SavedAdd your journal

Journals / Uşak Üniversitesi Fen ve Doğa Bilimleri Dergisi / 2025 / Cilt: 9 Sayı: 2

Synthesis, Characterization, Investigation of Antibacterial and Antifungal Properties of Cu(II) Complexes of 2-Aminopicoline Derivatives and 4-Chloro-3-sulfamoylbenzoic Acid

2-Aminopikolin Türevleri ile 4-Kloro-3-sülfamoyilbenzoik Asitin Cu(II) Komplekslerinin Sentezi, Karakterizasyonu, Antibakteriyel ve Antifungal Özelliklerinin İncelenmesi

Halil İlkimen(KÜTAHYA DUMLUPINAR ÜNİVERSİTESİ)0000-0003-1747-159X
Cengiz Yenikaya(KÜTAHYA DUMLUPINAR ÜNİVERSİTESİ)0000-0002-5867-9146
Aysel Gülbandılar(ESKİŞEHİR OSMANGAZİ ÜNİVERSİTESİ)0000-0001-9075-9923
Pages
184–195
Publication Date
2025-12-30
🏛️Bibliographic metadata and full text access for this article are provided via DergiPark.
DergiPark Record ↗
✨

AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

The best activity values of the compounds are 1 and 2 for S. aureus bacteria, 5 for E. coli bacteria, 7 for P. aeruginosa bacteria, 2 for L. monocytogenes bacteria, all compounds for E. faecalis bacteria, 8 for B. subtilis bacteria, and 1 for C. albicans yeast.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:In this study, proton transfer salts (1-4) of 4-chloro-3-sulfamoylbenzoic acid (5) with 2-amino-X-picoline {X = 3 (6), 4 (7), 5 (8) ve 6 (9)} were synthesized.
📊
Key Findings & Data:The structures of the synthesized compounds were elucidated by AAS, elemental analysis, IR, UV, molar conductivity and magnetic susceptibility methods.
💡
Conclusion & Impact:The best activity values of the compounds are 1 and 2 for S. aureus bacteria, 5 for E. coli bacteria, 7 for P. aeruginosa bacteria, 2 for L. monocytogenes bacteria, all compounds for E. faecalis bacteria, 8 for B. subtilis bacteria, and 1 for C. albicans yeast.
🔬Design:Araştırma Makalesi
📍Scope:Comprehensive Sample
⚙️Variables:4-Kloro-3-sülfamoyilbenzoik asit · 2-aminopikolin · Cu(II) kompleks

Abstract

In this study, proton transfer salts (1-4) of 4-chloro-3-sulfamoylbenzoic acid (5) with 2-amino-X-picoline {X = 3 (6), 4 (7), 5 (8) ve 6 (9)} were synthesized. The structures of the synthesized compounds were elucidated by AAS, elemental analysis, IR, UV, molar conductivity and magnetic susceptibility methods. All substances used are susceptible to the yeast Candida albicans, Listeria monocytogenes, Staphylococcus aureus, Enterococcus faecalis, Bacillus subtilis, Escherichia coli and Pseudomonas aeruginosa. Their antimicrobial activities against bacteria were examined. Their antimicrobial activity results were comparison with Fluconazole, Ketoconazole, Chloramphenicol, Levofloxacin, Vancomycin and Cefepime. The best activity values of the compounds are 1 and 2 for S. aureus bacteria, 5 for E. coli bacteria, 7 for P. aeruginosa bacteria, 2 for L. monocytogenes bacteria, all compounds for E. faecalis bacteria, 8 for B. subtilis bacteria, and 1 for C. albicans yeast.

Özet

Bu çalışmada 4-kloro-3-sülfamoyilbenzoik asit (5) ile 2-amino-X-pikolin’in {X = 3 (6), 4 (7), 5 (8) ve 6 (9)} Cu(II) kompleksleri (1-4) sentezlenmiştir. Sentezlenen bileşiklerin yapıları, AAS, elementel analiz, IR, UV, molar iletkenlik ve manyetik duyarlılık metotları ile aydınlatılmıştır. Sentezlenen ve kullanılan maddelerin Candida albicans mayasına, Staphylococcus aureus, Bacillus subtilis, Enterococcus faecalis, Listeria monocytogenes, Pseudomonas aeruginosa ve Escherichia coli bakterilerine karşı antimikrobiyal aktiviteleri incelenmiştir. Antimikrobiyal aktivite sonuçları Flukonazol, Ketokonazol, Kloramfenikol, Levofloksasin, Vankomisin ve Sefepim ile kıyaslanmıştır. Bileşiklerin en iyi aktivite değerleri S. aureus bakterilerinde 1 ve 2, E. coli bakterisinde 5, P. aeruginoa bakterisinde 7, L. monocytogenes bakterisinde 2, E. faecalis bakterisinde tüm bileşikler, B. subtilis bakterisinde 8 ve C. albicans mayasında 1 gözlenmiştir.

