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Synthesis, characterization, anti-microbial activity studies of salicylic acid and 2-aminopyridine derivatives salts and their Cu(II) complexes

Yıl 2024, Sayı: 056, 94 - 104, 31.03.2024

Halil İlkimen Aysel Gülbandılar

https://doi.org/10.59313/jsr-a.1401073

Öz

Four salts (1-4) obtained between salicylic acid (H2salic) and 2-amino-Xpyridine {X = (2ap), 3-methyl (2a3mp), 4-methyl (2a4mp) and 5-methyl (2a5mp)} and the Cu(II) complex of H2salic (5) by methods available in the literature and new Cu(II) complexes (6-9) of the salts (1-4) has been prepared. The Cu(II) complexes (6-9) were suggested by elemental analysis, FT-IR, AAS, UV-Vis and magnetic susceptibility techniques. The spectroscopic research results indicated that complexes 6-9 have tetrahedral geometries. Additionally, antimicrobial activities of free ligands (H2salic, 2ap, 2a3mp, 2a4mp and 2a5mp), 1-9 were studied against Candida albicans (F89) yeast, Staphylococcus aureus (NRRL B-767), Pseudomonas aeruginosa (ATCC 27853), Bacillus subtilis, Listeria monocytogenes (ATCC 7644), Escherichia coli (ATCC25922) and Enterococcus faecalis (ATCC 29212) bacteria. The results were comparisoned with the control compounds (Fluconazole, Vancomycin, Cefepime and Levofloxacin). All compounds showed activity against bacteria and yeasts.

Anahtar Kelimeler

2-Aminopyridine salicylic acid salt Cu(II) complexes anti-bacterial and anti-fungal activities

