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2,6-Piridindikarboksilik Asit ile 2-Amino-4,6-dimetilpiridinin Tuzu ve Metal Komplekslerinin Sentezi, Karakterizasyonu ve Antimikrobiyal Özelliklerinin İncelenmesi

Year 2024, Volume: 8 Issue: 2, 115 - 130, 30.12.2024
https://doi.org/10.47137/usufedbid.1480103

Abstract

2,6-Piridindikarboksilik asit (1) ile 2-amino-4,6-dimetilpiridinin (2) yeni tuz (3) ve tuzun metal kompleksleri {(H2)x[M(1)2].nH2O, M = Fe (III), x = 1, n = 3 (4); M = Co(II), x = 2, n = 4 (5); M = Ni(II), x = 2, n = 5 (6); M = Cu(II), x = 2, n = 4 (7)} sentezlenmiştir. Bileşiklerin yapıları, AAS, IR, UV, manyetik duyarlılık ve molar iletkenlik metotları ile önerilmiştir. Spektroskopik analizler sonucunda tüm metal komplekslerinin iyonik ve oktahedral yapıya sahip olduğu gözlenmiştir Tüm maddelerin Candida albicans (ATCC 14053) mayasına, Listeria monocytogenes (ATCC 7644), Staphylococcus aureus (NRRL-B 767), Bacillus subtilis, Enterococcus faecalis (ATCC 29212), Pseudomonas aeruginosa (ATCC 27853), ve Escherichia coli (ATCC 25922) bakterilerine karşı antimikrobiyal aktiviteleri incelenmiştir. Antimikrobiyal aktivite sonuçları Flukonazol, Ketokonazol, Kloramfenikol, Levofloksasin, Vankomisin ve Sefepim ile kıyaslanmıştır. Aktivite sonuçlarında en iyi değerler B. subtilis bakterisinde 3, S. aureus bakterilerinde 6 ve 7, P. aeruginosa bakterisinde 5-7, L. monocytogenes bakterisinde tüm bileşikler, E. coli bakterisinde tüm bileşikler (2 hariç), E. faecalis bakterisinde 2 ve C. albicans mayasında 4 gözlenmiştir.

Thanks

This study was supported within the scope of the TUBITAK 2209-A university students’ research projects support program with the application number 1919B012107912.

