA, Negm NA, Azmy EA, 2021. New heterocyclic Schiff base‐metal complex: Synthesis, characterization, density functional theory study, and antimicrobial evaluation. Applied Organometallic Chemistry, e6322.
  • Iacopetta D, Ceramella J, Catalano A, Saturnino C, Bonomo MG, Franchini C, Sinicropi MS, 2021. Schiff bases: interesting scaffolds with promising antitumoral properties. Applied Sciences, 11(4): 1877-1897.
  • Karaaslan C, Kadri H, Coban T, Suzen S, Westwell AD, 2013. Synthesis and antioxidant properties of substituted 2-phenyl-1H-indoles. Bioorganic and Medicinal Chemistry Letters, 23(9): 2671-2674.
  • Kavitha K, 2021. Design, synthesis, characterization of antimicrobial activity of schiff bases of novel quinazolin-4-one derivatives. Research Journal of Pharmacy and Technology, 14: 466-470.
  • Lei X, Jalla A, Abou Shama MA, Stafford JM, Cao B, 2015. Chromatography-free and eco-friendly synthesis of aryl tosylates and mesylates. Synthesis, 47(17): 2578-2585.
  • Liu B, Zhang C, Zhou X, 2016. Access to phthalazinones via palladium-catalyzed three-component cycloamino-carbonylation of 2-formylaryl tosylates, hydrazines and CO. Tetrahedron, 72(50): 8282-8286.
  • Lotlikar OA, Dandekar SN, Ramana MMV, Ratho SV, 2021. Synthesis, molecular docking, in vitro anti-bacterial, and anti-cancer activities of some novel oxo-spiro chromene Schiff’s bases. Russian Journal of Bioorganic Chemistry, 47(1): 199-207.
  • Messasma Z, Aggoun D, Houchi S, Ourari A, Ouennoughi Y, Keffous F, Mahdadi R, 2021. Biological activities, DFT calculations and docking of imines tetradentates ligands, derived from salicylaldehydic compounds as metallo-beta-lactamase inhibitors. Journal of Molecular Structure, 1228: 129463.
  • Miller HE, 1971. A simplified method for the evaluation of antioxidants. Journal of the American Oil Chemists' Society, 48(2): 91-91.
  • Mohamed M, Abdelakder H, Abdellah B 2021. Microwave assisted synthesis of 4-aminophenol Schiff bases: DFT computations, QSAR/Drug-likeness proprieties and antibacterial screening. Journal of Molecular Structure, 130666.
  • Morsy NM, Hassan AS, Hafez TS., Mahran MR., Sadawe IA, Gbaj AM, 2021. Synthesis, antitumor activity, enzyme assay, DNA binding and molecular docking of Bis-Schiff bases of pyrazoles. Journal of the Iranian Chemical Society, 18(1): 47-59.
  • Motherwell WB, Vázquez S 2000. A concise approach to the preparation of 2-hydroxydiarylketones by an intramolecular acyl radical ipso substitution. Tetrahedron Letters, 41: 9667-9671.
  • Nadler C, Nadler A, Hansen C, Diederichsen U, 2015. A photocleavable auxiliary for extended native chemical ligation. European Journal of Organic Chemistry, 2015: 3095-3102.
  • Naureen B, Miana GA, Shahid K, Asghar M, Tanveer S, Sarwar A, 2021. Iron (III) and Zinc (II) monodentate Schiff base metal complexes: Synthesis, characterisation and biological activities. Journal of Molecular Structure, 1231: 129946.
  • Orlova N, Nikolajeva I, Pučkins A, Belyakov S, Kirilova E, 2021. Heterocyclic Schiff bases of 3-aminobenzanthrone and their reduced analogues: Synthesis, properties and spectroscopy. Molecules, 26(9): 2570.
  • Pham-Huy LA, He H, Pham-Huy C, 2008. Free radicals, antioxidants in disease and health. International Journal of Biomedical Science, 4: 89-96.
  • Piller FM, Metzger A, Schade MA, Haag BA, Gavryushin A, Knochel P, 2009. Preparation of polyfunctional arylmagnesium, arylzinc, and benzylic zinc reagents by using magnesium in the presence of LiCl. Chemistry–A European Journal, 15: 192-7202.