Kaynakça

  • [1] Marinescu, M. (2017). “2-Aminopyridine – a classic and trendy pharmacophore”. International Journal of Pharma and Bio Sciences, vol. 8, no. 2, pp. 338-355, doi: 10.22376/ijpbs.2017.8.2.p338-355.
  • [2] Rosheen, S. S. and Utreja, D. (2023). “Salicylic acid: synthetic strategies and their biological activities”. ChemistrySelect, vol. 8, pp. e202204614, doi: 10.1002/slct.202204614.
  • [3] Rao, C. N. R., Natarajan, S. and Vaidhyanathan, R. (2004). “Metal carboxylates with open architectures”. Angewandte Chemie International Edition, vol. 43, pp. 1466-1496, doi: 10.1002/anie.200300588.
  • [4] Yin, M. C., Ai, C. C., Yuan, L. J., Wang, C. W. and Sun, J. T. (2004). “Synthesis, structure and luminescent property of a binuclear terbium complex [Tb2(Hsal)8(H2O)2][(Hphen)2].2H2O”. Journal of Molecular Structure, vol. 691, no. 1-3, pp. 33-37, doi: 10.1016/j.molstruc.2003.10.032.
  • [5] Shake, A. R., Tsai, H. L., Webb, R. J., Folting, K., Christou, G. and Hendrickson, D.N.
  • (1994). “High-spin molecules: Iron(III) incorporation into [Mn12O12(O2CMe)16(H2O)4] to yield [Mn8Fe4O12(O2CMe)16(H2O)4] and its influence on the S = 10 ground state of the former”. Inorganic Chemistry, vol. 33, no. 26, pp. 6020-6028, doi: 10.1021/ic00104a009.
  • [6] Murugavel, R., Karambelkar, V. V., Anantharaman, G. and Walawalkar, M. G. (2001). “Synthesis, spectral characterization, and structural studies of 2-aminobenzoate complexes of divalent alkaline earth metal ıons:  X-ray crystal structures of [Ca(2-aba)2(OH2)3]∞, [{Sr(2-aba)2(OH2)2}·H2O]∞, and [Ba(2-aba)2(OH2)]∞ (2-abaH = 2-NH2C6H4COOH)”. Inorganic Chemistry, vol. 39, pp. 1381-1390., doi: 10.1021/ic990895k.
  • [7] Murugavel, R., Baheti, K. and Anantharaman, G. (2001). “Reactions of 2-mercaptobenzoic acid with divalent alkaline earth metal ions: synthesis, spectral studies, and single-crystal X-ray structures of calcium, strontium, and barium complexes of 2,2'-dithiobis(benzoic acid)”. Inorganic Chemistry, vol. 40, pp. 6870-6878, doi: 10.1021/ic010519b.
  • [8] Murugavel, R., Krishnamurthy, D. and Sathiyendiran, M. (2002). “Anionic metal-organic and cationic organic layer alternation in the coordination polymers [{M(BTEC)(OH2)4}{C4H12N2}.4H2O]n (M = Co, Ni, and Zn; BTEC = 1,2,4,5-benzenetetracarboxylate)”. Journal of the Chemical Society, pp. 34-39, doi: 10.1039/B105687P.
  • [9] Murugavel, R. and Banerjee, S. (2003). “First alkaline earth metal 3-aminobenzoate (3-aba) complex: 1-D polymeric [Ca(3-aba)2(H2O)2]n assembly”. Inorganic Chemistry Communications, vol. 6, pp. 810-814, doi: 10.1016/S1387-7003(03)00112-6.
  • [10] Prabusankar, G. and Murugavel, R. (2004). “Hexameric organotincarboxylates with cyclic and drum structures”. Organometallics, vol. 23, pp. 5644-5647, doi: 10.1021/om049584u.
  • [11] Han, B. and Hoang, B.X. (2018). “Metal complexes as pharmaceuticals for treatment and prevention of cancer and inflammatory diseases”. US20180353539A1.
  • [12] Connor et al. M. O’. (2012). “Copper(II) complexes of salicylic acid combining superoxide dismutase mimetic properties with DNA binding and cleaving capabilities display promising chemotherapeutic potential with fast acting in vitro cytotoxicity against cisplatin sensitive and resista”. Journal of Medicinal Chemistry, vol. 55, pp. 1957-1968, doi: 10.1021/jm201041d.
