Synthesis of New Ligands Containing Azomethine Group and Investigation of Antioxidant, Antiurease Activities
Yıl: 2020 Cilt: 33 Sayı: 3 Sayfa Aralığı: 662 - 671 Metin Dili: İngilizce DOI: 10.35378/gujs. 615818 İndeks Tarihi: 29-07-2022
Synthesis of New Ligands Containing Azomethine Group and Investigation of Antioxidant, Antiurease Activities
Öz: A series of Schiff base ligands containing 1,2,4-triazole ring were obtained by the addition ofaldehydes to the amino compound under mild conditions in 80–82% yields. A reduction of theseligands with sodium borohydride resulted in Schiff base reduction products. New ligands wereinvestigated for their antioxidant activities such as DPPH (2,2-diphenyl-1-picrylhydrazyl), ABTS(2,2’-azino-bis (3-ethylbenzo-thizoline-6-sulphonic acid) diammonium salt) radical scavengingand reducing power. 1H and 13C-NMR spectra (δ, ppm) were observed on a Varian Mercury 200MHz spectrophotometer as standard substance using tetramethylsilane Match constants (Jvalues) were given as Hertz. NMR coefficients are truncated as follows: s=singlet, d=dublet,t=triplet, m=multiplet signal. Combustion analysis was performed on a Carlo Erba 1106 elementalanalyzer. All the compounds gave C, H, and N analysis results within ±0.6 % of the theoreticalvalues. The IR spectra (υ, cm−1) were viewed with a Perkin-Elmer 1600 FTIR spectrometer inKBr pellets.
Anahtar Kelime: Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık
- Carter, M.J., Rillema, D.P., Basolo, F.J., “Oxygen carrier and redox properties of some neutral cobalt chelates. Axial and in-plane ligand effects”, Am. Chem. Soc., 96: 392-400, (1974).
- Asada, H., Hayashi, K., Negoro, S., Fujiwara, M., Matsushita, T., “Preparation and structures of tri nuclear manganese (II) complexes with N-2-pyridiylmethylidene-2-hydroxy-5-substitutedphenylamine”, Inorg. Chem. Commun., 6: 193-196, (2003).
- Saghatforoush, L., Aminkhani, A., Ershad, S., Karimnezhad, G., Ghammamy, S., Kabiri, R., “Preparation of Zinc (II) and Cadmium (II) Complexes of the Tetradentate Schiff Base Ligand 2-((E)- (2-(2-(pyridine-2-yl)-ethylthio)ethylimino)methyl)-4-bromophenol (PytBrsalH)”, Molecules, 13: 804- 811, (2008).
- Li, S., Chen, S., Ma, H., Yu, R., Liu, D.,“Investigation on some Schiff bases as HCl corrosioninhibitors for copper”, Corros. Sci., 41: 1273-1287, (1999).
- Khalifa, K.M., Maihub, A.A., El-Ajaily, M.M., Mobain, S.A., “Coordination Trends of 6-Amino-4- hydroxy-2-mercaptopyrimidine Towards Co (II), Ni (II) and Cu (II) Ions”, J. Chem. Soc. Pak., 32: 650- 653, (2010). Unaleroglu, C., Temelli, B., Hokelek, T., “Conformational and structural analysis of N-N′-bis(4- methoxybenzylidene)ethylenediamine”, J. Mol. Struct., 570: 91-95, (2001).
- Barba, V., Santillan, R., Farfan, N., “Dimeric Boronates Derived from the Reaction of Schiff Bases and Boronic Acids”, J. Braz. Chem. Soc., 16: 449-455, (2005).
- Chen, W., Ou, W., Wang, L., Hao, Y., Cheng, J., Li, J., Liu, Y.N., “Synthesis and biological evaluation of hydroxyl-substituted Schiff-bases containing ferrocenyl moieties”, Dalton Trans. 42: 15678-15686, (2013).