References

  • Braga D, Grepioni F, Novoa JJ, Inter-anion O–H–··· O–hydrogen bond like interactions: the breakdown of the strength–length analogy. Chemical Communication, 1998;18:1959–1960.
  • Desiraju GR, A bond by any other name. Angewandte Chemie, 2011;50:52–59.
  • Aghabozorg H, Mantegh F, Sheshmani S, A brief review on structural concepts of novel supramolecular proton transfer compounds and their metal complexes. Journal of the Iranian Chemical Society, 2008;5(2):184-227.
  • Refat MS, Adam AMA, Saad HA, Utility of charge-transfer complexation for the assessment of macrocyclic polyethers: Spectroscopic, thermal and surface morphology characteristics of two highly crown ethers complexed with acido acceptors. Journal of Molecular Structure, 2015;1085:178–190.
  • Gopi R, Ramanathan N, Sundararajan K, Hydrogen-bonded complexes of acetylene and acetonitrile: A matrix isolation infrared and computational study. Journal of Molecular Structure, 2015;1083:364–373.
  • Al-Ahmary KM, Habeeb M, Al-Solmy EA, Spectroscopic studies of the hydrogen bonded charge transfer complex of 2-aminopyridine with π-acceptor chloranilic acid in different polar solvents, Journal of Molecular Liquids, 2011;162:129–134.
  • Alexeev YE, Kharisov BI, Hermandez TC, Garnovski AD, Coordination motifs in modern supramolecular chemistry. Coordination Chemistry Review, 2010;254:794–831.
  • Celestine MJ, Bullock JL, Boodram S, Rambaran VH, Holder AA, Interesting properties of p-, d-, and f-block elements when coordinated with dipicolinic acid and its derivatives as ligands: their use as inorganic pharmaceuticals. Reviews in Inorganic Chemistr, 2015;35(2):57-67.
  • Kirillov AM, Shul’pin GB, Pyrazinecarboxylic acid and analogs: highly efficient co-catalysts in the metal-complex-catalyzed oxidation of organic compounds. Coordination Chemistry Reviews, 2013;257:732-754.
  • Kirillova MV, Guedes da Silva MFC, Kirillov AM, Frausto da Silva JJR, Pombeiro AJL, 3D hydrogen bonded heteronuclear CoII, NiII, CuII and ZnII aqua complexes derived from dipicolinic acid. Inorganica Chimica Acta, 2007;360:506-512.
  • Marinescu M, 2-Aminopyridine – a classic and trendy pharmacophore. International Journal of Pharma and Bio Sciences, 2017;8(2):338-335.
  • Yenikaya C, Poyraz M, Sarı M, Demirci F, İlkimen H, Büyükgüngör O, Synthesis, characterization and biological evaluation of a novel Cu(II) complex with the mixed ligands 2,6-pyridinedicarboxylicacid and 2-aminopyridine. Polyhedron, 2009;28(16):3526-3532.
  • Yenikaya C, Büyükkıdan N, Sarı M, Keşli R, İlkimen H, Bülbül M, Büyükgüngör O, 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, 2011;64(19):3353-3365.
  • Hakimi M, Motieiyan E, Bertolotti F, Marabello D, Nunes R, Vitor H, Three new bismuth(III) pyridine-2,6-dicarboxylate compounds: Synthesis, characterization and crystalstructures. Journal of Molecular Structure, 2015;1099:523-533.
  • Sharma G, Narula AK, Synthesis and optoelectronic properties of three Eu(III)-dipicolinate complexes based on a-picolinic acid, 2-aminopyridine and 2-hydroxypyridine as secondary ligands. Journal of Materials Science: Materials in Electronics, 2015;26(2):1009-1017.
  • Mirzaei M, Eshtiagh-Hosseini H, Karrabi Z, Molcanov K, Eydizadeh E, Mague JT, Bauza A, Frontera A, Crystal engineering with coordination compounds of NiII, CoII, and CrIII bearing dipicolinic acid driven by the nature of the noncovalent interactions. CrystEngComm, 2014;16(24):5352-5363.
  • Sheshmani S, Ghadermazi M, Motieiyan E, Shokrollahi A, Malekhosseini Z, Fashapoyeh MA, Potentiometric and structural studies of MIIA(Ca, Sr, Ba)-pyridine-2,6-dicarboxylic acid-2-aminopyridine adduct. Journal of Coordination Chemistry, 2013;66(22):3949-3969.
  • Mistri S, Zangrando E, Manna SC, Cu(II) complexes of pyridine-2,6-dicarboxylate and N-donor neutral ligands: Synthesis, crystal structure, thermal behavior, DFT calculation and effect of aromatic compounds on their fluorescence. Inorganica Chimica Acta, 2013;405:331-338.
  • Mirzaei M, Eshtiagh-Hosseini H, Mague JT, 2-Aminopyridinium bis(pyridine-2,6-dicarboxylato)ferrate(III). Acta Crystallographica, Section E: Structure Reports Online, 2012;68(2):m174-m174.
  • Trivedi M, Nagarajan R, Kumar A, Rath NP, A new single pot synthesis of m-bis(oxido)bis{oxidovanadium(V)} dipicolinato complex with 2-aminopyridinium as counter cation: Spectroscopic, structural, catalytic and theoretical studies. Journal of Organometallic Chemistry, 2010;695(12-13):1722-1728.
  • Pramanik S, Konar S, Chakraborty K, Pal T, Das S, Chatterjee S, Dolai M, Pathak S, Investigation of electrical conductance properties, non-covalent interactions and TDDFT calculation of a newly synthesized copper(II) metal complex. Journal of Molecular Structure, 2020;1206:127663.
  • Zohrevandi M, Abdolmaleki S, Ghadermazi M, Gholiee Y, Aliabadi A, Motieiyan E, Hakimi M, Marabello D, Synthesis, characterization, crystallographic structure, theoretical studies, and in vitro cytotoxicity assessment of two Gd(III) and Ce(IV) complexes containing pyridine-2,6-dicarboxylate. Polyhedron, 2022;211:115561.
  • Foroughian M, Foroumadi A, Notash B, Bruno G, Rudbari AH, Aghabozorg H, 2,3-Diaminopyridinium 6-carboxypyridine-2-carboxylate. Acta Crystallographica, Section E: Structure Reports Online, 2011;67(12):o3325-o3325.
  • Aghabozorg H, Kazemi S, Agah AA, Mirzaei M, Notash B, Bis(2,3-diaminopyridinium)bis(m-pyridine-2,6-dicarboxylato)-κ4O2,N,O6:O6,κ4O2:O2,N,O6-bis[aqua(pyridine-2,6-dicarboxylato-κ3O2,N,O6)bismuthate(III)] tetrahydrate. Acta Crystallographica, Section E: Structure Reports Online, 2011;67(3):m360-m361.
  • Moghimi A, Ranjbar M, Aghabozorg H, Jalali F, Shamsipur M, Yap GPA, Rahbarnoohi H, A novel pyridine containing self-assembling system: synthesis, characterization, X-ray crystal structure, 13C solid phase NMR and solution studies. Journal of Molecular Structure, 2002;605(2-3):133-149.
  • Aghabozorg H, Saei AA, Ramezanipour F, 2,6-Diaminopyridinium pyridinium-2,6-dicarboxylate: a redetermination. Acta Crystallographica, Section E: Structure Reports Online, 2005;61(10):o3242-o3244.
  • Jamei MR, Ranjbar M, Eliassi A, Sonochemical synthesis of vanadium complex nano-particles: a new precursor for preparation and evaluation of V2O5/Al2O3 nano-catalyst in selective oxidation of methanol to methylal. Journal of the Iranian Chemical Society, 2017;14(12):2627-2635.
  • Cai M, Gao X, Chen J, Structural refinement and luminescent property of a novel europium(III) complex with a proton transfer compound containing 2,6-pyridinedicarboxylate and 2,6-pyridinediammonium ligands synthesized by ultrasonic method. Journal of Molecular Structure, 2015;1086:93-98.
  • Chen J, Gao X, Cai M, Hydrogen bond-type europium complex fluorescent material with high fluorescence intensity and good thermal stability, and preparation method thereof. Faming Zhuanli Shenqing, CN 103694266 A 20140402, 2014.
  • Tabatabaee M, Tahriri M, Tahriri M, Dusek M, Fejfarova K, Bis(2,6-diaminopyridinium) bis(pyridine-2,6-dicarboxylato)zincate(II) monohydrate. Acta Crystallographica, Section E: Structure Reports Online, 2011;67(6):m769-m770.
  • Cai M, Chen J, Wu Q, Ma X, Yang J, Li F, Preparation of hydrogen bond-type rare earth metal complex as antibacterial agents. Faming Zhuanli Shenqing, CN 101456875 A 20090617, 2009.
  • Aghabozorg H, Saei AA, Moghimi A, Ramezanipour F, Synthesis and crystal structure of a novel six-coordinate gallium(III) complex Majallah-i Bulurshinasi va Kanishinasi-i Iran, 2005;13(1):185-194.
  • Aghabozorg H, Saei AA, Sadr-Khanlou E, Moghimi A, Crystal structure of 2,6-diaminopyridinium bis(2,6-pyridinedicarboxylato)antimonate(III) trihydrate hemichloroform. X-Ray Structure Analysis Online, 2005;21(11):x207-x208.
  • Rafizadeh M, Amani V, Dihydronium bis(2,6-diaminopyridinium) tris(pyridine-2,6-dicarboxylato-κ3O,O',N)dysprosate(III) dihydrate. Acta Crystallographica, Section E: Structure Reports Online, 2006;62(1):m90-m91.