  • [13] Ravaeva, M. Y., Cheretaev, I. V. and Chuyan, E. N. (2021). “Metal salicylates Co2+, Zn2+, Ni2+, Mn2+, Li+ and Mg2+: properties and effect on pain sensitivity”. Journal of Physics: Conference Series, vol. 1967, pp. 012033, doi: 10.1088/1742-6596/1967/1/012033.
  • [14] Diaz, A. M., Villalonga, R. and Cao, R. (2009). “Antioxidative properties of copper(II) complexes”. Journal of Coordination Chemistry, vol. 62, no. 1, pp. 100-107, doi: 10.1080/00958970802474755.
  • [15] Geraghty, M., Sheridan, V., McCann, M., Devereux, M. and McKee, V. (1999). “Synthesis and anti-Candida activity of copper(II) and manganese(II) carboxylate complexes X-ray crystal structures of [Cu(sal)(bipy)]C2H5OH.H2O and [Cu(norb)(phen)2].6.5H2O (salH2 = salicylic acid; norbH2 = cis-5-norbornene-endo-2,3-dicarboxylic acid; bipy = 2,2'-bipyridine; phen = 1,10-phenanthroline)”. Polyhedron, vol. 18, no. 22, pp. 2931-2939, doi: 10.1016/S0277-5387(99)00201-6.
  • [16] Icbudak, H. et al. (2003). “Syntheses, characterization and crystal structures of novel amine adducts of metal saccharinates, orotates and salicylates”. Journal of Molecular Structure, vol. 657, no. 1-3, pp. 255-270, doi: 10.1016/S0022-2860(03)00404-6.
  • [17] Devereux, M. et al. (2007). “Synthesis, catalase, superoxide dismutase and antitumor activities of copper(II) carboxylate complexes incorporating benzimidazole, 1,10-phenanthroline and bipyridine ligands: X-ray crystal structures of [Cu(BZA)2(bipy)(H2O)], [Cu(SalH)2(BZDH)2] and [Cu(CH3COO)2(5,6-DMBZDH)2] (SalH2 = salicylic acid; BZAH = benzoic acid; BZDH = benzimidazole and 5,6-DMBZDH = 5,6-dimethylbenzimidazole)”. Polyhedron, vol. 26, no. 15, pp. 4073-4084, doi: 10.1016/j.poly.2007.05.006.
  • [18] Han, B. and Hoang, B. X. (2018). “Metal complexes as pharmaceuticals for treatment and prevention of cancer and inflammatory diseases”. United States, US20180353539 A1 2018-12-13.
  • [19] Cluzan, R. and Nicod, B. (1971). “Analgesic and antiinflammatory effects of aminopyridine salicylates”. France, FR2085646 A5 1971-12-31.
  • [20] Sikkema, D. J. (2007). “A rigid rod polypyridobisimidazole: "M5", towards a new generation of structural composites”. 1st Proceedings of the Aachen-Dresden International Textile Conference, pp. 36-56.
  • [21] Montoro, D. F., Calatayud, D. J. and Vilar, D. A. (1979). “Salicyclic acid derivatives”. Spain, ES475267 A1 1979-05-01.
  • [22] Lu, J. F., Ge, H. G. and Min, S. T. (2011). “Syntheses and structural characterization of silver(I) complexes with pyridine and carboxylate derivatives”. Russian Journal of Coordination Chemistry, vol. 37, no. 1, pp. 36-39, doi: 10.1134/S107032841101009X.
  • [23] Hanif, M., Khan, E., Khalid, M., Tahir, M. N., Morais, S. F. A. and Braga, A. A. C. (2020). “2-Amino-3-methylpyridinium, 2-amino-4-methylbenzothiazolium and 2-amino-5-chloropyridinium salts. Experimental and theoretical findings”. Journal of Molecular Structure, vol. 1222, pp. 128914, doi: 10.1016/j.molstruc.2020.128914.
  • [24] Hemamalini, M. and Fun, H. K. (2010). “2-Amino-4-methylpyridinium 2-hydroxybenzoate”. Acta Crystallographica Section E: Crystallographic Communications, vol. E66, no. 8, pp. o2151-o2152, doi: 10.1107/S160053681002965X.