  • Puskullu MO, Shirinzadeh H, Nenni M, Gurer-Orhan H, Suzen S, 2016. Synthesis and evaluation of antioxidant activity of new quinoline-2-carbaldehyde hydrazone derivatives: bioisosteric melatonin analogues. Journal of Enzyme Inhibition and Medicinal Chemistry, 31: 121-125.
  • Re R, Pellegrini N, Proteggente A, Pannala A, Yang M, Rice-Evans C, 1999. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Biology and Medicine, 26: 1231-1237.
  • Reddy CR, Rao NN, Srikanth B, 2010. Total synthesis of a diarylheptanoid, Rhoiptelol B. European Journal of Organic Chemistry, 2010: 345-351.
  • Reddy MR, Mallireddigari MR, Cosenza SC, Pallela VR, Iqbal NM, Robell KA, Kang DA, Reddy EP, 2008. Design, synthesis, and biological evaluation of (E)-styrylbenzylsulfones as novel anticancer agents. Journal of Medicinal Chemistry, 51(1): 86-100.
  • Selvi G, Özdemir FA, Aykutoglu G, Özdemir N, Şerbetçi , Cetinkaya B, Dayan O, 2020. A neutral arene ruthenium (II) complex with a sulfonated N, O-chelating ligand: Synthesis, characterization, in vitro cytotoxicity and antibacterial activity. Polyhedron, 176: 114300.
  • Şener N, Özkinali S, Altunoglu YC, Yerlikaya S, Gökçe H, Zurnaci M, Gür M, Cengiz M, Baloglu C, Şener İ, 2021. Antiproliferative properties and structural analysis of newly synthesized Schiff bases bearing pyrazole derivatives and molecular docking studies. Journal of Molecular Structure, 1241: 130520.
  • Shukla SN, Gaur, P, Prasad M, Agarwal K, Kaur H, Setua DK, Mehmotra R, Prasad M, Srivastava, RS, 2010. Synthesis, spectroscopic characterization and antibacterial activity of some chlorosulphoxide Ruthenium (II) and Ruthenium (III) complexes of 4-(benzylideneamino)-1,2-dimethyl-2-phenyl-1,2-dihydropyrazole-3-one, Schiff base. Journal of the Chilean Chemical Society, 55:159-165.
  • Sıcak Y, 2021b. Design and antiproliferative and antioxidant activities of furan-based thiosemicarbazides and 1,2,4-triazoles: their structure-activity relationship and SwissADME predictions. Medicinal Chemistry Research, 30(8): 1557-1568.
  • Sıcak Y, Büyüksakallı H, Malkoçoğlu S, Özler MA. Öztürk M, 2017. Antioxidant, anticholinesterase inhibitory and tyrosinase inhibitory activities of Iris xanthospuria extracts growing in Köyceğiz region. Journal of Ongoing Chemical Research, 3(1): 22-31.
  • Sıcak Y, Oruç‐Emre EE, Öztürk M, Taşkın‐Tok T, Karaküçük‐Iyidoğan A, 2019. Novel fluorine‐containing chiral hydrazide‐hydrazones: Design, synthesis, structural elucidation, antioxidant and anticholinesterase activity, and in silico studies. Chirality, 31(8): 603-615.
  • Sıcak Y, Şahin-Yağlıoğlu A, Öztürk M, 2021a. Bioactivities and phenolic constituents relationship of Muğla thyme and pine honey of Turkey with the chemometric approach. Journal of Food Measurement and Characterization, 15: 3694-3707.
  • Srinivasan V, Khamrang T, Ponraj C, Saravanan D, Yamini R, Bera S, Jhonsi MA, 2021. Pyrene based Schiff bases: Synthesis, crystal structure, antibacterial and BSA binding studies. Journal of Molecular Structure, 1225: 129153.
  • Sumrra SH, Zafar W, Asghar ML, Mushtaq F, Raza MA, Nazar MF, Nadeem MA, Imran M, Mumtaz S, 2021. Computational investigation of molecular structures, spectroscopic properties, cholinesterase inhibition and antibacterial activities of triazole Schiff bases endowed metal chelates. Journal of Molecular Structure, 1238: 130382.
  • Suzen S, 2007. Heterocyclic Chemistry, Bioactive Heterocycles, Khan MTH, Ed., Berlin, Heidelberg: Springer-Verlag.