🔖

Cite This Article

İlkimen, H., Yenikaya, C., Gülbandılar, A. (2025). Synthesis, Characterization, Investigation of Antibacterial and Antifungal Properties of Cu(II) Complexes of 2-Aminopicoline Derivatives and 4-Chloro-3-sulfamoylbenzoic Acid. Uşak Üniversitesi Fen ve Doğa Bilimleri Dergisi, Cilt: 9 Sayı: 2, 184–195. https://doi.org/10.47137/usufedbid.1702755

📄 Full Text PDF Viewer

📄

PDF görüntüleyici hazırlanıyor...

References (49)

  1. Marinescu M. 2-Aminopyridine – a classic and trendy pharmacophore, International Journal of Pharmacy and Biological Sciences, 2017;8(2):338-355.
  2. Mochida E, Suzuki Y, Yamaguchi K, Ohnishi H. Antiviral compositions containing aminosulfonylhalobenzoic acid derivatives, France patent FR2493702 A1, 1982:1982-05-14.
  3. Kavitha C, Narendra K, Ratnakar A, Poojith N, Sampath C, Banik S, Suchetan PA, Potla KM, Naidu NV. An analysis of structural, spectroscopic signatures, reactivity and anti-bacterial study of synthetized 4-chloro-3-sulfamoylbenzoic acid, Journal of Molecular Structure, 2020;1202:127176.
  4. İlkimen H, Salün SG, İlkimen B, Yenikaya C. 4-Kloro-3-sülfamoyilbenzoik asitin Mg(II), Fe(II) ve Co(II) metal komplekslerinin sentezi ve karakterizasyonu, Euroasia Journal of Mathematics, Engineering, Natural & Medical Sciences, 2020;7(13):213-219.
  5. İlkimen H, Salün SG, İlkimen B, Yenikaya C. 4-Kloro-3-sülfamoyilbenzoik asitin Ni(II), Cu(II) ve Cd(II) metal komplekslerinin sentezi ve karakterizasyonu, Euroasia Journal of Mathematics, Engineering, Natural & Medical Sciences, 2020;7(13):220-226.
  6. İlkimen H, Salün SG, Yenikaya C. Sülfamoyilbenzoik asit türevlerinin Fe(III) metal komplekslerinin sentezi ve karakterizasyonu, Euroasia Journal of Mathematics, Engineering, Natural & Medical Sciences, 2020;7(8):108-116.
  7. Brzozowski Z, Slawinski J. Preparation of 1,1-dioxo-3-mercapto-1,4,2-benzodithiazines as drugs, Poland patent PL134567 B1, 1985;1985-08-31.
  8. Hu Y, Dai R, An J, Qian Q, Deng Y. Binding interaction of carbonic anhydrase-liposome complex and medicinal molecules by Scatchard method, Keji Daobao, 2015;33(17):96-101.
  9. Masuzawa K, Okamura H, Okubo H, Abe Y, Miyaji H, Yamanaka S. Preparation of sulfamoylbenzamide derivatives as diuretics and antihypertensives, Japan, JP62255479 A 1987;1987-11-07.
  10. Khiat M, Bali JP, Guibert MS, Chanal JL, Marignan R. Radiocompetitive determination of a sulfamide diuretic, 3-sulfamido-4-chlorobenzoic acid, using carbonic anhydrase, Clinica Chimica Acta, 1978;82(3):241-247.
  11. Ziemer F, Willms L, Auler T, Bieringer H, Rosinger C. Preparation of acylsulfamoylbenzoic acid amides as herbicide safeners, World Intellectual Property Organization patent 9916744 A1, 1999;1999-04-08.
  12. 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.
  13. Zordok WA, Sadeek SA, El-Farargy AF. Synthesis, characterization, DFT modeling and biological studies of new Co(II), Ni(II) and Cu(II) 4,6-bis(4-chlorophenyl)-2-amino-1,2-dihydropyridine-3-carbinitrile complexes, Journal of the Iranian Chemical Society, 2017;14(12):2529-2547.
  14. Boissier JR, Dumont C, Lesbros J. Diuretic activity of 3-sulfamido-4-chlorobenzoic acid (SD 141.08) and of 3-sulfamido-4-chlorobenzamide (SD 141.12), Therapie, 1966;21(2):331-340.
  15. Zhao F, Dong H, Liu BB, Zhang G, Huang H, Hu H, Liu Y, Kang Z. Tuning luminescence via transition metal-directed strategy in coordination polymers, CrystEngComm, 2014;16(21):4422-4430.
  16. İlkimen H. Synthesis and characterization of mixed ligand Cu(II) complexes of 2-methoxy-5-sulfamoylbenzoic acid and 2 aminopyridine derivatives, Macedonian Journal of Chemistry and Chemical Engineering, 2019;38(1):13-17.
