Pamukkale Univ Muh Bilim Derg. Ahead of Print: PAJES-48196 | DOI: 10.5505/pajes.2024.48196

Synthesis, characterization, anti-microbial activity studies of 2-methoxy-5-sulfamoylbenzoic acid and 2-aminopyridine derivatives salts and their Cu(II) complexes

Halil Ýlkimen¹, Aysel Gülbandýlar^2
1Kütahya Dumlupinar University
²Eskiþehir Osmangazi University

Two new salts (4 and 5) obtained between 2-methoxy-5-sulfamoylbenzoic acid (1) and 2-aminopyridine (2) or 2-amino-4-methylpyridine (3), and their Cu(II) complexes (6 and 7) have been obtained. The structures of the salts (4 and 5) were suggested by elemental analysis, NMR, FT-IR and UV-Vis, while the structures of Cu(II) complexes (6 and 7) were suggested by elemental analysis, AAS, UV-Vis and magnetic susceptibility techniques. While the acid: base ratio was 2: 1 for 4 and 1: 1 for 5 salts, the metal: acid: base ratio was 1: 2: 2 for 6 and 7. According to the results of spectroscopic analysis, the structures of 6 and 7 compounds were proposed as octahedral. Additionally, antimicrobial activities of all compounds were studied against Pseudomonas aeruginosa (ATCC 27853), Staphylococcus aureus (NRRL B-767), Bacillus subtilis, Enterococcus faecalis (ATCC 29212), Escherichia coli (ATCC25922) and Listeria monocytogenes (ATCC 7644) bacteria and Candida albicans (F89) yeast. The results were comparisoned with the antibiotics (Fluconazole, Vancomycin, Cefepime and Levofloxacin). All compounds showed activity against bacteria and yeasts. Compounds Cu(OAc)2.2H2O (31.25 µg/mL) for C. Albicans, 1 and 7 (31.25 µg/mL) for L. monocytogens, all compounds (except 6) (7.60 µg/mL) for B. subtilis, 2 (31.25 µg/mL) for E. Coli, 7 (15.60 µg/mL) for S. aureus, 7 (31.25 µg/mL) for E. Faecalis, and 3 (15.60 µg/mL) for P. aeruginoa have the best activity.

Keywords: 2-Aminopyridine, 2-Methoxy-5-sulfamoylbenzoic Acid, Salt, Cu(II) Complexes, Anti-microbial Activity

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2-Metoksi-5-sülfamoilbenzoik asit ve 2-aminopiridin türevlerinin tuzlarý ve bunlarýn Cu(II) komplekslerinin sentezi, karakterizasyonu, antimikrobiyal aktivite çalýþmalarý

Halil Ýlkimen¹, Aysel Gülbandýlar^2
1Kütahya Dumlupýnar Üniversitesi
²Eskiþehir Osmangazi Üniversitesi

2-Metoksi-5-sülfamoilbenzoik asit (1) ve 2-aminopiridin (2) veya 2-amino-4-metilpiridin (3) reaksiyonundan iki yeni tuz (4 ve 5) ve bunlarýn Cu(II) kompleksleri (6 ve 7) elde edildi. Tuzlarýn (4 ve 5) yapýlarý element analizi, NMR, FT-IR ve UV-Vis ile aydýnlatýlýrken, Cu(II) komplekslerinin (6 ve 7) yapýlarý element analizi, AAS, UV-Vis ve manyetik duyarlýlýk teknikleri ile önerildi. Asit: baz oraný 4 tuz için 2: 1 ve 5 tuz için 1: 1 iken, metal: asit: baz oraný 6 ve 7 için 1: 2: 2 ‘dir. Spektroskopik analiz sonuçlarýna göre 6 ve 7 bileþik oktahedral olarak önerildi. Ayrýca tüm bileþiklerin antimikrobiyal aktiviteleri Pseudomonas aeruginosa (ATCC 27853), Staphylococcus aureus (NRRL B-767), Bacillus subtilis, Enterococcus faecalis (ATCC 29212), Escherichia coli (ATCC25922) ve Listeria monocytogenes (ATCC 7644) bakterilerine ve Candida albicans (F89) mayasý. Sonuçlar antibiyotiklerle (Flukonazol, Vankomisin, Sefepim ve Levofloksasin) karþýlaþtýrýldý. Tüm bileþikler bakteri ve mayalara karþý aktivite gösterdi. Bileþiklerde en iyi aktivite C. Albicans için Cu(OAc)2.2H2O (31,25 µg/mL), L. monocytogens için 1 ve 7 (31,25), B. subtilis için tüm bileþikler (6 hariç) (7,60 µg/mL), E. Coli için 2 (31,25 µg/mL), S. aureus için 7 (15,60 µg/mL), E. Faecalis için 7 (15,60 µg/mL) ve P. aeruginoa için 3 (15,60 µg/mL) sahiptir.

Anahtar Kelimeler: 2-Aminopiridin, 2-Metoksi-5-sülfamoilbenzoik Asit, Tuz, Cu(II) Kompleksleri, Anti-mikrobiyal Aktivite

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