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2-Aminopiridin türevleri ile 2-metoksi-5-sülfamoyilbenzoik asit tuzlarının sentezi, karakterizasyonu, antimikrobiyal aktivitelerinin incelenmesi

Year 2023, Volume: 49 Issue: 2, 53 - 63, 30.10.2023

Halil İlkimen Cengiz Yenikaya Aysel Gülbandılar

https://doi.org/10.35238/sufefd.1315568

Abstract

Bu çalışmada, 2-metoksi-5-sülfamoyilbenzoik asit (Hsba) ile 2-aminopiridin (ap), 2-benzilaminopiridin (2Bzap), 2-aminometilpiridin (2amp) ve 2-amino-3-hidroksipiridin (2a3OHp)’in proton transfer tuzları (2apsba, 2Bzapsba, 2ampsba ve 2a3OHpsba) sentezlenmiştir. Başlangıç maddeleri ve proton transfer tuzlarının Enterococcus faecalis (ATCC 29212), Listeria monocytogenes (ATCC 7644), Bacillus subtilis, Staphylococcus aureus (NRRL-B 767) (Gram pozitif), Escherichia coli (ATCC 25922) ve Pseudomonas aeruginosa (ATCC 27853) (Gram negatif) bakterilerine ve Candida Albicans (ATCC 14053) mayasına karşı antibakteriyel ve antifungal aktiviteleri incelenmiştir. Antifungal aktiviteler Flukonazol ile antibakteriyel aktiviteleri ise Sefepim, Vankomisin ve Levofloksasin ile kıyaslanmıştır. Deneyde kullanılan ve sentezlenen bileşikler bakteri ve mayalara karşı aktiviteye sahiptir. Bileşiklerin en iyi aktivite değerleri B. subtilis bakterisinde 2Bzap ve 2a3OHp (31,25 µg/mL), E. faecalis ve S. aureus bakterilerinde tüm bileşikler (Hsba hariç) (62,50 µg/mL), E. coli bakterisinde 2a3OHpsba (15,60 µg/mL), L. monocytogenes bakterisinde Hsba, 2Bzap, 2amp ve 2a3OHp (31,25 µg/mL), P. aeruginoa bakterisinde Hsba (31,25 µg/mL) ve C. albicans mayasında 2Bzap (31,25 µg/mL)’de gözlenmiştir.

Keywords

2-Metoksi-5-sülfamoyilbenzoik asit 2-Aminopiridin Proton Transfer Tuzu Antifungal aktivite Antibakteriyel Aktivite

Supporting Institution

Kütahya Dumlupınar Üniversitesi

Project Number

2022/29

Thanks

Bu çalışma, Kütahya Dumlupınar Üniversitesi Bilimsel Araştırma Projeleri Komisyon’unca, 2022/29 numaralı proje olarak desteklenmiştir. Katkılarından dolayı Kütahya Dumlupınar Üniversitesi Bilimsel Araştırma Projeleri Komisyonu’na teşekkür ederiz.