  • Aghabozorg H, Ramezanipour F, Kheirollahi PD, Saei AA, Shokrollahi A, Shamsipur M, Manteghi F, Soleimannejad J, Sharif MA, Novel complexes of gallium(III), indium(III), and thallium(III) with pyridine-containing proton transfer ion pairs obtained from dipicolinic acid - synthesis, characterization and x-ray crystal structure. Zeitschrift fuer Anorganische und Allgemeine Chemie, 2006;632(1):147-154.
  • Ssheshmani S, Kheirollahi D, Aghabozorg H, Shokrollahi A, Kickelbick G, Shamsipur M, Ramezanipour F, Moghimi A, Synthesis and crystal structure of CeIII and BiIII complexes and solution studies of ZnII, CdII, PbII, CeIII, and BiIII complexes obtained from proton transfer compounds containing 2,6-pyridinedicarboxylate ion. Zeitschrift fuer Anorganische und Allgemeine Chemie, 2005;631(15):3058-3065.
  • Rafizadeh M, Ranjbar M, Amani V, Crystal structure of gadolinium(III) complex, dihydronium (2,6-pyridinediamonium) tris-(2,6-pyridinedicarboxylato)gadolinate(III) dihydrate, C31H34GdN9O16. Analytical Sciences: X-ray Structure Analysis Online, 2005;21(7):x113-x114.
  • Aghabozorg H, Moghimi A, Manteghi F, Ranjbar M, A nine-coordinated ZrIV complex and a self-assembling system obtained from a proton transfer compound containing 2,6-pyridinedicarboxylate and 2,6-pyridinediammonium, synthesis and x-ray crystal structure. Zeitschrift fuer Anorganische und Allgemeine Chemie, 2005;631(5):909-913.
  • Ranjbar M, Aghbozorg H, Crystal structure of a polymeric Hg(II) complex of a pyridine containing a self-assembly system. Analytical Sciences: X-ray Structure Analysis Online, 2004;20(4):x153-x154.
  • Ranjbar M, Crystal structure of a five-coordinate vanadium(V) complex, 2,6-diaminopyridinum 2,6-pyridinedicarboxylatodioxovanadate(V) Analytical Sciences: X-ray Structure Analysis Online, 2004;20(July-Sept):x135-x136.
  • Ghamari S, Ranjbar M, Preparation, characterization, and the study of the electrochemical behavior of Y-doped Bariumcerate powders by new precursors. Hydrogen, Fuel Cell & Energy Storage, 2023;10:1-10.
  • Ranjbar M, Abdollahi M, Rafizadeh M, Crystal structure of a seven-coordinate thallium(III) complex, 2,6-diaminopyridinumbis(2,6-pyridinedicarboxylato)aquathallate(III)tetrahydrate Analytical Sciences: X-ray Structure Analysis Online, 2004;20(July-Sept):x133-x134.
  • Moghimi A, Shokrollahi A, Shamsipur M, Aghabozorg H, Ranjbar M, X-ray crystal structure and solution studies of hexacoordinated mercury (II) complex of a pyridine containing proton transfer compound. Journal of Molecular Structure, 2004;701(1-3):49-56.
  • Rafizadeh M, Ranjbar M, Amani V, Dihydronium 2,6-diaminopyridinium tris(2,6-pyridinedicarboxylato)ytterbate(III) dihydrate. Acta Crystallographica, Section E: Structure Reports Online, 2004;60(4):m479-m481.
  • Ranjbar M, Aghabozorg H, Moghimi A, Crystal structure of bis(2,6-diaminopyridinium) diaqua-bis-m-(2,6-pyridinedicarboxylato)-bis(2,6-pyridinedicarboxylato)dibismuthate(III) tetrahydrate, (C28H16O18N4Bi2)(C5H8N3)2.4H2O. Zeitschrift fuer Kristallographie - New Crystal Structures, 2003;218(4):432-434.
  • Moghimi A, Ranjbar M, Aghabozorg H, Jalali F, Shamsipur M, Chadha KK, Synthesis, characterization, and X-ray crystal structures of Co(II) and La(III) complexes of a pyridine containing self-assembling system and solution studies of the Co(II) complex. Canadian Journal of Chemistry, 2002;80(12):1687-1696.
  • Moghimi A, Ranjbar M, Aghabozorg H, Jalali F, Shamsipur M, Chadah RK, Synthesis, NMR characterization, x-ray crystal structure and solution studies of Ni(II) complexes of a pyridine containing self-assembling system. Journal of Chemical Research, Synopses, 2002;(10):477-479, 1047-1065.
  • Ranjbar M, Moghimi A, Aghabozorg H, Yap GPA, Crystal structure of zinc(II) complex of a pyridine containing self-assembling system. Analytical Sciences, 2002;18(2):219-220.
  • Ranjbar M, Aghabozorg H, Moghimi A, Yanovsky A, Crystal structure of 2,6-diaminopyridinium bis(2,6-pyridinedicarboxylato)chromium(III) 2,6-pyridinedicarboxylic acid hemihydrate, C26H18CrN6O12.0.5H2O. Zeitschrift fuer Kristallographie - New Crystal Structures, 2001;216(4):626-628.
  • Hejrani-Dalir A, Tabatabaee M, Sheibani A, Synthesis and crystal structure of 2-amino-3-hydroxypyridinium dioxido(pyridine-2,6-dicarboxylato-κ3O2,N,O6)vanadate(V) and its conversion to nanostructured V2O5. Acta Crystallographica, Section C: Structural Chemistry, 2015;71(2):89-92.
  • İlkimen H, Salün SG, Gülbandılar A, Sarı M, 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, 2022;1270:133961.
  • Sharif MA, Tabatabaee M, Adinehloo M, Aghabozorg H, 2-Amino-4-methylpyridinium 6-carboxypyridine-2-carboxylate sesquihydrate. Acta Crystallographica, Section E: Structure Reports Online, 2010;66(12):o3232-o3232.
  • Aghabozorg H, Rouchi AM, Mirzaei M, Notash B, 2-Amino-4-methylpyridinium 6-carboxypyridine-2-carboxylate methanol monosolvate. Acta Crystallographica, Section E: Structure Reports Online, 2011;67(1):o54-o54.
  • Cai M, Chen J, A new ultrasonic synthetic method for proton transfer compound of 2,6-pyridinedicarboxylic acid and 2,6-pyridinediamine. Youji Huaxue, 2010;30(7):1076-1079.
  • Aghabozorg H, Rouchi MA, Notash B, Mirzaei M, Bis(2-amino-4-methylpyridinium) bis(pyridine-2,6-dicarboxylato)cuprate(II) Acta Crystallographica, Section E: Structure Reports Online, 2011;67(2):m189-m189.
  • Mirzaei M, Eshtiagh-Hosseini H, Alfi N, Aghabozorg H, Gharamaleki JA, Beyramabadi SA, Khavasi HR, Salimi AR, Shokrollahi A, Aghaei R, Karami E, Syntheses, crystal, molecular structures, and solution studies of Cu(II), Co(II), and Zn(II) coordination compounds containing pyridine-2,6-dicarboxylic acid and 1,4-pyrazine-2,3-dicarboxylic acid: comparative computational studies of Cu(II) and Zn(II) complexes. Structural Chemistry, 2011;22(6):1365-1377.
  • Eshtiagh-Hosseini H, Aghabozorg H, Mirzaei M, Amini MM, Chen YG, Shokrollahi A, Aghaei R, Diversity in coordination behavior of dipicolinic acid with lead(II), calcium(II), and nickel(II) in the presence of pyrazine and 2-amino-4-methylpyridine spacers in construction of three supramolecular architectures. Journal of Molecular Structure, 2010;973(1-3):180-189.
  • Movahedi E, Razmazma H, Rezvani A, Nowroozi A, Ebrahimi A, Eigner V, Dusek M, Arjmand F, A novel Cu(II)-based DNA-intercalating agent: Structural and biological insights using biophysical and in silico techniques. Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy, 2023;293:122438.
  • Mirzaei M, Eshtiagh-Hosseini H, Karrabi Z, Notash B, Bauza A, Frontera A, Synthesis, structure and DFT study of a chelidamic acid based Cu coordination polymer: On the importance of π-π interactions and hexameric water clusters. Journal of Molecular Structure, 2015;1080:30-36.
  • Pasdar H, Ebdam A, Aghabozorg H, Notash B, Bis(2-amino-6-methylpyridinium) tris(pyridine-2,6-dicarboxylato)zirconate(IV) dihydrate. Acta Crystallographica, Section E: Structure Reports Online, 2011;67(3):m294, Sm294/1-Sm294/11.
  • Eshtiagh-Hosseini H, Yousefi Z, Shafiee M, Mirzaei M, Fe(III) and cobalt(II) coordination compounds of 5-bromo-6-methyl-2-morpholinepyrimidinium-4-amine pyridine-2,6-dicarboxylate, Journal of Coordination Chemistry, 2010;63(18):3187-3197.
  • Cook D, Vibrational spectra of yridinium salts Canadian Journal of Chemistry, 1961;39(10):2009-2024.
  • Nakamoto K, Infrared and raman spectra of inorganic and coordination compounds 5th ed NewYork: Wiley-Interscience, pp 232, 1997.
  • Geary WJ, The use of conductivity measurements in organic solvents for the characterisation of coordination compounds, Coordination Chemistry Reviews, 1971;7(1):81-122.
  • İlkimen H, Gülbandılar A, Synthesis, characterization, anti-microbial activity studies of 2-methoxy-5-sulfamoylbenzoic acid and 2-aminopyridine derivatives salts and their Cu(II) complexes. Pamukkale University Journal of Engineering Sciences, 2024; Doi. 10.5505/pajes.2024.48196.
  • İlkimen H, Gülbandılar A, Synthesis, characterization, anti-microbial activity studies of salicylic acid and 2-aminopyridine derivatives salts and their Cu(II) complexes. Journal of Scientific Reports-A, 2024;56:94-104.