- Cheng, L., Tang, -X., Luo, X., Jin, -L., Dai, F., Yang, J., Y.-P. Qian, Li, X.-Z., Zhou, B., “Antioxidant and antiproliferative activities of hydroxyl-substituted Schiff bases”, Bioorg. Med. Chem. Lett., 20: 2417-2420, (2010).
- Norman, D.W., Edwards, J.P., Vogels, C.M., Decken, A.S., Westcott, A., “Synthesis and reactivity of novel Schiff bases containing boronate esters”, Can. J. Chem., 80: 31-40, (2002).
- Singh, R.V., Biyala, M.K., “Structural studies with antimicrobial and antifertility activity of a monofunctional bidentate ligand with its boron(III), palladium(II), and platinum(II) complexes”, Phosphorus Sulfur Silicon Relat. Elem., 181: 1477-1491, (2006).
- Hou, A., Zhang, C., Wang, Y., “Preparation and UV-protective properties of functional cellulose fabrics based on reactive azobenzene Schiff base derivative”, Carbohydr. Polym., 87: 284-288, (2012).
- Farag, A.M., Siang, T.G., Osman, H., Eltayeb, N.E., Khadeer Ahamed, M.B., Abdul Majid, A.M.S., Balal, I.A.A., “Synthesis, characterizationand in vitro cytotoxic properties of some novel Schiff base metal complexes in HepG2 cells”, World Appl. Sci. J., 11: 1196–1209, (2010).
- Sarı, N., Yüzüak, N., “Synthesis and characterization of novel polymeric-schiff bases and their complexes”, J. Inorg. Organomet. Polym. Mater., 16: 259-269, (2006). Rice-Evans, C.A., Diplock, A.T., Symons, M.C.R., Techniques in Free Radical Research 1st ed., Elsevier, Amsterdam, (1991).
- Griendling, K.K., FitzGerald, G.A., “Oxidative stress and cardiovascular injury: Part I: basic mechanisms and in vivo monitoring of ROS”, Circulation, 108: 1912-1916, (2003).
- Reuter, S., Gupta, C.S., Chaturvedi, M.M., Aggarwal, B.B. “Oxidative stress, inflammation, and cancer: How are they linked?”, Free Radic. Biol. Med., 49: 1603-1616, (2010).
- Nihro, S.Y., Ueda, T., Miki, H., Matsomota, H., Satoh, T., “Protective effects of hydroxychalcones on free radical-induced cell damage”, Biol. Pharm. Bull., 17: 251-256, (1994).
- Zerner, B., “Recent advances in the chemistry of an old enzyme, urease”, Bioorg. Chem., 19: 116-131, (1991).
- Krajewska, B., Van-Eldik, R., Brindell, M., “Temperature- and pressure-dependent stopped-flow kinetic studies of jack bean urease”, Implications for the catalytic mechanism, J. Biol. Inorg. Chem., 17: 1123-1134, (2012).
- Mobley, H.L.T., Island, M.D., Hausinger, R.P., “Molecular biology of microbial ureases”, Microbiol. Rev., 59: 451-480, (1995).
- Mobley, H.L.T., Island, M.D., Hausinger, R.P., “Molecular biology of microbial ureases”, Microbiol. Rev., 59: 451-480, (1995).
- Warren, J.R. Marshall, B., “Unidentified curved bacilli on gastric epithelium in active chronic gastritis”, Lancet., 1: 1273-1275, (1983).
- Maroney, M., Ciurli, J. S., “Nonredox Nickel Enzymes”, Chem. Rev., 114: 4206-4228, (2014).
- Mazzei, L., Cianci, M., Benini, S., Bertini, L., Musiani, F. Ciurli, S., “Inactivation of urease by 1, 4- benzoquinone: chemistry at the protein surface”, J. Inorg. Biochem., 154: 42-49, (2016).
- Gumrukcuoglu, N., Serdar, M., Celik, E., Sevim, A., Demirbas, N., “Synthesis and Antimicrobial Activities of Some New 1, 2, 4-Triazole Derivatives”, Turk. J. Chem., 31: 335-348, (2007).