  • Tok F, Koçyiğit-Kaymakçıoğlu B, Sağlık BN, Levent S, Özkay Y, Kaplancıklı ZA, 2019. Synthesis and biological evaluation of new pyrazolone Schiff bases as monoamine oxidase and cholinesterase inhibitors. Bioorganic Chemistry, 84: 41-50.
  • Tokalı FS, Taslimi P, Usanmaz H, Karaman M, Şendil K, 2021. Synthesis, characterization, biological activity and molecular docking studies of novel schiff bases derived from thiosemicarbazide: Biochemical and computational approach. Journal of Molecular Structure, 1231: 129666.
  • Uttara B, Singh AV, Zamboni P, Mahajan RT, 2009. Oxidative stress and neurodegenerative diseases: a review of upstream and downstream antioxidant therapeutic options. Current Neuropharmacology, 27: 65-74.
  • Yadav JS, Pandurangam T, Reddy VB, Reddy BS, 2010. Total Synthesis of Rhoiptelol B. Synthesis, 2010: 4300-4306.
Yıl 2021, , 2967 - 2978, 15.12.2021
https://doi.org/10.21597/jist.963129

Öz

Kaynakça

  • Al-Rubaye BK, Al-Jeboori MJ, Potgieter H, 2021. Metal complexes of multidentate N2S2 heterocyclic Schiff-base ligands; formation, structural characterization and biological activity. In Journal of Physics: Conference Series (Vol. 1879, No. 2, p. 022074). IOP Publishing.
  • Antolovich M, Prenzler PD, Patsalides E, McDonald S, Robards K, 2002. Methods for testing antioxidant activity. Analyst, 127: 183-198.
  • Apak R, Güçlü K, Özyürek M, Karademir SE, 2004. Novel total antioxidant capacity index for dietary polyphenols and vitamins C and E, using their cupric ion reducing capability in the presence of neocuproine: CUPRAC method. Journal of Agricultural and Food Chemistry, 52(26): 7970-7981.
  • Baytop T, 1984. Türkiye’de Bitkilerle Tedavi. Istanbul University, Pharmacy Faculty Publication No.40, Virtual Printing, 384.
  • Blois MS, 1958. Antioxidant determinations by the use of a stable free radical. Nature, 181(4617): 1199-1200.
  • Bozkurt E, Sıcak Y, Oruç-Emre EE, İyidoğan AK, Öztürk M, 2020. Design and bioevaluation of novel hydrazide-hydrazones derived from 4-acetyl-N-substituted benzenesulfonamide. Russian Journal of Bioorganic Chemistry, 46(5): 702-714.
  • Camadan Y, Çiçek B, Adem Ş, Çalışır Ü, Akkemik E, 2021. Investigation of in vitro and in silico effects of some novel carbazole Schiff bases on human carbonic anhydrase isoforms I and II. Journal of Biomolecular Structure and Dynamics, 1-10.
  • Chen X, Yu M, 2006a. (E)-3-[(1,5-Dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-ylimino) methylene] phenyl 4-methylbenzenesulfonate. Acta Crystallographica Section E: Structure Reports Online, 62(12): 5525-5526.
  • Chen X, Yu M, 2006b. (E)-5-(1,5-Dimethyl-3-oxo-2-phenyl-2, 3-dihydro-1H-pyrazol-4-yliminomethyl)-2-methoxyphenyl benzenesulfonate. Acta Crystallographica Section E: Structure Reports Online, 62(10): 4592-4593.
  • Collado D, Perez-Inestrosa E, Suau, R, Navarrete JTL, 2006. Regioselective hydroxylation of phenols by simultaneous photochemical generation of phenol cation-radical and hydroxyl radical. Tetrahedron, 62(12): 2927-2935.
  • Freudenberg K, Hess H, 1926. Ein Verfahren zur Kennzeichnung verschiedenartiger Hydroxylgruppen. Seine Anwendung auf das Lignin. Justus Liebigs Annalen der Chemie, 448(1): 121-133.
  • Gutteridge JMC, 1994. Biological origin of free radicals, and mechanisms of antioxidant protection. Chemico-Biological Interactions, 91: 133-140.
  • Harmandar K, Saglam MF, Sengul IF, Ekineker G, Balcik-Ercin P, Göksel M, Atilla D, 2021. Novel triazole containing zinc (II) phthalocyanine Schiff bases: Determination of photophysical and photochemical properties for photodynamic cancer therapy. Inorganica Chimica Acta, 519: 120286.