Synthesis, Characterization, and Investigation of Antimicrobial Properties of Salt and Metal Complexes of 2,6-Pyridinedicarboxylic Acid and 2-Amino-4,6-dimethylpyridine

Year 2024, Volume: 8 Issue: 2, 115 - 130, 30.12.2024
https://doi.org/10.47137/usufedbid.1480103

Abstract

A new salt (3) of 2,6-pyridinedicarboxylic acid (1) and 2-amino-4,6-dimethylpyridine (2) and the metal complexes of the salt {(H2)x[M(1)2].nH2O, M = Fe (III), x = 1, n = 3 (4); M = Co(II), x = 2, n = 4 (5); M = Ni(II), x = 2, n = 5 (6); M = Cu(II), x = 2, n = 4 (7)} were synthesized. The structures of the compounds were suggested by AAS, IR, UV, magnetic susceptibility and molar conductivity methods. As a result of spectroscopic analysis, it was observed that all metal complexes had an ionic and octahedral structure. All substances were susceptible to Candida albicans (ATCC 14053) (yeast), Pseudomonas. aeruginosa (ATCC 27853), Staphylococcus aureus (NRRL-B 767), Listeria monocytogenes (ATCC 7644), Bacillus subtilis, Enterococcus faecalis (ATCC 29212), and Escherichia coli (ATCC 25922) bacteria were examined. Antimicrobial activity results were compared with Fluconazole, Ketoconazole, Chloramphenicol, Levofloxacin, Vancomycin and Cefepime. In the activity results, the best values were observed 3 in B. subtilis bacteria, 6 and 7 in S. aureus bacteria, 5 7 in P. aeruginoa bacteria, all compounds in L. monocytogenes bacteria, all compounds (except 4) in E. coli bacteria, 2 in E. faecalis bacteria and 4 in C. albicans yeast.