- Brand-Williams, W., Cuvelier, M.W. and Berset, C., “Use of a free radical method to evaluate antioxidant activity”, LWT-Food Sci. Technol., 28: 25-30, (1995).
- Arnao, M.B., Cano, A., Acosta, M., “The hydrophilic and lipophilic contribution to total antioxidant activity”, Food Chem., 73: 239-244, (2001).
- Oyaizu, M., “Studies on Products of Browning Reaction”, Japan. J. Nutr., 44: 307-315, (1986).
- Van Slyke, D.D. and Archibald, R.M., “Manometric, Titrimetric and Colorimetric Methods for Measurement of Urease Activity”, BJ. Biol. Chem., 154: 623-642, (1944).
- Nelson, S.M., Knox, C.V., Cann Drew, M.Mc., “Metal-ion-controlled transamination in the synthesis of macrocyclic Schiff-base ligands. Part I. Reactions of 2, 6-diacetylpyridine and dicarbonyl compounds with 3, 6-dioxaoctane-1,8-diamine”, J. Chem. Soc. Dalton Trans., 8: 1669-1677, (1981).
- Gumrukcuoglu, N., Ugras, S., Ugras, H.I., Cakir, U., “Synthesis, extraction and antibacterial studies of some new bis-1,2,4-triazole derivatives part II”, J. Incl. Phenom. Macrocycl. Chem., 73: 359-367, (2012).
- Meir, S., Kanner, J., Akiri, B., Hadas, S.P., “Determinating and involvement of aqueus reducing compounds in oxidative defense systems of various senescing leaves”, J. Agric. Food Chem., 43: 1813- 1819, (1995).
- Gumrukcuoglu, N., Bilgin Sokmen, B., Ugras, S., Ugras, H. I., Yanardag, R. “Synthesis, antibacterial, antielastase, antiurease and antioxidant activities of new 1,4-butylene bridged bis-1,2,4-triazole derivatives”, J. Enzyme Inh. Med. Chem., 28: 89–94, (2013).
- Yamaguchi T, Takamura H, Matoba T, Terao J. HPLC method for evaluation of the free radicalscavenging activity of foods by using 1,1-diphenyl-2-picrylhydrazyl. Biosci. Biotechnol. Biochem., 62: 1201–1204, (1998).
- Bilgin Sokmen, B., Gumrukcuoglu, N., Ugras, S., Sahin, H., Sagkal, Y., Ugras, H.I., “Synthesis, Antibacterial, Antiurease, and Antioxidant Activities of Some New 1,2,4-Triazole Schiff Base and Amine Derivatives”, Appl. Biochem. Biotech, 175: 705-714, (2015).
- Bilgin Sokmen, B., Gumrukcuoglu, N., Ugras, S., Ugras, H. I., Yanardag, R. “Synthesis, antibacterial, antielastase, antiurease and antioxidant activities of new methoxy substitued bis-1,2,4-triazole derivatives”, J. Enzyme Inh. Med. Chem., 28: 72–77, (2013).
- Khan, I., Ali, S., Hameed, S., Rama, N.H., Hussain, M.T., Wadood, A., et al. “Synthesis, antioxidant activities and urease inhibition of some new 1,2,4-triazole and 1,3,4-thiadiazole derivatives”, Eur. J. Med. Chem., 45: 5200–5207, (2010).
- Pombeiro, A. J. L., Kukushkin, V. Yu., “Comprehensive Coordination Chemistry II”, J.A. McCleverty and T.J. Meyer, Eds.; Elsevier-PergamonPress, Oxford, New York, 1: 585 (2003).