  • [25] Prabha, D., Harish, P., Babu, B. and Moorthi, V. S. N. (2016). “Growth and characterization of an organic crystal and DFT studies of 2-amino 5-methyl pyridinium salicylate”. Oriental Journal of Chemistry, vol. 32, no. 4, pp. 1937-1945, doi: 10.13005/ojc/320420.
  • [26] Punithaveni, B., Thilagavathy, K., Muthukumarasamy, N., Nithyaprakash, D. and Saravanabhavan, M. (2018). “Structural, spectral, electrical, Z-scan and HOMO LUMO studies on new 2-amino-6-methylpyridinium 2-hydroxybenzoate crystal”. Materials Science-Poland, vol. 36, no. 4, pp. 537-546, doi: 10.2478/msp-2018-0098.
  • [27] Sivakumar, P., Sudhahar, S., Israel S. and Chakkaravarthi, G. (2016). “2-Amino-6-methylpyridinium 2-hydroxybenzoate”. IUCrData, vol. 1, no. 5, pp. x160747-x60750, doi: 10.1107/S2414314616007471.
  • [28] İlkimen, H. and Yenikaya, C. (2017). “Synthesis and characterization of mixed ligand Cu(II) complexes of salicylic acid derivatives with 2-aminobenzotiyazol derivatives”. Pamukkale University Journal of Engineering Sciences, vol. 23, no. 7, pp. 899-907, doi: 10.5505/pajes.2016.76735.
  • [29] Nakamoto, K. (1997). “Infrared and raman spectra of inorganic and coordination compounds”. 5th ed. NewYork: Wiley-Interscience, pp. 232.
  • [30] Büyükkıdan N. and Ozer, S. (2013). “Synthesis and characterization of Ni(II) and Cu(II) complexes derived from novel phenolic Mannich bases”. Turkish Journal of Chemistry, vol. 37, no. 1, pp. 101-110, doi: 10.3906/kim-1203-67.
  • [31] Hathaway, B. J., Holah, D. G. and Underhill, A. E. (1962). “468. The preparation and properties of some bivalent transition-metal tetrafluoroborate–methyl cyanide complexes”. Journal of the Chemical Society, vol. 24, no. 4, pp. 2444-2448, 1962, doi: 10.1039/JR9620002444.
  • [32] Rehman, S. U., Ikram, M., Rehman, S., Islam, N. U., Jan, N. and Mex, J. (2011). “Synthesis and characterization of Ni(II), Cu(II) and Zn(II) tetrahedral transition metal complexes of modified hydrazine”. Revista de la Sociedad Química de Mexico, vol. 55, no. 3, pp. 164-167, doi: 10.29356/jmcs.v55i3.815.
  • [33] Yenikaya, C. et al. (2011). “Synthesis, characterization and biological evaluation of novel Cu(II) complexes with proton transfer salt of 2,6-pyridinedicarboxylic acid and 2-amino-4-methylpyridine”. Journal of Coordination Chemistry, vol. 64, no. 19, pp. 3353-3365, doi: 10.1080/00958972.2011.620608.
  • [34] İlkimen, H., Türken, N. and Gülbandılar, A. (2021). “Synthesis, characterization, antimicrobial and antifungal activity of studies of two novel aminopyridine-sulfamoylbenzoic acid salts and their Cu(II) complexes”. Journal of the Iranian Chemical Society, vol. 18, pp. 1941–1946, doi: 10.1007/s13738-021-02157-4.
  • [35] İlkimen, H., Salün, S. G., Gülbandılar, A. and Sarı, M. (2022). “The new salt of 2-amino-3-methylpyridine with dipicolinic acid and its metal complexes: Synthesis, characterization and antimicrobial activity studies”. Journal of Molecular Structure, vol. 1270, pp. 133961, doi: 10.1016/j.molstruc.2022.133961.
  • [36] İlkimen H. and Gülbandılar A. (2023). “Synthesis, characterization, antimicrobial and antifungal activity studies of four novel 2-aminopyridine and 2,4-dichloro-5-sulfamoylbenzoic acid salts and their Cu(II) complexes”. Kuwait Journal of Science, vol. 50, no. 3A, pp. 1-11, doi: 10.48129/kjs.19163.