References

  • Braga D, Grepioni F, Novoa JJ, Inter-anion O–H–··· O–hydrogen bond like interactions: the breakdown of the strength–length analogy. Chemical Communication, 1998;18:1959–1960.
  • Desiraju GR, A bond by any other name. Angewandte Chemie, 2011;50:52–59.
  • Aghabozorg H, Mantegh F, Sheshmani S, A brief review on structural concepts of novel supramolecular proton transfer compounds and their metal complexes. Journal of the Iranian Chemical Society, 2008;5(2):184-227.
  • Refat MS, Adam AMA, Saad HA, Utility of charge-transfer complexation for the assessment of macrocyclic polyethers: Spectroscopic, thermal and surface morphology characteristics of two highly crown ethers complexed with acido acceptors. Journal of Molecular Structure, 2015;1085:178–190.
  • Gopi R, Ramanathan N, Sundararajan K, Hydrogen-bonded complexes of acetylene and acetonitrile: A matrix isolation infrared and computational study. Journal of Molecular Structure, 2015;1083:364–373.
  • Al-Ahmary KM, Habeeb M, Al-Solmy EA, Spectroscopic studies of the hydrogen bonded charge transfer complex of 2-aminopyridine with π-acceptor chloranilic acid in different polar solvents, Journal of Molecular Liquids, 2011;162:129–134.
  • Alexeev YE, Kharisov BI, Hermandez TC, Garnovski AD, Coordination motifs in modern supramolecular chemistry. Coordination Chemistry Review, 2010;254:794–831.
  • Celestine MJ, Bullock JL, Boodram S, Rambaran VH, Holder AA, Interesting properties of p-, d-, and f-block elements when coordinated with dipicolinic acid and its derivatives as ligands: their use as inorganic pharmaceuticals. Reviews in Inorganic Chemistr, 2015;35(2):57-67.
  • Kirillov AM, Shul’pin GB, Pyrazinecarboxylic acid and analogs: highly efficient co-catalysts in the metal-complex-catalyzed oxidation of organic compounds. Coordination Chemistry Reviews, 2013;257:732-754.
  • Kirillova MV, Guedes da Silva MFC, Kirillov AM, Frausto da Silva JJR, Pombeiro AJL, 3D hydrogen bonded heteronuclear CoII, NiII, CuII and ZnII aqua complexes derived from dipicolinic acid. Inorganica Chimica Acta, 2007;360:506-512.
  • Marinescu M, 2-Aminopyridine – a classic and trendy pharmacophore. International Journal of Pharma and Bio Sciences, 2017;8(2):338-335.
  • Yenikaya C, Poyraz M, Sarı M, Demirci F, İlkimen H, Büyükgüngör O, Synthesis, characterization and biological evaluation of a novel Cu(II) complex with the mixed ligands 2,6-pyridinedicarboxylicacid and 2-aminopyridine. Polyhedron, 2009;28(16):3526-3532.
  • Yenikaya C, Büyükkıdan N, Sarı M, Keşli R, İlkimen H, Bülbül M, Büyükgüngör O, 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, 2011;64(19):3353-3365.
  • Hakimi M, Motieiyan E, Bertolotti F, Marabello D, Nunes R, Vitor H, Three new bismuth(III) pyridine-2,6-dicarboxylate compounds: Synthesis, characterization and crystalstructures. Journal of Molecular Structure, 2015;1099:523-533.
  • Sharma G, Narula AK, Synthesis and optoelectronic properties of three Eu(III)-dipicolinate complexes based on a-picolinic acid, 2-aminopyridine and 2-hydroxypyridine as secondary ligands. Journal of Materials Science: Materials in Electronics, 2015;26(2):1009-1017.
  • Mirzaei M, Eshtiagh-Hosseini H, Karrabi Z, Molcanov K, Eydizadeh E, Mague JT, Bauza A, Frontera A, Crystal engineering with coordination compounds of NiII, CoII, and CrIII bearing dipicolinic acid driven by the nature of the noncovalent interactions. CrystEngComm, 2014;16(24):5352-5363.
  • Sheshmani S, Ghadermazi M, Motieiyan E, Shokrollahi A, Malekhosseini Z, Fashapoyeh MA, Potentiometric and structural studies of MIIA(Ca, Sr, Ba)-pyridine-2,6-dicarboxylic acid-2-aminopyridine adduct. Journal of Coordination Chemistry, 2013;66(22):3949-3969.
  • Mistri S, Zangrando E, Manna SC, Cu(II) complexes of pyridine-2,6-dicarboxylate and N-donor neutral ligands: Synthesis, crystal structure, thermal behavior, DFT calculation and effect of aromatic compounds on their fluorescence. Inorganica Chimica Acta, 2013;405:331-338.
  • Mirzaei M, Eshtiagh-Hosseini H, Mague JT, 2-Aminopyridinium bis(pyridine-2,6-dicarboxylato)ferrate(III). Acta Crystallographica, Section E: Structure Reports Online, 2012;68(2):m174-m174.
  • Trivedi M, Nagarajan R, Kumar A, Rath NP, A new single pot synthesis of m-bis(oxido)bis{oxidovanadium(V)} dipicolinato complex with 2-aminopyridinium as counter cation: Spectroscopic, structural, catalytic and theoretical studies. Journal of Organometallic Chemistry, 2010;695(12-13):1722-1728.
  • Pramanik S, Konar S, Chakraborty K, Pal T, Das S, Chatterjee S, Dolai M, Pathak S, Investigation of electrical conductance properties, non-covalent interactions and TDDFT calculation of a newly synthesized copper(II) metal complex. Journal of Molecular Structure, 2020;1206:127663.
  • Zohrevandi M, Abdolmaleki S, Ghadermazi M, Gholiee Y, Aliabadi A, Motieiyan E, Hakimi M, Marabello D, Synthesis, characterization, crystallographic structure, theoretical studies, and in vitro cytotoxicity assessment of two Gd(III) and Ce(IV) complexes containing pyridine-2,6-dicarboxylate. Polyhedron, 2022;211:115561.
  • Foroughian M, Foroumadi A, Notash B, Bruno G, Rudbari AH, Aghabozorg H, 2,3-Diaminopyridinium 6-carboxypyridine-2-carboxylate. Acta Crystallographica, Section E: Structure Reports Online, 2011;67(12):o3325-o3325.