- Kukushkin, V. Yu., Pombeiro, A. J. L., Additions to Metal-Activated Organonitriles Chem. Rev., 102: 1771-1802, (2002). Steed, J. W., Atwood, J. L., “Definition and Emergence of Supramolecular Chemistry Adapted in part from Supramolecular Chem”, Wiley: Chichester, 2nd Ed., 2009.
| APA | gümrükçüoğlu n, Bilgin Sökmen B (2020). Synthesis of New Ligands Containing Azomethine Group and Investigation of Antioxidant, Antiurease Activities. , 662 - 671. 10.35378/gujs. 615818 |
| Chicago | gümrükçüoğlu nurhan,Bilgin Sökmen Bahar Synthesis of New Ligands Containing Azomethine Group and Investigation of Antioxidant, Antiurease Activities. (2020): 662 - 671. 10.35378/gujs. 615818 |
| MLA | gümrükçüoğlu nurhan,Bilgin Sökmen Bahar Synthesis of New Ligands Containing Azomethine Group and Investigation of Antioxidant, Antiurease Activities. , 2020, ss.662 - 671. 10.35378/gujs. 615818 |
| AMA | gümrükçüoğlu n,Bilgin Sökmen B Synthesis of New Ligands Containing Azomethine Group and Investigation of Antioxidant, Antiurease Activities. . 2020; 662 - 671. 10.35378/gujs. 615818 |
| Vancouver | gümrükçüoğlu n,Bilgin Sökmen B Synthesis of New Ligands Containing Azomethine Group and Investigation of Antioxidant, Antiurease Activities. . 2020; 662 - 671. 10.35378/gujs. 615818 |
| IEEE | gümrükçüoğlu n,Bilgin Sökmen B "Synthesis of New Ligands Containing Azomethine Group and Investigation of Antioxidant, Antiurease Activities." , ss.662 - 671, 2020. 10.35378/gujs. 615818 |
| ISNAD | gümrükçüoğlu, nurhan - Bilgin Sökmen, Bahar. "Synthesis of New Ligands Containing Azomethine Group and Investigation of Antioxidant, Antiurease Activities". (2020), 662-671. https://doi.org/10.35378/gujs. 615818 |
| APA | gümrükçüoğlu n, Bilgin Sökmen B (2020). Synthesis of New Ligands Containing Azomethine Group and Investigation of Antioxidant, Antiurease Activities. Gazi University Journal of Science, 33(3), 662 - 671. 10.35378/gujs. 615818 |
| Chicago | gümrükçüoğlu nurhan,Bilgin Sökmen Bahar Synthesis of New Ligands Containing Azomethine Group and Investigation of Antioxidant, Antiurease Activities. Gazi University Journal of Science 33, no.3 (2020): 662 - 671. 10.35378/gujs. 615818 |
| MLA | gümrükçüoğlu nurhan,Bilgin Sökmen Bahar Synthesis of New Ligands Containing Azomethine Group and Investigation of Antioxidant, Antiurease Activities. Gazi University Journal of Science, vol.33, no.3, 2020, ss.662 - 671. 10.35378/gujs. 615818 |
| AMA | gümrükçüoğlu n,Bilgin Sökmen B Synthesis of New Ligands Containing Azomethine Group and Investigation of Antioxidant, Antiurease Activities. Gazi University Journal of Science. 2020; 33(3): 662 - 671. 10.35378/gujs. 615818 |
| Vancouver | gümrükçüoğlu n,Bilgin Sökmen B Synthesis of New Ligands Containing Azomethine Group and Investigation of Antioxidant, Antiurease Activities. Gazi University Journal of Science. 2020; 33(3): 662 - 671. 10.35378/gujs. 615818 |
| IEEE | gümrükçüoğlu n,Bilgin Sökmen B "Synthesis of New Ligands Containing Azomethine Group and Investigation of Antioxidant, Antiurease Activities." Gazi University Journal of Science, 33, ss.662 - 671, 2020. 10.35378/gujs. 615818 |
| ISNAD | gümrükçüoğlu, nurhan - Bilgin Sökmen, Bahar. "Synthesis of New Ligands Containing Azomethine Group and Investigation of Antioxidant, Antiurease Activities". Gazi University Journal of Science 33/3 (2020), 662-671. https://doi.org/10.35378/gujs. 615818 |