Yıl 2024, Sayı: 056, 94 - 104, 31.03.2024

Halil İlkimen Aysel Gülbandılar

https://doi.org/10.59313/jsr-a.1401073

Öz

Kaynakça

  • [1] Marinescu, M. (2017). “2-Aminopyridine – a classic and trendy pharmacophore”. International Journal of Pharma and Bio Sciences, vol. 8, no. 2, pp. 338-355, doi: 10.22376/ijpbs.2017.8.2.p338-355.
  • [2] Rosheen, S. S. and Utreja, D. (2023). “Salicylic acid: synthetic strategies and their biological activities”. ChemistrySelect, vol. 8, pp. e202204614, doi: 10.1002/slct.202204614.
  • [3] Rao, C. N. R., Natarajan, S. and Vaidhyanathan, R. (2004). “Metal carboxylates with open architectures”. Angewandte Chemie International Edition, vol. 43, pp. 1466-1496, doi: 10.1002/anie.200300588.
  • [4] Yin, M. C., Ai, C. C., Yuan, L. J., Wang, C. W. and Sun, J. T. (2004). “Synthesis, structure and luminescent property of a binuclear terbium complex [Tb2(Hsal)8(H2O)2][(Hphen)2].2H2O”. Journal of Molecular Structure, vol. 691, no. 1-3, pp. 33-37, doi: 10.1016/j.molstruc.2003.10.032.
  • [5] Shake, A. R., Tsai, H. L., Webb, R. J., Folting, K., Christou, G. and Hendrickson, D.N.
  • (1994). “High-spin molecules: Iron(III) incorporation into [Mn12O12(O2CMe)16(H2O)4] to yield [Mn8Fe4O12(O2CMe)16(H2O)4] and its influence on the S = 10 ground state of the former”. Inorganic Chemistry, vol. 33, no. 26, pp. 6020-6028, doi: 10.1021/ic00104a009.
  • [6] Murugavel, R., Karambelkar, V. V., Anantharaman, G. and Walawalkar, M. G. (2001). “Synthesis, spectral characterization, and structural studies of 2-aminobenzoate complexes of divalent alkaline earth metal ıons:  X-ray crystal structures of [Ca(2-aba)2(OH2)3]∞, [{Sr(2-aba)2(OH2)2}·H2O]∞, and [Ba(2-aba)2(OH2)]∞ (2-abaH = 2-NH2C6H4COOH)”. Inorganic Chemistry, vol. 39, pp. 1381-1390., doi: 10.1021/ic990895k.
  • [7] Murugavel, R., Baheti, K. and Anantharaman, G. (2001). “Reactions of 2-mercaptobenzoic acid with divalent alkaline earth metal ions: synthesis, spectral studies, and single-crystal X-ray structures of calcium, strontium, and barium complexes of 2,2'-dithiobis(benzoic acid)”. Inorganic Chemistry, vol. 40, pp. 6870-6878, doi: 10.1021/ic010519b.
  • [8] Murugavel, R., Krishnamurthy, D. and Sathiyendiran, M. (2002). “Anionic metal-organic and cationic organic layer alternation in the coordination polymers [{M(BTEC)(OH2)4}{C4H12N2}.4H2O]n (M = Co, Ni, and Zn; BTEC = 1,2,4,5-benzenetetracarboxylate)”. Journal of the Chemical Society, pp. 34-39, doi: 10.1039/B105687P.
  • [9] Murugavel, R. and Banerjee, S. (2003). “First alkaline earth metal 3-aminobenzoate (3-aba) complex: 1-D polymeric [Ca(3-aba)2(H2O)2]n assembly”. Inorganic Chemistry Communications, vol. 6, pp. 810-814, doi: 10.1016/S1387-7003(03)00112-6.
  • [10] Prabusankar, G. and Murugavel, R. (2004). “Hexameric organotincarboxylates with cyclic and drum structures”. Organometallics, vol. 23, pp. 5644-5647, doi: 10.1021/om049584u.
  • [11] Han, B. and Hoang, B.X. (2018). “Metal complexes as pharmaceuticals for treatment and prevention of cancer and inflammatory diseases”. US20180353539A1.
  • [12] Connor et al. M. O’. (2012). “Copper(II) complexes of salicylic acid combining superoxide dismutase mimetic properties with DNA binding and cleaving capabilities display promising chemotherapeutic potential with fast acting in vitro cytotoxicity against cisplatin sensitive and resista”. Journal of Medicinal Chemistry, vol. 55, pp. 1957-1968, doi: 10.1021/jm201041d.