  • Hashem HE, Mohamed EA, Farag AA, Negm NA, Azmy EA, 2021. New heterocyclic Schiff base‐metal complex: Synthesis, characterization, density functional theory study, and antimicrobial evaluation. Applied Organometallic Chemistry, e6322.
  • Iacopetta D, Ceramella J, Catalano A, Saturnino C, Bonomo MG, Franchini C, Sinicropi MS, 2021. Schiff bases: interesting scaffolds with promising antitumoral properties. Applied Sciences, 11(4): 1877-1897.
  • Karaaslan C, Kadri H, Coban T, Suzen S, Westwell AD, 2013. Synthesis and antioxidant properties of substituted 2-phenyl-1H-indoles. Bioorganic and Medicinal Chemistry Letters, 23(9): 2671-2674.
  • Kavitha K, 2021. Design, synthesis, characterization of antimicrobial activity of schiff bases of novel quinazolin-4-one derivatives. Research Journal of Pharmacy and Technology, 14: 466-470.
  • Lei X, Jalla A, Abou Shama MA, Stafford JM, Cao B, 2015. Chromatography-free and eco-friendly synthesis of aryl tosylates and mesylates. Synthesis, 47(17): 2578-2585.
  • Liu B, Zhang C, Zhou X, 2016. Access to phthalazinones via palladium-catalyzed three-component cycloamino-carbonylation of 2-formylaryl tosylates, hydrazines and CO. Tetrahedron, 72(50): 8282-8286.
  • Lotlikar OA, Dandekar SN, Ramana MMV, Ratho SV, 2021. Synthesis, molecular docking, in vitro anti-bacterial, and anti-cancer activities of some novel oxo-spiro chromene Schiff’s bases. Russian Journal of Bioorganic Chemistry, 47(1): 199-207.
  • Messasma Z, Aggoun D, Houchi S, Ourari A, Ouennoughi Y, Keffous F, Mahdadi R, 2021. Biological activities, DFT calculations and docking of imines tetradentates ligands, derived from salicylaldehydic compounds as metallo-beta-lactamase inhibitors. Journal of Molecular Structure, 1228: 129463.
  • Miller HE, 1971. A simplified method for the evaluation of antioxidants. Journal of the American Oil Chemists' Society, 48(2): 91-91.
  • Mohamed M, Abdelakder H, Abdellah B 2021. Microwave assisted synthesis of 4-aminophenol Schiff bases: DFT computations, QSAR/Drug-likeness proprieties and antibacterial screening. Journal of Molecular Structure, 130666.
  • Morsy NM, Hassan AS, Hafez TS., Mahran MR., Sadawe IA, Gbaj AM, 2021. Synthesis, antitumor activity, enzyme assay, DNA binding and molecular docking of Bis-Schiff bases of pyrazoles. Journal of the Iranian Chemical Society, 18(1): 47-59.
  • Motherwell WB, Vázquez S 2000. A concise approach to the preparation of 2-hydroxydiarylketones by an intramolecular acyl radical ipso substitution. Tetrahedron Letters, 41: 9667-9671.
  • Nadler C, Nadler A, Hansen C, Diederichsen U, 2015. A photocleavable auxiliary for extended native chemical ligation. European Journal of Organic Chemistry, 2015: 3095-3102.
  • Naureen B, Miana GA, Shahid K, Asghar M, Tanveer S, Sarwar A, 2021. Iron (III) and Zinc (II) monodentate Schiff base metal complexes: Synthesis, characterisation and biological activities. Journal of Molecular Structure, 1231: 129946.
  • Orlova N, Nikolajeva I, Pučkins A, Belyakov S, Kirilova E, 2021. Heterocyclic Schiff bases of 3-aminobenzanthrone and their reduced analogues: Synthesis, properties and spectroscopy. Molecules, 26(9): 2570.
  • Pham-Huy LA, He H, Pham-Huy C, 2008. Free radicals, antioxidants in disease and health. International Journal of Biomedical Science, 4: 89-96.
  • Piller FM, Metzger A, Schade MA, Haag BA, Gavryushin A, Knochel P, 2009. Preparation of polyfunctional arylmagnesium, arylzinc, and benzylic zinc reagents by using magnesium in the presence of LiCl. Chemistry–A European Journal, 15: 192-7202.