References

  • Avan, İ., Güven, A., Güven K. 2013, Synthesis and antimicrobial investigation of some 5H-pyridazino[4,5-b]indoles. Turkish Journal of Chemistry, 37: 271-291.
  • Berge, S. M., Bighley, L. D., Monkhouse, D. C., 1977, Pharmaceutical salts. Journal of Pharmaceutical Sciences, 66, 1-19.
  • Choan, Z. H., Hassan, M., Khan, M. K., Supuran, C. T., 2005, 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.
  • Fuhrmann, H., Brenner, S., Arndt, P., Kempe, R., 1996, Octahedral group 4 metal complexes that contain amine, amido, and aminopyridinato ligands: synthesis, structure, and application in α-olefin oligo- and polymerization, Inorganic Chemistry, 35, 6742-6745.
  • Hamor, G. H., Reavlin, B. L., 1967, Anticonvulsants III: Alkyl esters of 4-bromo-2-sulfamoylbenzoic acid and 4-chloro-2-sulfamoylbenzoic acid. Journal of Pharmaceutical Sciences, 56, 134-136.
  • Haynes, D. A., Jones, W., Motherwell, W. D. S., 2005, Occurrence of pharmaceutically acceptable anions and cations in the Cambridge Structural Database. Journal of Pharmaceutical Sciences, 94, 2111-2120.
  • İlkimen, H., 2019, 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.
  • İlkimen, H., Salün, S. G., Yenikaya, C. 2-Metoksi-5-sülfamoyilbenzoik asitin metal komplekslerinin sentezi ve karakterizasyonu. SOCRATES 1st International Health, Engineering and Applied Sciences Congress. 19-20 Haziran 2021b, Ankara, Türkiye.
  • İlkimen, H., Salün, S. G., Yenikaya, C., 2020, Sülfamoyilbenzoik asit türevlerinin Fe(III) metal komplekslerinin sentezi ve karakterizasyonu. Euroasia Journal Of Mathematics-Engineering Natural, Medical Sciences, 8, 108-116.
  • İlkimen, H., Türken, N., Gülbandılar, A., 2021a, 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.
  • 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.
  • III. Baskent International Conference On Multidisciplinary Studies, September 23-25, 2022, Ankara, Türkiye.
  • Kaplancıklı, Z.A., Turan-Zitouni, G., Özdemir, A., Güven, K., 2004, Synthesis and study of antibacterial and antifungal activitiesof novel 2-[[(benzoxazole/ benzimidazole2yl)sulfanyl] acetylamino]thiazoles. Archives of Pharmacal Research, 27(11), 1081-1085.
  • Kaplancıklı, Z.A., Turan-Zitouni, G., Özdemir, A., Revial, G., Güven, K., 2007, Synthesis and antimicrobial activity of some thiazolyl-pyrazoline derivatives. Phosphorus, Sulfur, and Silicon and the Related Elements, 182(4), 749-764.
  • Kumar, R., Bua, S., Ram, S., Prete, S. D., Capasso, C., Supuran, C. T., Sharma, P. K., 2017, Benzenesulfonamide bearing imidazothiadiazole and thiazolotriazole scaffolds as potent tumor associated human carbonic anhydrase IX and XII in-hibitors. Bioorganic, Medicinal Chemistry, 25, 1286-1293.
  • Lim, C., Bashford, D., Karplus, M. 1991, Absolute pKa calculations with continuum dielectric methods. The Journal of Physical Chemistry, 95, 5610–5620
  • Manchester, J., Walkup, G., Rivin O., You, Z. 2010, Evaluation of pKa estimation methods on 211 druglike compounds. Journal of Chemical Information and Modeling, 50, 565–571.
  • Marinescu, M., 2017, 2-aminopyridine – a classic and trendy pharmacophore. International Journal of Pharma and Bio Sciences, 8(2), 338-355
  • Mistri, S., Zangrando, E., Manna, S. C., 2013, Cu(II) complexes of pyridine-2,6-dicarboxylate and N-donor neutral lig-ands: Synthesis, crystal structure, thermal behavior, DFT calculation and effect of aromatic compounds on their fluorescence, Inorganica Chimica Acta, 405, 331–338.
  • Perrin, D. D., Dempsey, B., Serjeant, E. P., 1981, pKa prediction for organic acids and bases. Springer.
  • Raso, A. G., Fiol, J. J., Zafra, A. L., Cabrero, A., Mata, I. Molins, E., 1999, Crystal structures of the N-salicylidene–L-serinatoaquacopper(II) monohydrate and its ternary de-rivative with 2-aminopyridine. Polyhedron, 18, 871–878.
  • Scozzafava, A., Owa, T., Mastrolorenzo, A., Supuran, C. T., 2003, Anticancer and antiviral sulfonamides. Current Medicinal Chemistry, 10, 925-953.
  • Serajuddin, A. T., 2007, Salt formation to improve drug solubility. Advanced Drug Delivery Reviews, 59, 603-616.
  • Supuran, C. T., Casini, A., Mastrolorenzo, A., Scozzafava, A., 2004, 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, 625-632.
  • Yenikaya, C., Büyükkıdan, N., Sarı, M., Keşli, R., İlkimen, H., Bülbül, M., Büyükgüngör, O. 2011, Synthesis, characterization, and biological evaluation of Cu(II) complexes with the pro-ton transfer salt of 2,6-pyridinedicarboxylic acid and 2-amino-4-methylpyridine. Journal of Coordination Chemistry, 64, 3353–3365.
  • Yenikaya, C., Poyraz, M., Sarı, M., Demirci, F., İlkimen, H. Büyükgüngör, O., 2009, Synthesis, characterization and biological evaluation of a novel Cu(II) complex with the mixed lig-ands 2,6-pyridinedicarboxylic acid and 2-aminopyridine. Polyhedron, 28, 3526-3532.
  • Yenikaya, C., Sarı, M., Bülbül, M., İlkimen, H., Çelik, H., Büyükgüngör, O., 2010, Synthesis, characterization and antiglaucoma activity of a novel proton transfer compound and a mixed-ligand Zn(II) complex. Bioorganic, Medicinal Chemistry, 18, 930-938.

