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

Yıl 2022, , 57 - 70, 29.06.2022
https://doi.org/10.33484/sinopfbd.1069649

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.

Destekleyen Kurum

Kütahya Dumlupınar Üniversitesi

Proje Numarası

2013/36

Teşekkür

Bu çalışma, Kütahya Dumlupınar Üniversitesi Bilimsel Araştırma Projeleri Komisyon’unca, 2013/36 numaralı proje olarak desteklenmiştir. Bu katkılarından dolayı Kütahya Dumlupınar Üniversitesi Bilimsel Araştırma Projeleri Komisyonu’na teşekkür ederiz.

Kaynakça

  • 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
  • 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
  • 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
  • Jain, B.C., Iyer, B.H., & Guha, P.C. (1945). Some N- and N-heterocyclic-acyl-sulfanilamides. Science and Culture, 11, 270-271.
  • 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.
  • Irani, R.J. (1945). A simple method of preparation of N -substituted disulfanilamido derivatives of some dibasic acids. Current Science, 14, 46-47.
  • 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
  • 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.
  • Delmar, G.S., & Macallum, E.N. N (Carboxyacyl)sulfanilamides. United States, US2576825 1951-11-27.
  • Vargha, L., (1939). The semiamides of p-aminobenzenesulfonamide formed with dicarboxylic acids. Magyar Biol. Kutatointezet Munkai, 11, 372-374.
  • Miller, E., Rock, H.J., & Moore, M.L., (1939). Substituted sulfanilamides. I. N -Acyl derivatives. Journal of the American Chemical Society, 61, 1198-1200.
  • Merz, H., Pfleiderer, G., & Wieland, T., (1965). Synthesis of S- or S-containing maleimides. Biochemische Zeitschrift, 342(1), 66-75.
  • Valee, J.P.S. Soluble derivatives of aminobenzenesulfonamides. France, FR1055834 1954-02-22.
  • Bergmann, F., & Haskelberg, L., (1941). Synthesis of lipophilic chemotherapeuticals. V. N-Acylsulfanilamides. Journal of the American Chemical Society, 63, 2243-2245.
  • 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
  • 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.
  • Ciba, J., Sycz, J., & Trzcionka, J. (1983), Study of the thermal properties of derivatives of sulfonamides. Journal of Thermal Analysis, 26(1), 145-150.
  • Ciba, J., & Trzcionka, J., (1983). Derivatives of sulfanilamide and dicarboxylic acids. Zeszyty Naukowe Politechniki Slaskiej, Chemia, 751(106), 107-116.
  • Bergmann, F., & Schapiro, D., (1942). Further acylation experiments with sulfanilamide and heterocyclic amines. Journal of Organic Chemistry, 7, 419-423.
  • 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.
  • 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.
  • 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.
  • 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
  • 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
  • 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.
  • 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.
  • 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
  • Cook D. Vibrational spectra of pyridinium salts. Canadian Journal of Chemistry, 1961, 39, 2009–2024. https://doi.org/10.1139/v61-271@cjc-csc.issue01

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

Yıl 2022, , 57 - 70, 29.06.2022
https://doi.org/10.33484/sinopfbd.1069649

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.

Proje Numarası

2013/36

Kaynakça

  • 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
  • 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
  • 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
  • Jain, B.C., Iyer, B.H., & Guha, P.C. (1945). Some N- and N-heterocyclic-acyl-sulfanilamides. Science and Culture, 11, 270-271.
  • 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.
  • Irani, R.J. (1945). A simple method of preparation of N -substituted disulfanilamido derivatives of some dibasic acids. Current Science, 14, 46-47.
  • 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
  • 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.
  • Delmar, G.S., & Macallum, E.N. N (Carboxyacyl)sulfanilamides. United States, US2576825 1951-11-27.
  • Vargha, L., (1939). The semiamides of p-aminobenzenesulfonamide formed with dicarboxylic acids. Magyar Biol. Kutatointezet Munkai, 11, 372-374.
  • Miller, E., Rock, H.J., & Moore, M.L., (1939). Substituted sulfanilamides. I. N -Acyl derivatives. Journal of the American Chemical Society, 61, 1198-1200.
  • Merz, H., Pfleiderer, G., & Wieland, T., (1965). Synthesis of S- or S-containing maleimides. Biochemische Zeitschrift, 342(1), 66-75.
  • Valee, J.P.S. Soluble derivatives of aminobenzenesulfonamides. France, FR1055834 1954-02-22.
  • Bergmann, F., & Haskelberg, L., (1941). Synthesis of lipophilic chemotherapeuticals. V. N-Acylsulfanilamides. Journal of the American Chemical Society, 63, 2243-2245.
  • 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
  • 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.
  • Ciba, J., Sycz, J., & Trzcionka, J. (1983), Study of the thermal properties of derivatives of sulfonamides. Journal of Thermal Analysis, 26(1), 145-150.
  • Ciba, J., & Trzcionka, J., (1983). Derivatives of sulfanilamide and dicarboxylic acids. Zeszyty Naukowe Politechniki Slaskiej, Chemia, 751(106), 107-116.
  • Bergmann, F., & Schapiro, D., (1942). Further acylation experiments with sulfanilamide and heterocyclic amines. Journal of Organic Chemistry, 7, 419-423.
  • 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.
  • 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.
  • 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.
  • 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
  • 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
  • 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.
  • 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.
  • 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
  • Cook D. Vibrational spectra of pyridinium salts. Canadian Journal of Chemistry, 1961, 39, 2009–2024. https://doi.org/10.1139/v61-271@cjc-csc.issue01
Toplam 28 adet kaynakça vardır.

Ayrıntılar

Birincil Dil Türkçe
Konular Kimya Mühendisliği
Bölüm Araştırma Makaleleri
Yazarlar

Halil İlkimen 0000-0003-1747-159X

Cengiz Yenikaya 0000-0002-5867-9146

Proje Numarası 2013/36
Yayımlanma Tarihi 29 Haziran 2022
Gönderilme Tarihi 9 Şubat 2022
Yayımlandığı Sayı Yıl 2022

Kaynak Göster

APA İlkimen, H., & Yenikaya, C. (2022). Sülfanilamit İçeren Maleik Asit ile Aminopiridin Türevlerinin Proton Tuzlarının Sentezi ve Karakterizasyonu. Sinop Üniversitesi Fen Bilimleri Dergisi, 7(1), 57-70. https://doi.org/10.33484/sinopfbd.1069649


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