Synthesis, characterization, anti-microbial activity studies of 2-methoxy-5-sulfamoylbenzoic acid and 2-amino-5/6-picoline salts and their Cu(II) complexes

Yıl 2024, Cilt: 8 Sayı: 1, 1 - 14, 30.06.2024

Halil İlkimen Aysel Gülbandılar

https://doi.org/10.47137/usufedbid.1395005

Öz

Two new salts (1 and 2) obtained between 2-methoxy-5-sulfamoylbenzoic acid (Hsba) and 2-amino-X-picoline {X = 5 (2a5mp) and 6 (2a6mp)} and their Cu(II) complexes (3 and 4) have been obtained. The structures of the salts (1 and 2) were suggested by elemental analysis, NMR, FT-IR and UV-Vis, while the structures of Cu(II) complexes (3 and 4) were suggested by elemental analysis, AAS, UV-Vis and magnetic susceptibility techniques. While the acid:base ratio was 1:1 for 1 and 2 salts, the metal:acid:base ratio was 1:2:2 for 3 and 4. According to the results of spectroscopic analysis, the structures of 3 and 4 compounds were proposed as octahedral. Additionally, anti-microbial activities of free ligands, salts and complexes 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, 2 and 4 (31.25 µg/mL) for C. Albicans, Hsba and 3 (31.25 µg/mL) for L. monocytogens, 2a5mp (7.80 µg/mL) for B. subtilis, all compounds (except Hsba and 2) (62.50 µg/mL) for E. Coli, Hsba (31.25 µg/mL) for S. aureus, 1 (31.25 µg/mL) for E. Faecalis and Hsba and 3 (15.60 µg/mL) for P. aeruginoa have the best activity.

Anahtar Kelimeler

2-Aminopicoline, 2-methoxy-5-sulfamoylbenzoic acid, salt, Cu(II) complexes, anti-bacterial activity, anti-fungal activity

Proje Numarası

The authors accept the support provided by the Kütahya Dumlupinar University Research Fund (Grant No. 2019/12 and 2020/02).

2-Metoksi-5-sülfamoilbenzoik asit ve 2-amino-5/6-pikolin tuzları ve bunların Cu(II) komplekslerinin sentezi, karakterizasyonu, anti-mikrobiyal aktivite çalışmaları

Öz

2-Metoksi-5-sülfamoilbenzoik asit (Hsba) ve 2-amino-X-pikolin {X = 5 (2a5mp) ve 6 (2a6mp)} arasında elde edilen iki yeni tuz (1 ve 2) ve bunların Cu(II) kompleksleri (3 ve 4) elde edilmiştir. Tuzların (1 ve 2) yapıları element analizi, NMR, FT-IR ve UV-Vis ile önerilirken Cu(II) komplekslerinin (3 ve 4) yapıları element analizi, AAS, UV-Vis ve manyetik duyarlılık teknikleri ile önerilmiştir. Asit:baz oranı 1 ve 2 tuzları için 1:1 iken, metal:asit:baz oranı 3 ve 4 tuzları için 1:2:2 idi. Spektroskopik analiz sonuçlarına göre 3 ve 4 bileşiklerinin yapıları şöyleydi: oktahedral olarak önerilmiştir. Ayrıca serbest ligandların, tuzların ve komplekslerin anti-mikrobiyal aktiviteleri Pseudomonas aeruginosa (ATCC 27853), Staphylococcus aureus (NRRL B-767), Bacillus subtilis, Enterococcus faecalis (ATCC 29212), Escherichia coli (ATCC25922) ve Listeria monocytogenes'e karşı incelenmiştir. (ATCC 7644) bakterileri ve Candida albicans (F89) mayası. Sonuçlar antibiyotiklerle (Flukonazol, Vankomisin, Sefepim ve Levofloksasin) karşılaştırıldı. Tüm bileşikler bakteri ve mayalara karşı aktivite gösterdi. Bileşiklerde C. Albicans için Cu(OAc)2.2H2O, 2 ve 4 (31,25 µg/mL), L. monocytogens için Hsba ve 3 (31,25 µg/mL), B. subtilis için 2a5mp (7,80 µg/mL), E. Coli için tüm bileşikler (Hsba ve 2 hariç) (62,50 µg/mL), S. aureus için Hsba (31,25 µg/mL), E. Faecalis için Hsba ve 1 (31,25 µg/mL) ve P. aeruginoa için 3 (15,60 µg/mL) en iyi aktiviteye sahiptir.

Anahtar Kelimeler

2-Aminopikolin, 2-metoksi-5-sülfamoilbenzoik asit, tuz, Cu(II) kompleksleri, anti-bakteriyel aktivite, anti-fungal aktivite.

Proje Numarası

The authors accept the support provided by the Kütahya Dumlupinar University Research Fund (Grant No. 2019/12 and 2020/02).

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