Sülfanilamit İçeren Maleik Asit ile Aminopiridin Türevlerinin Proton Tuzlarının Sentezi ve Karakterizasyonu

Öz

Bu çalışmada önce literatürde bulunan yöntemle maleik anhidrit (mal) ile sülfanilamitin (sa) tepkimesinden sülfanilamit içeren maleik asit olan (E)-3-(4-sülfamoilfenilkarbamoil) akrilik asit (1) sentezlenmiştir. Daha sonra 1 ile 2-amino-6-metilpiridin (2), 2-amino-5-metilpiridin (3), 2-amino-4-metilpiridin (4) ve 3-aminopiridin (5) tepkimesinden proton transfer tuzları (6-9) elde edilmiştir. Elde edilen tuzların yapıları, elementel analiz, 1H ve 13C Nükleer Manyetik Rezonans Spektroskopisi (NMR), Fourier Dönüşümlü Kızılötesi Spektroskopisi (FT-IR) ve yük denkliği ile önerilmiştir. Bu analiz sonuçlarına göre tuzlarda asit:baz oranı 1:1 olarak bulunmuştur. Bu çalışmada, suda çözülebilen ve farklı aktivite özellikleri gösterebilecek kimyasal madde sentezi hedeflenmiştir.

Anahtar Kelimeler

• (E)-3-(4-sülfamoyilfenilkarbamoil)akrilik asit
• Aminopiridinler
• Proton Transfer Tuzu

Synthesis and Characterization of Proton Salts of Sulfanilamide Containing Maleic Acid and Aminopyridine Derivatives

Öz

In this study, maleic acid containing sulfanilamide (E)-3-(4-sulfamoylphenylcarbamoyl) acrylic acid (1) was synthesized from the reaction of maleic anhydride (mal) and sulfanilamide (sa) with the method found in the literature. Then, proton transfer salts (6-9) were obtained. The structures of the obtained salts were suggested by elemental analysis, 1H and 13C Nuclear Magnetic Resonance Spectroscopy (NMR), Fourier Transform Infrared Spectroscopy (FT- IR) and charge balance. According to the results of this analysis, the acid:base ratio of salts was found to be 1:1. In this study, it was aimed to synthesize chemical substances that can be dissolved in water and have different activity properties.

Anahtar Kelimeler

• (E)-3-(4-sulfamoylphenylcarbamoyl)acrylic acid
• Aminopyridines
• Proton Transfer Salt

Kaynakça

1. Macdonald, J.C., Dorrestein, P.C., Pilley, M.M., Foote, M.M., Lundburg, J.L., Henning, R.W., Schultz, A.J., & Manson, J.L. (2000). Design of layered crystalline materials using coordination chemistry and hydrogen bonds. Journal of the American Chemical Society, 122, 11692-11702. https://doi.org/10.1021/ja002102v
2. Aghabozorg, H., Sadrkhanlou, E., Shokrollahi, A., Ghaedi, M., & Shamsipur., M. (2009). Synthesis, characterization, crystal structures, and solution studies of Ni(II), Cu(II) and Zn(II) complexes obtained from pyridine-2,6-dicarboxylic acid and 2,9-dimethyl-1,10-phenanthroline. Journal of Iranian Chemical Society, 6(1), 55-70. https://doi.org/10.1007/BF0324650
3. Farrag, A.A.S., Ammar, Y.A., El-Sehemi, A.A.G., Thabet, H.K., Hassan, N.A.A., & Samy, A.K. (2011). Synthesis and pharmacological screening of novel sulfamoylphenylcarbamoylquinoxaline derivatives as anti-inflammatory, analgesic and antitumour agents. Journal of Chemical Research, 35(3), 163-166. https://doi.org/10.3184/174751911X12983997221326
4. Jain, B.C., Iyer, B.H., & Guha, P.C. (1945). Some N- and N-heterocyclic-acyl-sulfanilamides. Science and Culture, 11, 270-271.
5. Jain, B.C., Iyer, B.H., & Guha, P.C. (1947). Sulfanilamides. XIII. Reaction with dicarboxylic acids -N - and N -acyl and heterocyclic derivatives. Journal of the Indian Chemical Society, 24, 173-176.
6. Irani, R.J. (1945). A simple method of preparation of N -substituted disulfanilamido derivatives of some dibasic acids. Current Science, 14, 46-47.
7. Oktay, K., Kose, L.P., Sendil, Ki., Gultekin, M.S., Gulcin, I., & Supuran, C.T., (2016). The synthesis of (Z)-4-oxo-4-(arylamino)but-2-enoic acids derivatives and determination of their inhibition properties against human carbonic anhydrase I and II isoenzymes. Journal of Enzyme Inhibition and Medicinal Chemistry, 31(6), 939-945. https://doi.org/10.3109/14756366.2015.1071808
8. Martin, G.J., Balant, C.P., Avakian, S., & Beiler, J.M., (1954). Inhibition of carbonic anhydrase. Archives Internationales de Pharmacodynamie et de Therapie, 98, 284-287.

