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

Abstract

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

2-Metoksi-5-sülfamoilbenzoik asit ve 2-aminopiridin türevlerinin tuzları ve bunların Cu(II) komplekslerinin sentezi, karakterizasyonu, antimikrobiyal aktivite çalışmaları

Abstract

2-Metoksi-5-sülfamoilbenzoik asit (1) ve 2-aminopiridin (2) veya 2-amino-4-metilpiridin (3) reaksiyonundan iki yeni tuz (4 ve 5) ve bunların Cu(II) kompleksleri (6 ve 7) elde edildi. Tuzların (4 ve 5) yapıları element analizi, NMR, FT-IR ve UV-Vis ile aydınlatılırken, Cu(II) komplekslerinin (6 ve 7) yapıları element analizi, AAS, UV-Vis ve manyetik duyarlılık teknikleri ile önerildi. Asit:baz oranı 4 tuz için 2:1 ve 5 tuz için 1:1 iken, metal:asit:baz oranı 6 ve 7 için 1:2:2’dir. Spektroskopik analiz sonuçlarına göre 6 ve 7 bileşik oktahedral olarak önerildi. Ayrıca, tüm bileşiklerin 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) mayası. Sonuçlar antibiyotiklerle (Flukonazol, Vankomisin, Sefepim ve Levofloksasin) karşılaştırıldı. Tüm bileşikler bakteri ve mayalara karşı aktivite gösterdi. Bileşiklerde 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 bileşikler (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.

Keywords

• 2-Aminopiridin
• 2-Metoksi-5-sülfamoilbenzoik asit
• Tuz
• Cu(II) Kompleksleri
• Anti-Mikrobiyal aktivite

References

1. [1] Perrin DD, Dempsey B, Serjeant E. pKa Prediction for Organic Acids and Bases. 1nd ed. Dordrecht, Holland, Springer, 1981.
2. [2] Haynes DA, Jones W, Motherwell, WDS. “Occurrence of pharmaceutically acceptable anions and cations in the Cambridge Structural Database”. Journal of Pharmaceutical Sciences, 94, 2111-2120, 2005.
3. [3] Berge SM, Bighley LD, Monkhouse DC. “Pharmaceutical salts”. Journal of Pharmaceutical Sciences, 66, 1-19 1977.
4. [4] Serajuddin AT. “Salt formation to improve drug solubility”. Advanced Drug Delivery Reviews, 59, 603-616, 2007.
5. [5] Marinescu M. “2-aminopyridine-a classic and trendy pharmacophore”. International Journal of Biological Sciences, 8(2), 338-355, 2017.
6. [6] Yenikaya C, Büyükkıdan N, Sarı M, Keşli R, Ilkimen 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, 64(19), 3353-3365, 2011.
7. [7] 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, 28(16), 3526-3532, 2009.
8. [8] Hamor GH, Reavlin BL. “Anticonvulsants. 3. Alkyl esters of 4-bromo-2-sulfamoylbenzoic acid and 4-chloro-2-sulfamoylbenzoic acid”. Journal of Pharmaceutical Sciences, 56, 134-136, 1967.

9. [9] Scozzafava A, Owa T, Mastrolorenzo A, Supuran CT. “Anticancer and antiviral sulfonamides”. Current Medicinal Chemistry, 10, 925-953, 2003.
10. [10] Supuran CT, Casini A, Mastrolorenzo A, Scozzafava A. “COX-2 selective inhibitors, carbonic anhydrase inhibition and anticancer properties of sulfonamides belonging to this class of pharmacological agents”. Mini-Reviews in Medicinal Chemistry, 4(6), 625-632, 2004.
11. [11] Choan ZH, Hassan M, Khan MK, Supuran CT. “In-vitro antibacterial, antifungal and cytotoxic properties of sulfonamide-derived Schiff's bases and their metal complexes. Journal of Enzyme Inhibition and Medicinal Chemistry, 20, 183-188, 2005.
12. [12] 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 and Medicinal Chemistry, 18(2), 930-938, 2010.
13. [13] Kumar R, Bua S, Ram S, Prete SD, Capasso C, Supuran CT, Sharma PK. “Benzenesulfonamide bearing imidazothiadiazole and thiazolotriazole scaffolds as potent tumor associated human carbonic anhydrase IX and XII inhibitors”. Bioorganic and Medicinal Chemistry, 25, 1286-1293, 2017.
14. [14] 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, 18, 1941–1946, 2021.
15. [15] İlkimen H, Salün SG, Yenikaya C, “Synthesis and characterization of metal complexes of 2-methoxy-5-sulfamoylbenzoic acid”. SOCRATES 1st International Health, Engineering and Applied Sciences Congress, Ankara, Türkiye, 19-20 Haziran 2021.
16. [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, 38(1), 13-17, 2019.
17. [17] İlkimen H, Salün SG, Yenikaya C. “Synthesis and characterization of Fe(III) metal complexes of sulfamoylbenzoic acid derivatives”. Euroasia Journal of Mathematics-Engineering Natural & Medical Sciences, 8, 108-116, 2020.
18. [18] İlkimen H, Yenikaya C, Gülbandılar A. “Synthesis, characterization and investigation of antimicrobial properties of proton transfer salts and Cu(II) complexes of 2-methoxy-5-sulfamoylbenzoic acid and 2,3-diaminopyridine derivatives”. III. Baskent International Conference on Multidisciplinary Studies, Ankara, Türkiye, 23-25 Eylül 2022.
19. [19] İlkimen H, Yenikaya C, Gülbandılar A. “Synthesis, characterization and investigation of antimicrobial and antifungal activities of 2-methoxy-5-sulfamoylbenzoic acid and 2-aminonitropyridine derivatives”. 3rd International Conference on Innovative Academic Studies, Konya, Türkiye, 26-28 Eylül 2023.
20. [20] İlkimen H, Gülbandılar A. “Synthesis, characterization and investigation of antimicrobial and antifungal activities of proton transfer salts of 2-amino-5-substituepiridin derivatives and 2-methoxy-5-sulfamoylbenzoic acid”. 2nd International Conference on Contemporary Academic Research ICCAR 2023, Konya, Türkiye, 4-5 Kasım 2023.
21. [21] İlkimen H, Gülbandılar A. “Synthesis, characterization and investigation of antimicrobial and antifungal activities of proton transfer salts of 2-amino-6-substituepiridin derivatives and 2-methoxy-5-sulfamoylbenzoic acid”. 2nd International Conference on Contemporary Academic Research ICCAR 2023, Konya, Türkiye, 4-5 Kasım 2023.
22. [22] Cook D, “Vibrational spectra of pyridinium salts”. Canadian Journal of Chemistry, 39(10), 2009-2023, 1961.
23. [23] Nakamoto K. Infrared and Raman Spectra of Inorganic and Coordination Compounds. 5th ed. New York, USA, Wiley-Interscience,1997.
24. [24] Sancak K, Er M, Ünver Y, Yıldırım M, Değirmencioğlu I, “Cu(II), Ni(II) and Fe(II) complexes with a new substituted [1,2,4] triazole Schiff base derived from 4-amino-5-(thien-2-yl ethyl)-2,4-dihydro-3H-1,2,4-triazol-3-one and 2-hydroxy-1-naphthaldehyde: synthesis, characterization and a comparison of theoretical and experimental results by Ab inito calculation”. Transition Metal Chemistry, 32, 16-22, 2007.
25. [25] 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, 66(1), 28-36, 2007.
26. [26] 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, 96, 468-479, 2012.