  • Aghabozorg H, Kazemi S, Agah AA, Mirzaei M, Notash B, Bis(2,3-diaminopyridinium)bis(m-pyridine-2,6-dicarboxylato)-κ4O2,N,O6:O6,κ4O2:O2,N,O6-bis[aqua(pyridine-2,6-dicarboxylato-κ3O2,N,O6)bismuthate(III)] tetrahydrate. Acta Crystallographica, Section E: Structure Reports Online, 2011;67(3):m360-m361.
  • Moghimi A, Ranjbar M, Aghabozorg H, Jalali F, Shamsipur M, Yap GPA, Rahbarnoohi H, A novel pyridine containing self-assembling system: synthesis, characterization, X-ray crystal structure, 13C solid phase NMR and solution studies. Journal of Molecular Structure, 2002;605(2-3):133-149.
  • Aghabozorg H, Saei AA, Ramezanipour F, 2,6-Diaminopyridinium pyridinium-2,6-dicarboxylate: a redetermination. Acta Crystallographica, Section E: Structure Reports Online, 2005;61(10):o3242-o3244.
  • Jamei MR, Ranjbar M, Eliassi A, Sonochemical synthesis of vanadium complex nano-particles: a new precursor for preparation and evaluation of V2O5/Al2O3 nano-catalyst in selective oxidation of methanol to methylal. Journal of the Iranian Chemical Society, 2017;14(12):2627-2635.
  • Cai M, Gao X, Chen J, Structural refinement and luminescent property of a novel europium(III) complex with a proton transfer compound containing 2,6-pyridinedicarboxylate and 2,6-pyridinediammonium ligands synthesized by ultrasonic method. Journal of Molecular Structure, 2015;1086:93-98.
  • Chen J, Gao X, Cai M, Hydrogen bond-type europium complex fluorescent material with high fluorescence intensity and good thermal stability, and preparation method thereof. Faming Zhuanli Shenqing, CN 103694266 A 20140402, 2014.
  • Tabatabaee M, Tahriri M, Tahriri M, Dusek M, Fejfarova K, Bis(2,6-diaminopyridinium) bis(pyridine-2,6-dicarboxylato)zincate(II) monohydrate. Acta Crystallographica, Section E: Structure Reports Online, 2011;67(6):m769-m770.
  • Cai M, Chen J, Wu Q, Ma X, Yang J, Li F, Preparation of hydrogen bond-type rare earth metal complex as antibacterial agents. Faming Zhuanli Shenqing, CN 101456875 A 20090617, 2009.
  • Aghabozorg H, Saei AA, Moghimi A, Ramezanipour F, Synthesis and crystal structure of a novel six-coordinate gallium(III) complex Majallah-i Bulurshinasi va Kanishinasi-i Iran, 2005;13(1):185-194.
  • Aghabozorg H, Saei AA, Sadr-Khanlou E, Moghimi A, Crystal structure of 2,6-diaminopyridinium bis(2,6-pyridinedicarboxylato)antimonate(III) trihydrate hemichloroform. X-Ray Structure Analysis Online, 2005;21(11):x207-x208.
  • Rafizadeh M, Amani V, Dihydronium bis(2,6-diaminopyridinium) tris(pyridine-2,6-dicarboxylato-κ3O,O',N)dysprosate(III) dihydrate. Acta Crystallographica, Section E: Structure Reports Online, 2006;62(1):m90-m91.
  • Aghabozorg H, Ramezanipour F, Kheirollahi PD, Saei AA, Shokrollahi A, Shamsipur M, Manteghi F, Soleimannejad J, Sharif MA, Novel complexes of gallium(III), indium(III), and thallium(III) with pyridine-containing proton transfer ion pairs obtained from dipicolinic acid - synthesis, characterization and x-ray crystal structure. Zeitschrift fuer Anorganische und Allgemeine Chemie, 2006;632(1):147-154.
  • Ssheshmani S, Kheirollahi D, Aghabozorg H, Shokrollahi A, Kickelbick G, Shamsipur M, Ramezanipour F, Moghimi A, Synthesis and crystal structure of CeIII and BiIII complexes and solution studies of ZnII, CdII, PbII, CeIII, and BiIII complexes obtained from proton transfer compounds containing 2,6-pyridinedicarboxylate ion. Zeitschrift fuer Anorganische und Allgemeine Chemie, 2005;631(15):3058-3065.
  • Rafizadeh M, Ranjbar M, Amani V, Crystal structure of gadolinium(III) complex, dihydronium (2,6-pyridinediamonium) tris-(2,6-pyridinedicarboxylato)gadolinate(III) dihydrate, C31H34GdN9O16. Analytical Sciences: X-ray Structure Analysis Online, 2005;21(7):x113-x114.
  • Aghabozorg H, Moghimi A, Manteghi F, Ranjbar M, A nine-coordinated ZrIV complex and a self-assembling system obtained from a proton transfer compound containing 2,6-pyridinedicarboxylate and 2,6-pyridinediammonium, synthesis and x-ray crystal structure. Zeitschrift fuer Anorganische und Allgemeine Chemie, 2005;631(5):909-913.
  • Ranjbar M, Aghbozorg H, Crystal structure of a polymeric Hg(II) complex of a pyridine containing a self-assembly system. Analytical Sciences: X-ray Structure Analysis Online, 2004;20(4):x153-x154.
  • Ranjbar M, Crystal structure of a five-coordinate vanadium(V) complex, 2,6-diaminopyridinum 2,6-pyridinedicarboxylatodioxovanadate(V) Analytical Sciences: X-ray Structure Analysis Online, 2004;20(July-Sept):x135-x136.
  • Ghamari S, Ranjbar M, Preparation, characterization, and the study of the electrochemical behavior of Y-doped Bariumcerate powders by new precursors. Hydrogen, Fuel Cell & Energy Storage, 2023;10:1-10.
  • Ranjbar M, Abdollahi M, Rafizadeh M, Crystal structure of a seven-coordinate thallium(III) complex, 2,6-diaminopyridinumbis(2,6-pyridinedicarboxylato)aquathallate(III)tetrahydrate Analytical Sciences: X-ray Structure Analysis Online, 2004;20(July-Sept):x133-x134.
  • Moghimi A, Shokrollahi A, Shamsipur M, Aghabozorg H, Ranjbar M, X-ray crystal structure and solution studies of hexacoordinated mercury (II) complex of a pyridine containing proton transfer compound. Journal of Molecular Structure, 2004;701(1-3):49-56.
  • Rafizadeh M, Ranjbar M, Amani V, Dihydronium 2,6-diaminopyridinium tris(2,6-pyridinedicarboxylato)ytterbate(III) dihydrate. Acta Crystallographica, Section E: Structure Reports Online, 2004;60(4):m479-m481.