9. Delmar, G.S., & Macallum, E.N. N (Carboxyacyl)sulfanilamides. United States, US2576825 1951-11-27.
10. Vargha, L., (1939). The semiamides of p-aminobenzenesulfonamide formed with dicarboxylic acids. Magyar Biol. Kutatointezet Munkai, 11, 372-374.
11. Miller, E., Rock, H.J., & Moore, M.L., (1939). Substituted sulfanilamides. I. N -Acyl derivatives. Journal of the American Chemical Society, 61, 1198-1200.
12. Merz, H., Pfleiderer, G., & Wieland, T., (1965). Synthesis of S- or S-containing maleimides. Biochemische Zeitschrift, 342(1), 66-75.
13. Valee, J.P.S. Soluble derivatives of aminobenzenesulfonamides. France, FR1055834 1954-02-22.
14. Bergmann, F., & Haskelberg, L., (1941). Synthesis of lipophilic chemotherapeuticals. V. N-Acylsulfanilamides. Journal of the American Chemical Society, 63, 2243-2245.
15. Tahir, M.N., Khalid, M., Islam, A., Ali Mashhadi, S.M., & Braga, A.A.C. (2017). Facile synthesis, single crystal analysis, and computational studies of sulfanilamide derivatives. Journal of Molecular Structure, 1127, 766-776. https://doi.org/10.1016/j.molstruc.2016.08.032
16. Poth, E.J., & Ross, C.A., (1944). Rates of hydrolysis of N -dibasic acid-substituted sulfonamides. Proceedings of the Society for Experimental Biology and Medicine, 57, 322-327.
17. Ciba, J., Sycz, J., & Trzcionka, J. (1983), Study of the thermal properties of derivatives of sulfonamides. Journal of Thermal Analysis, 26(1), 145-150.
18. Ciba, J., & Trzcionka, J., (1983). Derivatives of sulfanilamide and dicarboxylic acids. Zeszyty Naukowe Politechniki Slaskiej, Chemia, 751(106), 107-116.
19. Bergmann, F., & Schapiro, D., (1942). Further acylation experiments with sulfanilamide and heterocyclic amines. Journal of Organic Chemistry, 7, 419-423.
20. Nigmatov, I.N., Gafurov, B.L., & Askarov, M.A., (1977), Study of the reaction of citraconic anhydride with p-aminobenzenesulfamide. Uzbekskii Khimicheskii Zhurnal, (3), 41-43.
21. Kremlev, M.M., Kul'chitskaya, N.E., Biba, A.D., & Romanenko, V.D., (1971). Arenesulfonamides. XXVII. N-(sulfamoylaryl)maleimides. Khimicheskaya Tekhnologiya (Kharkov), 21, 5-10.
22. Goya, H., Nakanishi, M., Saruwatori, K., Hirose, A., & Shinozawa, T., Sulfanilamides as inhibitors of oxidation of ammoniacal nitrogen in soils. Japan, JP47004966 B 1972-02-12.
23. Yenikaya, C., Ilkimen, H., Demirel, M.M., Ceyhan, B., Bulbul, M., & Tunca, E., (2016). Preparation of two maleic acid sulfonamide salts and their copper(II) complexes and antiglaucoma activity studies. Journal of the Brazilian Chemical Society, 27(10), 1706-1714. https://doi.org/10.5935/0103-5053.20160051
24. Bapna, S., Hiran, B.L., & Jain, S., (2015). Antimicrobial evaluation of maleimide monomers, homopolymers and copolymers containing azo, sulfonamide and thiazole groups. Journal of Advances in Chemistry, 11(1), 3404-3415. https://doi.org/10.24297/jac.v11i1.2228
25. Yenikaya, C., Ilkimen, H., Demirel, M.M., Ceyhan, B., Tunca, E., & Bulbul, M., (2016). 2-Aminopiridin ile (E)-4-okso-4-((4-sülfamoyilfenil)amino)büt-2-enoik asitin proton transfer tuzunun sentezi, metal komplekslerinin hazırlanması ve hCA I ve hCA II izoenzimleri üzerindeki inhibisyon özelliklerinin incelenmesi. Afyon Kocatepe Üniversitesi Fen ve Mühendislik Bilimleri Dergisi, 16, 41‐53.
26. Yenikaya, C., Ilkimen, H., Ceyhan, B., Demirel, M.M., Tunca, E., & Bulbul, M., (2017). Benzimidazol ile (E)-3-(4-sülfamoyilfenilkarbamoil)akrilik asitin proton transfer tuzunun sentezi, metal komplekslerinin hazırlanması ve inhibisyon özelliklerinin incelenmesi. Sakarya Üniversitesi Fen Bilimleri Dergisi, 21(3), 454-462.
27. Marinescu, M. (2017). 2-Aminopyridine-A classic and trendy pharmacophore. International Journal of Pharma and Bio Sciences, 8(2), 338-355. http://dx.doi.org/10.22376/ijpbs.2017.8.2.p338-355
28. Cook D. Vibrational spectra of pyridinium salts. Canadian Journal of Chemistry, 1961, 39, 2009–2024. https://doi.org/10.1139/[e-mail]01