Synthesis, characterization and investigation of antimicrobial activities of salts of 2-aminopyridine derivatives and 2-methoxy-5-sulfamoylbenzoic acid

Year 2023, Volume: 49 Issue: 2, 53 - 63, 30.10.2023

Halil İlkimen Cengiz Yenikaya Aysel Gülbandılar

https://doi.org/10.35238/sufefd.1315568

Abstract

In this study, proton transfer salts (2apsba, 2Bzapsba, 2ampsba and 2a3OHpsba) between 2-methoxy-5-sulfamoylbenzoic acid (Hsba) and 2-aminopyridine (ap), 2-benzylaminopyridine (2Bzap), 2-aminomethylpyridine (2amp) and 2-amino-3-hydroxypyridine (2a3OHp) were synthesized. Starting materials and proton transfer salts of Enterococcus faecalis (ATCC 29212), Listeria monocytogenes (ATCC 7644), Bacillus subtilis, Staphylococcus aureus (NRRL-B 767) (Gram positive), Escherichia coli (ATCC 25922) and Pseudomonas aeruginosa (ATCC 27853) (Gram negative) bacteria and Candida Albicans (ATCC 14053) yeast of antibacterial and antifungal activities against were investigated. Antifungal activities were compared with Fluconazole and antibacterial activities with Cefepime, Vancomycin and Levofloxacin. The compounds used and synthesized in the experiment have activity against bacteria and yeasts. The best activity values of the compounds were observed 2Bzap and 2a3OHp (31.25 µg/mL) in B. subtilis bacteria, all compounds (except Hsba) (62.50 µg/mL) in E. faecalis and S. aureus bacteria, 2a3OHpsba (15.60 µg/mL) in E. coli bacteria, 2Bzapsba, Hsba, 2Bzap, 2amp and 2a3OHp (31.25 µg/mL) in L. monocytogenes bacteria, Hsba (31.25 µg/mL) in P. aeruginoa bacteria and 2Bzap (31.25 µg/mL) in C. albicans yeast.

Keywords

2-Methoxy-5-sulfamoylbenzoic acid 2-Aminopyridine Proton Transfer Salt Antifungal activity Antibacterial activity.