  17. İlkimen H, Türken N, Gülbandılar A. 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, 2021;18:1941-1946.
  18. İlkimen H, Gülbandılar A. Synthesis and characterization of metal complexes of 2,4-dichloro-5-sulfamoylbenzoic acid, International Journal of Chemical Studies, 2022;6(1):29-37.
  19. İlkimen H, Gülbandılar A. 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, 2023;50(3A):1-11.
  20. İlkimen H, Gülbandılar A. 2-Amino-5-substitüepiridin türevleri ile 2-metoksi-5-sulfamoyilbenzoik asitin proton transfer tuzlarının sentezi, karakterizasyonu, antimikrobiyal ve antifungal aktivitelerinin incelenmesi, In: 2nd International Conference on Contemporary Academic Research ICCAR 2023, Konya, Türkiye, 2023:40-47.
  21. İlkimen H, Gülbandılar A. 2-Amino-6-substitüepiridin türevleri ile 2-metoksi-5-sulfamoyilbenzoik asitin proton transfer tuzlarının sentezi, karakterizasyonu, antimikrobiyal ve antifungal aktivitelerinin incelenmesi, In: 2nd International Conference on Contemporary Academic Research ICCAR 2023, Konya, Türkiye, 2023:36-39.
  22. İlkimen H, Yenikaya C. 2,4-Dikloro-5-sülfamoyilbenzoik asit ile 2-aminopiridin türevlerinin karışık ligandlı Cu(II) komplekslerinin sentezi ve karakterizasyonu, Euroasia Journal of Mathematics, Engineering, Natural & Medical Sciences, 2021;8(14):96-103.
  23. İlkimen H, Yenikaya C. 2,4-Dikloro-5-sülfamoyilbenzoik asit ile 2-aminopiridin türevlerinin karışık ligandlı Cu(II) komplekslerinin sentezi ve karakterizasyonu, In: Hodja Akhmet Yassawi 4th International Conference on Scientific Research, Ankara, Türkiye, 2021:197-198.
  24. İlkimen H, Yenikaya C. 2,4-Dikloro-5-sülfamoyilbenzoik asit ile aminometilpiridin türevlerinin Cu(II) komplekslerinin sentezi ve karakterizasyonu, In: 2nd International Conference on Recent Academic Studies, Konya, Türkiye, 2023:37-40.
  25. İlkimen H, Salün SG, Yenikaya C. 2-Metoksi-5-sülfamoyilbenzoik asitin metal komplekslerinin sentezi ve karakterizasyonu, In: SOCRATES 1st International Health, Engineering and Applied Sciences Congress, Ankara, Türkiye, 2021:8-9.
  26. İlkimen H, Yenikaya C, Gülbandılar A. 2-Metoksi-5-sulfamoyilbenzoik asitin metal komplekslerinin antimikrobiyal ve antifungal aktivitelerinin incelenmesi, In: III. Baskent International Conference On Multidisciplinary Studies, Ankara, Türkiye, 2022:97-104.
  27. İlkimen H, Yenikaya C, Gülbandılar A. 2-Metoksi-5-sulfamoyilbenzoik asit ile 2,3-diaminopiridin türevlerinin proton transfer tuzları ve Cu(II) komplekslerinin sentezi, karakterizasyonu, antimikrobiyal özelliklerinin incelenmesi, In: III. Baskent International Conference On Multidisciplinary Studies, Ankara, Türkiye, 2022:105-119.
  28. İlkimen H, Yenikaya C, Gülbandılar A. 2-Aminopiridin türevleri ile 2-metoksi-5-sülfamoyilbenzoik asit tuzlarının sentezi, karakterizasyonu, antimikrobiyal aktivitelerinin incelenmesi, Selçuk Üniversitesi Fen Fakültesi Fen Dergisi, 2022;49(2):53-63.
  29. İlkimen H, Yenikaya C, Gülbandılar A. 2-Metoksi-5-sulfamoyilbenzoik Asit İle 2-Aminonitropiridin türevlerinin sentezi, karakterizasyonu, antimikrobiyal ve antifungal aktivitelerinin incelenmesi, In: 3rd International Conference on Innovative Academic Studies, Konya, Türkiye, 2023:784-793.
  30. Yenikaya C, Sarı M, Bülbül M, İlkimen H, Çelik H, Büyükgüngör O. Synthesis, characterization and antiglaucoma activity of a novel proton transfer compound and a mixed-ligand Zn(II) complex, Bioorganic & Medicinal Chemistry, 2010;18(2):930-938.
  31. Yenikaya C, Sarı M, Bülbül M, İlkimen H, Çınar B, Büyükgüngör O. Synthesis and characterization of two novel proton transfer compounds and their inhibition studies on Carbonic Anhydrase isoenzymes, Journal of Enzyme Inhibition and Medicinal Chemistry, 2011;26(1):104-114.