  • Puskullu MO, Shirinzadeh H, Nenni M, Gurer-Orhan H, Suzen S, 2016. Synthesis and evaluation of antioxidant activity of new quinoline-2-carbaldehyde hydrazone derivatives: bioisosteric melatonin analogues. Journal of Enzyme Inhibition and Medicinal Chemistry, 31: 121-125.
  • Re R, Pellegrini N, Proteggente A, Pannala A, Yang M, Rice-Evans C, 1999. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Biology and Medicine, 26: 1231-1237.
  • Reddy CR, Rao NN, Srikanth B, 2010. Total synthesis of a diarylheptanoid, Rhoiptelol B. European Journal of Organic Chemistry, 2010: 345-351.
  • Reddy MR, Mallireddigari MR, Cosenza SC, Pallela VR, Iqbal NM, Robell KA, Kang DA, Reddy EP, 2008. Design, synthesis, and biological evaluation of (E)-styrylbenzylsulfones as novel anticancer agents. Journal of Medicinal Chemistry, 51(1): 86-100.
  • Selvi G, Özdemir FA, Aykutoglu G, Özdemir N, Şerbetçi , Cetinkaya B, Dayan O, 2020. A neutral arene ruthenium (II) complex with a sulfonated N, O-chelating ligand: Synthesis, characterization, in vitro cytotoxicity and antibacterial activity. Polyhedron, 176: 114300.
  • Şener N, Özkinali S, Altunoglu YC, Yerlikaya S, Gökçe H, Zurnaci M, Gür M, Cengiz M, Baloglu C, Şener İ, 2021. Antiproliferative properties and structural analysis of newly synthesized Schiff bases bearing pyrazole derivatives and molecular docking studies. Journal of Molecular Structure, 1241: 130520.
  • Shukla SN, Gaur, P, Prasad M, Agarwal K, Kaur H, Setua DK, Mehmotra R, Prasad M, Srivastava, RS, 2010. Synthesis, spectroscopic characterization and antibacterial activity of some chlorosulphoxide Ruthenium (II) and Ruthenium (III) complexes of 4-(benzylideneamino)-1,2-dimethyl-2-phenyl-1,2-dihydropyrazole-3-one, Schiff base. Journal of the Chilean Chemical Society, 55:159-165.
  • Sıcak Y, 2021b. Design and antiproliferative and antioxidant activities of furan-based thiosemicarbazides and 1,2,4-triazoles: their structure-activity relationship and SwissADME predictions. Medicinal Chemistry Research, 30(8): 1557-1568.
  • Sıcak Y, Büyüksakallı H, Malkoçoğlu S, Özler MA. Öztürk M, 2017. Antioxidant, anticholinesterase inhibitory and tyrosinase inhibitory activities of Iris xanthospuria extracts growing in Köyceğiz region. Journal of Ongoing Chemical Research, 3(1): 22-31.
  • Sıcak Y, Oruç‐Emre EE, Öztürk M, Taşkın‐Tok T, Karaküçük‐Iyidoğan A, 2019. Novel fluorine‐containing chiral hydrazide‐hydrazones: Design, synthesis, structural elucidation, antioxidant and anticholinesterase activity, and in silico studies. Chirality, 31(8): 603-615.
  • Sıcak Y, Şahin-Yağlıoğlu A, Öztürk M, 2021a. Bioactivities and phenolic constituents relationship of Muğla thyme and pine honey of Turkey with the chemometric approach. Journal of Food Measurement and Characterization, 15: 3694-3707.
  • Srinivasan V, Khamrang T, Ponraj C, Saravanan D, Yamini R, Bera S, Jhonsi MA, 2021. Pyrene based Schiff bases: Synthesis, crystal structure, antibacterial and BSA binding studies. Journal of Molecular Structure, 1225: 129153.
  • Sumrra SH, Zafar W, Asghar ML, Mushtaq F, Raza MA, Nazar MF, Nadeem MA, Imran M, Mumtaz S, 2021. Computational investigation of molecular structures, spectroscopic properties, cholinesterase inhibition and antibacterial activities of triazole Schiff bases endowed metal chelates. Journal of Molecular Structure, 1238: 130382.