  • [13] Ravaeva, M. Y., Cheretaev, I. V. and Chuyan, E. N. (2021). “Metal salicylates Co2+, Zn2+, Ni2+, Mn2+, Li+ and Mg2+: properties and effect on pain sensitivity”. Journal of Physics: Conference Series, vol. 1967, pp. 012033, doi: 10.1088/1742-6596/1967/1/012033.
  • [14] Diaz, A. M., Villalonga, R. and Cao, R. (2009). “Antioxidative properties of copper(II) complexes”. Journal of Coordination Chemistry, vol. 62, no. 1, pp. 100-107, doi: 10.1080/00958970802474755.
  • [15] Geraghty, M., Sheridan, V., McCann, M., Devereux, M. and McKee, V. (1999). “Synthesis and anti-Candida activity of copper(II) and manganese(II) carboxylate complexes X-ray crystal structures of [Cu(sal)(bipy)]C2H5OH.H2O and [Cu(norb)(phen)2].6.5H2O (salH2 = salicylic acid; norbH2 = cis-5-norbornene-endo-2,3-dicarboxylic acid; bipy = 2,2'-bipyridine; phen = 1,10-phenanthroline)”. Polyhedron, vol. 18, no. 22, pp. 2931-2939, doi: 10.1016/S0277-5387(99)00201-6.
  • [16] Icbudak, H. et al. (2003). “Syntheses, characterization and crystal structures of novel amine adducts of metal saccharinates, orotates and salicylates”. Journal of Molecular Structure, vol. 657, no. 1-3, pp. 255-270, doi: 10.1016/S0022-2860(03)00404-6.
  • [17] Devereux, M. et al. (2007). “Synthesis, catalase, superoxide dismutase and antitumor activities of copper(II) carboxylate complexes incorporating benzimidazole, 1,10-phenanthroline and bipyridine ligands: X-ray crystal structures of [Cu(BZA)2(bipy)(H2O)], [Cu(SalH)2(BZDH)2] and [Cu(CH3COO)2(5,6-DMBZDH)2] (SalH2 = salicylic acid; BZAH = benzoic acid; BZDH = benzimidazole and 5,6-DMBZDH = 5,6-dimethylbenzimidazole)”. Polyhedron, vol. 26, no. 15, pp. 4073-4084, doi: 10.1016/j.poly.2007.05.006.
  • [18] Han, B. and Hoang, B. X. (2018). “Metal complexes as pharmaceuticals for treatment and prevention of cancer and inflammatory diseases”. United States, US20180353539 A1 2018-12-13.
  • [19] Cluzan, R. and Nicod, B. (1971). “Analgesic and antiinflammatory effects of aminopyridine salicylates”. France, FR2085646 A5 1971-12-31.
  • [20] Sikkema, D. J. (2007). “A rigid rod polypyridobisimidazole: "M5", towards a new generation of structural composites”. 1st Proceedings of the Aachen-Dresden International Textile Conference, pp. 36-56.
  • [21] Montoro, D. F., Calatayud, D. J. and Vilar, D. A. (1979). “Salicyclic acid derivatives”. Spain, ES475267 A1 1979-05-01.
  • [22] Lu, J. F., Ge, H. G. and Min, S. T. (2011). “Syntheses and structural characterization of silver(I) complexes with pyridine and carboxylate derivatives”. Russian Journal of Coordination Chemistry, vol. 37, no. 1, pp. 36-39, doi: 10.1134/S107032841101009X.
  • [23] Hanif, M., Khan, E., Khalid, M., Tahir, M. N., Morais, S. F. A. and Braga, A. A. C. (2020). “2-Amino-3-methylpyridinium, 2-amino-4-methylbenzothiazolium and 2-amino-5-chloropyridinium salts. Experimental and theoretical findings”. Journal of Molecular Structure, vol. 1222, pp. 128914, doi: 10.1016/j.molstruc.2020.128914.
  • [24] Hemamalini, M. and Fun, H. K. (2010). “2-Amino-4-methylpyridinium 2-hydroxybenzoate”. Acta Crystallographica Section E: Crystallographic Communications, vol. E66, no. 8, pp. o2151-o2152, doi: 10.1107/S160053681002965X.
  • [25] Prabha, D., Harish, P., Babu, B. and Moorthi, V. S. N. (2016). “Growth and characterization of an organic crystal and DFT studies of 2-amino 5-methyl pyridinium salicylate”. Oriental Journal of Chemistry, vol. 32, no. 4, pp. 1937-1945, doi: 10.13005/ojc/320420.
  • [26] Punithaveni, B., Thilagavathy, K., Muthukumarasamy, N., Nithyaprakash, D. and Saravanabhavan, M. (2018). “Structural, spectral, electrical, Z-scan and HOMO LUMO studies on new 2-amino-6-methylpyridinium 2-hydroxybenzoate crystal”. Materials Science-Poland, vol. 36, no. 4, pp. 537-546, doi: 10.2478/msp-2018-0098.