  32. İlkimen H, Gülbandılar A. Synthesis, characterization, anti-microbial activity studies of 2-methoxy-5-sulfamoylbenzoic acid and 2-amino-5/6-picoline salts and their Cu(II) complexes, Uşak Üniversitesi Fen ve Doğa Bilimleri Dergisi, 2024;8(1):1-14.
  33. 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 Üniversitesi Mühendislik Bilimleri Dergisi, 2024;30(7):1009-1018.
  34. Kaplancıklı ZA, Turan-Zitouni G, Özdemir A, Revial G, Güven K. Synthesis and antimicrobial activity of some thiazolyl-pyrazoline derivatives, Phosphorus, Sulfur, and Silicon and the Related Elements, 2007;182(4):749-764.
  35. Kaplancıklı ZA, Turan-Zitouni G, Özdemir A, Güven K. Synthesis and study of antibacterial and antifungal activities of novel 2-[[(benzoxazole/ benzimidazole2yl)sulfanyl] acetylamino]thiazoles, Archives of Pharmacal Research, 2004;27(11):1081-1085.
  36. Nakamoto K. Infrared and raman spectra of inorganic and coordination compounds. 5th ed. New York: Wiley-Interscience; 1997. p. 231.
  37. El-Behery M, El-Twigry H. Synthesis, magnetic, spectral, and antimicrobial studies of Cu(II), Ni(II) Co(II), Fe(III), and UO2(II) complexes of a new Schiff base hydrazone derived from 7-chloro-4-hydrazinoquinoline, Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy, 2007;66(1):28-36.
  38. Patel KS, Patel JC, Dholariya HR, Patel KD. Multiple heating rate kinetic parameters, thermal, X-ray diffraction studies of newly synthesized octahedral copper complexes based on bromo-coumarins along with their antioxidant, anti-tubercular and antimicrobial activity evaluation, Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy, 2012;96:468-479.
  39. Geary WJ. The use of conductivity measurements in organic solvents for the characterisation of coordination compounds, Coordination Chemistry Reviews, 1971;7(1):81-122.
  40. Spampinato C, Leonardi D. Candida infections, causes, targets, and resistance mechanisms: traditional and alternative antifungal agents, BioMed Research International, 2013;2013(1):204237.
  41. Brunton LL, Hilal-Dandan R, Knollmann BC. eds Goodman & Gilman's: the pharmacological basis of therapeutics. 13th ed. New York: McGraw-Hill Education, 2018.
  42. Koyama N, Inokoshi J, Tomoda H. Anti-infectious agents against MRSA. Molecules, 2012;18(1):204-224.
  43. Anderson VR, Perry CM. Levofloxacin A review of its use as a high-dose, short-course treatment for bacterial infection, Drugs, 2008;68(4):535-565.
  44. Rivera CG, Narayanan PP, Patel R, Estes LL. Impact of cefepime susceptible-dose-dependent MIC for enterobacteriaceae on reporting and prescribing, Antimicrobial Agents and Chemotherapy, 2016;60(6):3854-3855.
  45. Vince R, Almquist RG, Ritter CL, Daluge S. Chloramphenicol binding site with analogues of chloramphenicol and puromycin, Antimicrobial Agents and Chemotherapy, 1975;8:439-443.
  46. Van Tyle JH. Ketoconazole: Mechanism of action, spectrum of activity, pharmacokinetics, drug interactions, adverse reactions and therapeutic use, Pharmacotherapy, 1984;4(6):343-73.
  47. Tweedy BG. Synthesis and assessment of antibacterial activities of ruthenium(III) mixed ligand complexes containing 1,10-phenanthroline and guanide, Phytopathology, 1964;55:910-914.
  48. Chohan ZH, Arif M, Akhtar MA, Supuran C. Metal-based antibacterial and antifungal agents: synthesis, characterization, and in vitro biological evaluation of Co(II), Cu(II), Ni(II), and Zn(II) complexes with amino acid-derived compounds, Bioinorganic Chemistry and Applications, 2006;2006:83131.
  49. Raman N, Raja SJ, Sakthivel A. Transition metal complexes with Schiff-base ligands: 4-aminoantipyrine based derivatives–a review, Journal of Coordination Chemistry, 2009;62(5):691-709.