  • Suzen S, 2007. Heterocyclic Chemistry, Bioactive Heterocycles, Khan MTH, Ed., Berlin, Heidelberg: Springer-Verlag.
  • Tok F, Koçyiğit-Kaymakçıoğlu B, Sağlık BN, Levent S, Özkay Y, Kaplancıklı ZA, 2019. Synthesis and biological evaluation of new pyrazolone Schiff bases as monoamine oxidase and cholinesterase inhibitors. Bioorganic Chemistry, 84: 41-50.
  • Tokalı FS, Taslimi P, Usanmaz H, Karaman M, Şendil K, 2021. Synthesis, characterization, biological activity and molecular docking studies of novel schiff bases derived from thiosemicarbazide: Biochemical and computational approach. Journal of Molecular Structure, 1231: 129666.
  • Uttara B, Singh AV, Zamboni P, Mahajan RT, 2009. Oxidative stress and neurodegenerative diseases: a review of upstream and downstream antioxidant therapeutic options. Current Neuropharmacology, 27: 65-74.
  • Yadav JS, Pandurangam T, Reddy VB, Reddy BS, 2010. Total Synthesis of Rhoiptelol B. Synthesis, 2010: 4300-4306.
Toplam 48 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Kimya Mühendisliği
Bölüm Kimya / Chemistry
Yazarlar

Eyüp Başaran 0000-0002-7840-5919

Yayımlanma Tarihi 15 Aralık 2021
Gönderilme Tarihi 6 Temmuz 2021
Kabul Tarihi 20 Eylül 2021
Yayımlandığı Sayı Yıl 2021

Kaynak Göster

APA Başaran, E. (2021). Some Aryl Sulfonyl Ester-Based Heterocyclic Schiff Bases: Synthesis, Structure Elucidation and Antioxidant Activity. Journal of the Institute of Science and Technology, 11(4), 2967-2978. https://doi.org/10.21597/jist.963129
AMA Başaran E. Some Aryl Sulfonyl Ester-Based Heterocyclic Schiff Bases: Synthesis, Structure Elucidation and Antioxidant Activity. Iğdır Üniv. Fen Bil Enst. Der. Aralık 2021;11(4):2967-2978. doi:10.21597/jist.963129
Chicago Başaran, Eyüp. “Some Aryl Sulfonyl Ester-Based Heterocyclic Schiff Bases: Synthesis, Structure Elucidation and Antioxidant Activity”. Journal of the Institute of Science and Technology 11, sy. 4 (Aralık 2021): 2967-78. https://doi.org/10.21597/jist.963129.
EndNote Başaran E (01 Aralık 2021) Some Aryl Sulfonyl Ester-Based Heterocyclic Schiff Bases: Synthesis, Structure Elucidation and Antioxidant Activity. Journal of the Institute of Science and Technology 11 4 2967–2978.
IEEE E. Başaran, “Some Aryl Sulfonyl Ester-Based Heterocyclic Schiff Bases: Synthesis, Structure Elucidation and Antioxidant Activity”, Iğdır Üniv. Fen Bil Enst. Der., c. 11, sy. 4, ss. 2967–2978, 2021, doi: 10.21597/jist.963129.
ISNAD Başaran, Eyüp. “Some Aryl Sulfonyl Ester-Based Heterocyclic Schiff Bases: Synthesis, Structure Elucidation and Antioxidant Activity”. Journal of the Institute of Science and Technology 11/4 (Aralık 2021), 2967-2978. https://doi.org/10.21597/jist.963129.
JAMA Başaran E. Some Aryl Sulfonyl Ester-Based Heterocyclic Schiff Bases: Synthesis, Structure Elucidation and Antioxidant Activity. Iğdır Üniv. Fen Bil Enst. Der. 2021;11:2967–2978.
MLA Başaran, Eyüp. “Some Aryl Sulfonyl Ester-Based Heterocyclic Schiff Bases: Synthesis, Structure Elucidation and Antioxidant Activity”. Journal of the Institute of Science and Technology, c. 11, sy. 4, 2021, ss. 2967-78, doi:10.21597/jist.963129.
Vancouver Başaran E. Some Aryl Sulfonyl Ester-Based Heterocyclic Schiff Bases: Synthesis, Structure Elucidation and Antioxidant Activity. Iğdır Üniv. Fen Bil Enst. Der. 2021;11(4):2967-78.