  • [27] Sivakumar, P., Sudhahar, S., Israel S. and Chakkaravarthi, G. (2016). “2-Amino-6-methylpyridinium 2-hydroxybenzoate”. IUCrData, vol. 1, no. 5, pp. x160747-x60750, doi: 10.1107/S2414314616007471.
  • [28] İlkimen, H. and Yenikaya, C. (2017). “Synthesis and characterization of mixed ligand Cu(II) complexes of salicylic acid derivatives with 2-aminobenzotiyazol derivatives”. Pamukkale University Journal of Engineering Sciences, vol. 23, no. 7, pp. 899-907, doi: 10.5505/pajes.2016.76735.
  • [29] Nakamoto, K. (1997). “Infrared and raman spectra of inorganic and coordination compounds”. 5th ed. NewYork: Wiley-Interscience, pp. 232.
  • [30] Büyükkıdan N. and Ozer, S. (2013). “Synthesis and characterization of Ni(II) and Cu(II) complexes derived from novel phenolic Mannich bases”. Turkish Journal of Chemistry, vol. 37, no. 1, pp. 101-110, doi: 10.3906/kim-1203-67.
  • [31] Hathaway, B. J., Holah, D. G. and Underhill, A. E. (1962). “468. The preparation and properties of some bivalent transition-metal tetrafluoroborate–methyl cyanide complexes”. Journal of the Chemical Society, vol. 24, no. 4, pp. 2444-2448, 1962, doi: 10.1039/JR9620002444.
  • [32] Rehman, S. U., Ikram, M., Rehman, S., Islam, N. U., Jan, N. and Mex, J. (2011). “Synthesis and characterization of Ni(II), Cu(II) and Zn(II) tetrahedral transition metal complexes of modified hydrazine”. Revista de la Sociedad Química de Mexico, vol. 55, no. 3, pp. 164-167, doi: 10.29356/jmcs.v55i3.815.
  • [33] Yenikaya, C. et al. (2011). “Synthesis, characterization and biological evaluation of novel Cu(II) complexes with proton transfer salt of 2,6-pyridinedicarboxylic acid and 2-amino-4-methylpyridine”. Journal of Coordination Chemistry, vol. 64, no. 19, pp. 3353-3365, doi: 10.1080/00958972.2011.620608.
  • [34] İlkimen, H., Türken, N. and Gülbandılar, A. (2021). “Synthesis, characterization, antimicrobial and antifungal activity of studies of two novel aminopyridine-sulfamoylbenzoic acid salts and their Cu(II) complexes”. Journal of the Iranian Chemical Society, vol. 18, pp. 1941–1946, doi: 10.1007/s13738-021-02157-4.
  • [35] İlkimen, H., Salün, S. G., Gülbandılar, A. and Sarı, M. (2022). “The new salt of 2-amino-3-methylpyridine with dipicolinic acid and its metal complexes: Synthesis, characterization and antimicrobial activity studies”. Journal of Molecular Structure, vol. 1270, pp. 133961, doi: 10.1016/j.molstruc.2022.133961.
  • [36] İlkimen H. and Gülbandılar A. (2023). “Synthesis, characterization, antimicrobial and antifungal activity studies of four novel 2-aminopyridine and 2,4-dichloro-5-sulfamoylbenzoic acid salts and their Cu(II) complexes”. Kuwait Journal of Science, vol. 50, no. 3A, pp. 1-11, doi: 10.48129/kjs.19163.
Toplam 37 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Biyoinorganik Kimya, Geçiş Metal Kimyası
Bölüm Research Articles
Yazarlar

Halil İlkimen 0000-0003-1747-159X

Aysel Gülbandılar 0000-0001-9075-9923

Yayımlanma Tarihi 31 Mart 2024
Gönderilme Tarihi 6 Aralık 2023
Kabul Tarihi 20 Mart 2024
Yayımlandığı Sayı Yıl 2024 Sayı: 056

Kaynak Göster

IEEE H. İlkimen ve A. Gülbandılar, “Synthesis, characterization, anti-microbial activity studies of salicylic acid and 2-aminopyridine derivatives salts and their Cu(II) complexes”, JSR-A, sy. 056, ss. 94–104, Mart 2024, doi: 10.59313/jsr-a.1401073.
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