Project Number

2022/29

References

  • Avan, İ., Güven, A., Güven K. 2013, Synthesis and antimicrobial investigation of some 5H-pyridazino[4,5-b]indoles. Turkish Journal of Chemistry, 37: 271-291.
  • Berge, S. M., Bighley, L. D., Monkhouse, D. C., 1977, Pharmaceutical salts. Journal of Pharmaceutical Sciences, 66, 1-19.
  • Choan, Z. H., Hassan, M., Khan, M. K., Supuran, C. T., 2005, 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.
  • Fuhrmann, H., Brenner, S., Arndt, P., Kempe, R., 1996, Octahedral group 4 metal complexes that contain amine, amido, and aminopyridinato ligands: synthesis, structure, and application in α-olefin oligo- and polymerization, Inorganic Chemistry, 35, 6742-6745.
  • Hamor, G. H., Reavlin, B. L., 1967, Anticonvulsants III: Alkyl esters of 4-bromo-2-sulfamoylbenzoic acid and 4-chloro-2-sulfamoylbenzoic acid. Journal of Pharmaceutical Sciences, 56, 134-136.
  • Haynes, D. A., Jones, W., Motherwell, W. D. S., 2005, Occurrence of pharmaceutically acceptable anions and cations in the Cambridge Structural Database. Journal of Pharmaceutical Sciences, 94, 2111-2120.
  • İlkimen, H., 2019, 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.
  • İlkimen, H., Salün, S. G., Yenikaya, C. 2-Metoksi-5-sülfamoyilbenzoik asitin metal komplekslerinin sentezi ve karakterizasyonu. SOCRATES 1st International Health, Engineering and Applied Sciences Congress. 19-20 Haziran 2021b, Ankara, Türkiye.
  • İlkimen, H., Salün, S. G., Yenikaya, C., 2020, Sülfamoyilbenzoik asit türevlerinin Fe(III) metal komplekslerinin sentezi ve karakterizasyonu. Euroasia Journal Of Mathematics-Engineering Natural, Medical Sciences, 8, 108-116.
  • İlkimen, H., Türken, N., Gülbandılar, A., 2021a, 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.
  • 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.
  • III. Baskent International Conference On Multidisciplinary Studies, September 23-25, 2022, Ankara, Türkiye.
  • Kaplancıklı, Z.A., Turan-Zitouni, G., Özdemir, A., Güven, K., 2004, Synthesis and study of antibacterial and antifungal activitiesof novel 2-[[(benzoxazole/ benzimidazole2yl)sulfanyl] acetylamino]thiazoles. Archives of Pharmacal Research, 27(11), 1081-1085.
  • Kaplancıklı, Z.A., Turan-Zitouni, G., Özdemir, A., Revial, G., Güven, K., 2007, Synthesis and antimicrobial activity of some thiazolyl-pyrazoline derivatives. Phosphorus, Sulfur, and Silicon and the Related Elements, 182(4), 749-764.
  • Kumar, R., Bua, S., Ram, S., Prete, S. D., Capasso, C., Supuran, C. T., Sharma, P. K., 2017, Benzenesulfonamide bearing imidazothiadiazole and thiazolotriazole scaffolds as potent tumor associated human carbonic anhydrase IX and XII in-hibitors. Bioorganic, Medicinal Chemistry, 25, 1286-1293.
  • Lim, C., Bashford, D., Karplus, M. 1991, Absolute pKa calculations with continuum dielectric methods. The Journal of Physical Chemistry, 95, 5610–5620
  • Manchester, J., Walkup, G., Rivin O., You, Z. 2010, Evaluation of pKa estimation methods on 211 druglike compounds. Journal of Chemical Information and Modeling, 50, 565–571.
  • Marinescu, M., 2017, 2-aminopyridine – a classic and trendy pharmacophore. International Journal of Pharma and Bio Sciences, 8(2), 338-355
  • Mistri, S., Zangrando, E., Manna, S. C., 2013, Cu(II) complexes of pyridine-2,6-dicarboxylate and N-donor neutral lig-ands: Synthesis, crystal structure, thermal behavior, DFT calculation and effect of aromatic compounds on their fluorescence, Inorganica Chimica Acta, 405, 331–338.
  • Perrin, D. D., Dempsey, B., Serjeant, E. P., 1981, pKa prediction for organic acids and bases. Springer.
  • Raso, A. G., Fiol, J. J., Zafra, A. L., Cabrero, A., Mata, I. Molins, E., 1999, Crystal structures of the N-salicylidene–L-serinatoaquacopper(II) monohydrate and its ternary de-rivative with 2-aminopyridine. Polyhedron, 18, 871–878.
  • Scozzafava, A., Owa, T., Mastrolorenzo, A., Supuran, C. T., 2003, Anticancer and antiviral sulfonamides. Current Medicinal Chemistry, 10, 925-953.
  • Serajuddin, A. T., 2007, Salt formation to improve drug solubility. Advanced Drug Delivery Reviews, 59, 603-616.
  • Supuran, C. T., Casini, A., Mastrolorenzo, A., Scozzafava, A., 2004, 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, 625-632.
  • Yenikaya, C., Büyükkıdan, N., Sarı, M., Keşli, R., İlkimen, H., Bülbül, M., Büyükgüngör, O. 2011, Synthesis, characterization, and biological evaluation of Cu(II) complexes with the pro-ton transfer salt of 2,6-pyridinedicarboxylic acid and 2-amino-4-methylpyridine. Journal of Coordination Chemistry, 64, 3353–3365.
  • Yenikaya, C., Poyraz, M., Sarı, M., Demirci, F., İlkimen, H. Büyükgüngör, O., 2009, Synthesis, characterization and biological evaluation of a novel Cu(II) complex with the mixed lig-ands 2,6-pyridinedicarboxylic acid and 2-aminopyridine. Polyhedron, 28, 3526-3532.
  • Yenikaya, C., Sarı, M., Bülbül, M., İlkimen, H., Çelik, H., Büyükgüngör, O., 2010, Synthesis, characterization and antiglaucoma activity of a novel proton transfer compound and a mixed-ligand Zn(II) complex. Bioorganic, Medicinal Chemistry, 18, 930-938.
There are 27 citations in total.