  • Ranjbar M, Aghabozorg H, Moghimi A, Crystal structure of bis(2,6-diaminopyridinium) diaqua-bis-m-(2,6-pyridinedicarboxylato)-bis(2,6-pyridinedicarboxylato)dibismuthate(III) tetrahydrate, (C28H16O18N4Bi2)(C5H8N3)2.4H2O. Zeitschrift fuer Kristallographie - New Crystal Structures, 2003;218(4):432-434.
  • Moghimi A, Ranjbar M, Aghabozorg H, Jalali F, Shamsipur M, Chadha KK, Synthesis, characterization, and X-ray crystal structures of Co(II) and La(III) complexes of a pyridine containing self-assembling system and solution studies of the Co(II) complex. Canadian Journal of Chemistry, 2002;80(12):1687-1696.
  • Moghimi A, Ranjbar M, Aghabozorg H, Jalali F, Shamsipur M, Chadah RK, Synthesis, NMR characterization, x-ray crystal structure and solution studies of Ni(II) complexes of a pyridine containing self-assembling system. Journal of Chemical Research, Synopses, 2002;(10):477-479, 1047-1065.
  • Ranjbar M, Moghimi A, Aghabozorg H, Yap GPA, Crystal structure of zinc(II) complex of a pyridine containing self-assembling system. Analytical Sciences, 2002;18(2):219-220.
  • Ranjbar M, Aghabozorg H, Moghimi A, Yanovsky A, Crystal structure of 2,6-diaminopyridinium bis(2,6-pyridinedicarboxylato)chromium(III) 2,6-pyridinedicarboxylic acid hemihydrate, C26H18CrN6O12.0.5H2O. Zeitschrift fuer Kristallographie - New Crystal Structures, 2001;216(4):626-628.
  • Hejrani-Dalir A, Tabatabaee M, Sheibani A, Synthesis and crystal structure of 2-amino-3-hydroxypyridinium dioxido(pyridine-2,6-dicarboxylato-κ3O2,N,O6)vanadate(V) and its conversion to nanostructured V2O5. Acta Crystallographica, Section C: Structural Chemistry, 2015;71(2):89-92.
  • İlkimen H, Salün SG, Gülbandılar A, Sarı M, 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, 2022;1270:133961.
  • Sharif MA, Tabatabaee M, Adinehloo M, Aghabozorg H, 2-Amino-4-methylpyridinium 6-carboxypyridine-2-carboxylate sesquihydrate. Acta Crystallographica, Section E: Structure Reports Online, 2010;66(12):o3232-o3232.
  • Aghabozorg H, Rouchi AM, Mirzaei M, Notash B, 2-Amino-4-methylpyridinium 6-carboxypyridine-2-carboxylate methanol monosolvate. Acta Crystallographica, Section E: Structure Reports Online, 2011;67(1):o54-o54.
  • Cai M, Chen J, A new ultrasonic synthetic method for proton transfer compound of 2,6-pyridinedicarboxylic acid and 2,6-pyridinediamine. Youji Huaxue, 2010;30(7):1076-1079.
  • Aghabozorg H, Rouchi MA, Notash B, Mirzaei M, Bis(2-amino-4-methylpyridinium) bis(pyridine-2,6-dicarboxylato)cuprate(II) Acta Crystallographica, Section E: Structure Reports Online, 2011;67(2):m189-m189.
  • Mirzaei M, Eshtiagh-Hosseini H, Alfi N, Aghabozorg H, Gharamaleki JA, Beyramabadi SA, Khavasi HR, Salimi AR, Shokrollahi A, Aghaei R, Karami E, Syntheses, crystal, molecular structures, and solution studies of Cu(II), Co(II), and Zn(II) coordination compounds containing pyridine-2,6-dicarboxylic acid and 1,4-pyrazine-2,3-dicarboxylic acid: comparative computational studies of Cu(II) and Zn(II) complexes. Structural Chemistry, 2011;22(6):1365-1377.
  • Eshtiagh-Hosseini H, Aghabozorg H, Mirzaei M, Amini MM, Chen YG, Shokrollahi A, Aghaei R, Diversity in coordination behavior of dipicolinic acid with lead(II), calcium(II), and nickel(II) in the presence of pyrazine and 2-amino-4-methylpyridine spacers in construction of three supramolecular architectures. Journal of Molecular Structure, 2010;973(1-3):180-189.
  • Movahedi E, Razmazma H, Rezvani A, Nowroozi A, Ebrahimi A, Eigner V, Dusek M, Arjmand F, A novel Cu(II)-based DNA-intercalating agent: Structural and biological insights using biophysical and in silico techniques. Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy, 2023;293:122438.
  • Mirzaei M, Eshtiagh-Hosseini H, Karrabi Z, Notash B, Bauza A, Frontera A, Synthesis, structure and DFT study of a chelidamic acid based Cu coordination polymer: On the importance of π-π interactions and hexameric water clusters. Journal of Molecular Structure, 2015;1080:30-36.
  • Pasdar H, Ebdam A, Aghabozorg H, Notash B, Bis(2-amino-6-methylpyridinium) tris(pyridine-2,6-dicarboxylato)zirconate(IV) dihydrate. Acta Crystallographica, Section E: Structure Reports Online, 2011;67(3):m294, Sm294/1-Sm294/11.
  • Eshtiagh-Hosseini H, Yousefi Z, Shafiee M, Mirzaei M, Fe(III) and cobalt(II) coordination compounds of 5-bromo-6-methyl-2-morpholinepyrimidinium-4-amine pyridine-2,6-dicarboxylate, Journal of Coordination Chemistry, 2010;63(18):3187-3197.
  • Cook D, Vibrational spectra of yridinium salts Canadian Journal of Chemistry, 1961;39(10):2009-2024.
  • Nakamoto K, Infrared and raman spectra of inorganic and coordination compounds 5th ed NewYork: Wiley-Interscience, pp 232, 1997.
  • Geary WJ, The use of conductivity measurements in organic solvents for the characterisation of coordination compounds, Coordination Chemistry Reviews, 1971;7(1):81-122.
  • İlkimen H, Gülbandılar A, Synthesis, characterization, anti-microbial activity studies of 2-methoxy-5-sulfamoylbenzoic acid and 2-aminopyridine derivatives salts and their Cu(II) complexes. Pamukkale University Journal of Engineering Sciences, 2024; Doi. 10.5505/pajes.2024.48196.
  • İlkimen H, Gülbandılar A, Synthesis, characterization, anti-microbial activity studies of salicylic acid and 2-aminopyridine derivatives salts and their Cu(II) complexes. Journal of Scientific Reports-A, 2024;56:94-104.
There are 66 citations in total.