Details

Primary Language Turkish
Subjects Bioinorganic Chemistry, Transition Metal Chemistry
Journal Section Research Articles
Authors

Halil İlkimen 0000-0003-1747-159X

Cengiz Yenikaya 0000-0002-5867-9146

Aysel Gülbandılar 0000-0001-9075-9923

Project Number 2022/29
Publication Date October 30, 2023
Submission Date June 16, 2023
Published in Issue Year 2023 Volume: 49 Issue: 2

Cite

APA İlkimen, H., Yenikaya, C., & Gülbandılar, A. (2023). 2-Aminopiridin türevleri ile 2-metoksi-5-sülfamoyilbenzoik asit tuzlarının sentezi, karakterizasyonu, antimikrobiyal aktivitelerinin incelenmesi. Selçuk Üniversitesi Fen Fakültesi Fen Dergisi, 49(2), 53-63. https://doi.org/10.35238/sufefd.1315568
AMA İlkimen H, Yenikaya C, Gülbandılar A. 2-Aminopiridin türevleri ile 2-metoksi-5-sülfamoyilbenzoik asit tuzlarının sentezi, karakterizasyonu, antimikrobiyal aktivitelerinin incelenmesi. sufefd. October 2023;49(2):53-63. doi:10.35238/sufefd.1315568
Chicago İlkimen, Halil, Cengiz Yenikaya, and Aysel Gülbandılar. “2-Aminopiridin türevleri Ile 2-Metoksi-5-sülfamoyilbenzoik Asit tuzlarının Sentezi, Karakterizasyonu, Antimikrobiyal Aktivitelerinin Incelenmesi”. Selçuk Üniversitesi Fen Fakültesi Fen Dergisi 49, no. 2 (October 2023): 53-63. https://doi.org/10.35238/sufefd.1315568.
EndNote İlkimen H, Yenikaya C, Gülbandılar A (October 1, 2023) 2-Aminopiridin türevleri ile 2-metoksi-5-sülfamoyilbenzoik asit tuzlarının sentezi, karakterizasyonu, antimikrobiyal aktivitelerinin incelenmesi. Selçuk Üniversitesi Fen Fakültesi Fen Dergisi 49 2 53–63.
IEEE H. İlkimen, C. Yenikaya, and A. Gülbandılar, “2-Aminopiridin türevleri ile 2-metoksi-5-sülfamoyilbenzoik asit tuzlarının sentezi, karakterizasyonu, antimikrobiyal aktivitelerinin incelenmesi”, sufefd, vol. 49, no. 2, pp. 53–63, 2023, doi: 10.35238/sufefd.1315568.
ISNAD İlkimen, Halil et al. “2-Aminopiridin türevleri Ile 2-Metoksi-5-sülfamoyilbenzoik Asit tuzlarının Sentezi, Karakterizasyonu, Antimikrobiyal Aktivitelerinin Incelenmesi”. Selçuk Üniversitesi Fen Fakültesi Fen Dergisi 49/2 (October 2023), 53-63. https://doi.org/10.35238/sufefd.1315568.
JAMA İlkimen H, Yenikaya C, Gülbandılar A. 2-Aminopiridin türevleri ile 2-metoksi-5-sülfamoyilbenzoik asit tuzlarının sentezi, karakterizasyonu, antimikrobiyal aktivitelerinin incelenmesi. sufefd. 2023;49:53–63.
MLA İlkimen, Halil et al. “2-Aminopiridin türevleri Ile 2-Metoksi-5-sülfamoyilbenzoik Asit tuzlarının Sentezi, Karakterizasyonu, Antimikrobiyal Aktivitelerinin Incelenmesi”. Selçuk Üniversitesi Fen Fakültesi Fen Dergisi, vol. 49, no. 2, 2023, pp. 53-63, doi:10.35238/sufefd.1315568.
Vancouver İlkimen H, Yenikaya C, Gülbandılar A. 2-Aminopiridin türevleri ile 2-metoksi-5-sülfamoyilbenzoik asit tuzlarının sentezi, karakterizasyonu, antimikrobiyal aktivitelerinin incelenmesi. sufefd. 2023;49(2):53-6.
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