Details

Primary Language English
Subjects Structural Biology
Journal Section Research Article
Authors

Elif Yurt 0009-0000-7309-3963

Halil İlkimen 0000-0003-1747-159X

Beyza Yılmaz 0009-0007-0756-6305

Ayşe Polat 0009-0003-6048-7850

Aysel Gülbandılar 0000-0001-9075-9923

Publication Date December 30, 2024
Submission Date May 8, 2024
Acceptance Date August 15, 2024
Published in Issue Year 2024 Volume: 8 Issue: 2

Cite

APA Yurt, E., İlkimen, H., Yılmaz, B., Polat, A., et al. (2024). Synthesis, Characterization, and Investigation of Antimicrobial Properties of Salt and Metal Complexes of 2,6-Pyridinedicarboxylic Acid and 2-Amino-4,6-dimethylpyridine. Uşak Üniversitesi Fen Ve Doğa Bilimleri Dergisi, 8(2), 115-130. https://doi.org/10.47137/usufedbid.1480103
AMA Yurt E, İlkimen H, Yılmaz B, Polat A, Gülbandılar A. Synthesis, Characterization, and Investigation of Antimicrobial Properties of Salt and Metal Complexes of 2,6-Pyridinedicarboxylic Acid and 2-Amino-4,6-dimethylpyridine. Uşak Üniversitesi Fen ve Doğa Bilimleri Dergisi. December 2024;8(2):115-130. doi:10.47137/usufedbid.1480103
Chicago Yurt, Elif, Halil İlkimen, Beyza Yılmaz, Ayşe Polat, and Aysel Gülbandılar. “Synthesis, Characterization, and Investigation of Antimicrobial Properties of Salt and Metal Complexes of 2,6-Pyridinedicarboxylic Acid and 2-Amino-4,6-Dimethylpyridine”. Uşak Üniversitesi Fen Ve Doğa Bilimleri Dergisi 8, no. 2 (December 2024): 115-30. https://doi.org/10.47137/usufedbid.1480103.
EndNote Yurt E, İlkimen H, Yılmaz B, Polat A, Gülbandılar A (December 1, 2024) Synthesis, Characterization, and Investigation of Antimicrobial Properties of Salt and Metal Complexes of 2,6-Pyridinedicarboxylic Acid and 2-Amino-4,6-dimethylpyridine. Uşak Üniversitesi Fen ve Doğa Bilimleri Dergisi 8 2 115–130.
IEEE E. Yurt, H. İlkimen, B. Yılmaz, A. Polat, and A. Gülbandılar, “Synthesis, Characterization, and Investigation of Antimicrobial Properties of Salt and Metal Complexes of 2,6-Pyridinedicarboxylic Acid and 2-Amino-4,6-dimethylpyridine”, Uşak Üniversitesi Fen ve Doğa Bilimleri Dergisi, vol. 8, no. 2, pp. 115–130, 2024, doi: 10.47137/usufedbid.1480103.
ISNAD Yurt, Elif et al. “Synthesis, Characterization, and Investigation of Antimicrobial Properties of Salt and Metal Complexes of 2,6-Pyridinedicarboxylic Acid and 2-Amino-4,6-Dimethylpyridine”. Uşak Üniversitesi Fen ve Doğa Bilimleri Dergisi 8/2 (December 2024), 115-130. https://doi.org/10.47137/usufedbid.1480103.
JAMA Yurt E, İlkimen H, Yılmaz B, Polat A, Gülbandılar A. Synthesis, Characterization, and Investigation of Antimicrobial Properties of Salt and Metal Complexes of 2,6-Pyridinedicarboxylic Acid and 2-Amino-4,6-dimethylpyridine. Uşak Üniversitesi Fen ve Doğa Bilimleri Dergisi. 2024;8:115–130.
MLA Yurt, Elif et al. “Synthesis, Characterization, and Investigation of Antimicrobial Properties of Salt and Metal Complexes of 2,6-Pyridinedicarboxylic Acid and 2-Amino-4,6-Dimethylpyridine”. Uşak Üniversitesi Fen Ve Doğa Bilimleri Dergisi, vol. 8, no. 2, 2024, pp. 115-30, doi:10.47137/usufedbid.1480103.
Vancouver Yurt E, İlkimen H, Yılmaz B, Polat A, Gülbandılar A. Synthesis, Characterization, and Investigation of Antimicrobial Properties of Salt and Metal Complexes of 2,6-Pyridinedicarboxylic Acid and 2-Amino-4,6-dimethylpyridine. Uşak Üniversitesi Fen ve Doğa Bilimleri Dergisi. 2024;8(2):115-30.