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Sülfametiyazol-2,2′-Bipiridin Tuzunun Yapısal ve Spektral İncelenmesi: Deneysel ve Moleküler Modelleme Çalışması

Year 2020, Volume: 9 Issue: 2, 525 - 541, 15.06.2020
https://doi.org/10.17798/bitlisfen.596702

Abstract

Bu çalışmada Sülfametiyazol-2,2′-Bipiridin tuzunun
sentezi, spektroskopik özellikleri (IR, UV-Vis ve termal) açıklanmaktadır.
Birim hücrenin asimetrik biriminde, bir sülfametiyazol, bir 2,2′-Bipiridin
içermektedir. Karakterizasyon için tek kristal X-ışını kırınımı tekniği
kullanılmıştır. 296 K' de tek kristal X-ışını kırınımı sonucuna göre
P21/n monoklinik uzay grubunda a = 8.658 (3) Å, b =
24.686 (6) Å, c = 9.927 (4) Å, α = 90º, β = 103.61 (3)º, γ = 90º ve Z = 4 olarak
kristallendiği görülmüştür. Molekül üzerine kapsamlı olarak teorik ve deneysel
yapısal çalışmalar FT-IR ve UV-Vis spektroskopisi ile yapılmıştır. Teorik
hesaplamalar ve optimize edilmiş geometrik parametrelerin tümü, yoğunluk
fonksiyonel teorisi (DFT), B3LYP hibrit yöntemi 6-31G (d,p) baz seti
kullanılarak hesaplanmıştır. TGA ile termal özellikler incelenmiştir. Kompleksin
Staphylococcus aureus, Bacillus subtilis,
Escherichia coli,
Pseudomonas
aeruginosa,
Candida albicans ve Aspergillus flavus’a karşı
antimikrobiyal çalışmaları yapılmıştır. Optimize edilmiş kompleks, 5J9B, 5BMM,
5HTG, 1ZUV, 4F0V ve 4YNU’ya yerleştirilerek biyolojik aktivitesi teorik olarak
incelenmiştir.

References

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  • 2. Medina J.C., Roche D., Shan B., Learned R.M., Frankmoelle W.P., Clark D.L., Rosen T., Jaen J.C. 1999. Novel halogenated sulfonamides inhibit the growth of multidrug resistant MCF-7/ADR cancer cells, Bioorganic & medicinal chemistry letters, 9(13): 1843-1846.
  • 3. Northey E.H., Litchfield J.T., White H.J. 1948. Sulfonamides and allied compounds.
  • 4. Rall T., The Pharmacological Basis of Therapeutics. 8th edn.(Gilman, AG; Rall, TW; Nies, AS; Taylor, P. ed.). 1990, Perfamon Press. New York.
  • 5. Irvine A.D., Hoeger P.D.P.H., Yan A.C. 2011. Harper's Textbook of Pediatric Dermatology. Wiley.
  • 6. Bjerrum L., Dessau R.B., Hallas J. 2002. Treatment failures after antibiotic therapy of uncomplicated urinary tract infections. A prescription database study, Scandinavian journal of primary health care, 20(2): 97-101.
  • 7. Bjerrum L., Gahrn-Hansen B., Grinsted P. 2009. Pivmecillinam versus sulfamethizole for short-term treatment of uncomplicated acute cystitis in general practice: a randomized controlled trial, Scandinavian journal of primary health care, 27(1): 6-11.
  • 8. Suzuki T., Yamamoto Y., Abe K., Hirano M., Oka H. 1999. Sulfamethizole capsules containing contrast medium for assessment of gastric emptying in functional dyspepsia patients, Digestive diseases and sciences, 44(9): 1741-1746.
  • 9. Chourasiya S.S., Patel D.R., Nagaraja C., Chakraborti A.K., Bharatam P.V. 2017. Sulfonamide vs. sulfonimide: tautomerism and electronic structure analysis of N-heterocyclic arenesulfonamides, New Journal of Chemistry, 41(16): 8118-8129.
  • 10. Suresh K., Minkov V.S., Namila K.K., Derevyannikova E., Losev E., Nangia A., Boldyreva E.V. 2015. Novel synthons in sulfamethizole cocrystals: structure–property relations and solubility, Crystal Growth & Design, 15(7): 3498-3510.
  • 11. Duggirala N.K., Perry M.L., Almarsson Ö., Zaworotko M.J. 2016. Pharmaceutical cocrystals: along the path to improved medicines, Chemical Communications, 52(4): 640-655.
  • 12. Stoe C. 2002. X-AREA (Version 1.18) and X-RED (Version 1.04), Stoe & Cie, Darmstadt, Germany.
  • 13. Burla M.C., Camalli M., Carrozzini B., Cascarano G.L., Giacovazzo C., Polidori G., Spagna R. 1999. SIR99, a program for the automatic solution of small and large crystal structures, Acta Crystallographica Section A: Foundations of Crystallography, 55(6): 991-999.
  • 14. Sheldrick G.M. 2015. Crystal structure refinement with SHELXL, Acta Crystallogr C Struct Chem, 71(Pt 1): 3-8.
  • 15. Frisch M., Trucks G., Schlegel H.B., Scuseria G., Robb M., Cheeseman J., Scalmani G., Barone V., Mennucci B., Petersson G. 2009. Gaussian 09, revision a. 02, gaussian, Inc., Wallingford, CT, 200.
  • 16. Trott O., Olson A.J. 2010. AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading, Journal of computational chemistry, 31(2): 455-461.
  • 17. BIOVIA D.S., BIOVIA Discovery Studio Visualizer, v16. 1.0. 15350, San Diego: Dassault Systemes; 2015 [cited: 2017 Mar 20].
  • 18. Öztürk F., Bulut İ., Yavuz Y., Bulut A. 2016. Sulfamethizole–2-amino-4, 6-dimethoxypyrimidine (1/1), IUCrData, 1(6): x161030.
  • 19. Öztürk F., Bulut İ., Bulut A. 2015. Structural, spectroscopic, magnetic and electrochemical studies of monomer N-substituted-sulfanilamide copper (II) complex with 2, 2′-bipyridine, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 138: 891-899.
  • 20. Vega-Hissi E.G., Andrada M.F., Zamarbide G.N., Estrada M.R., Tomás-Vert F. 2011. Theoretical studies on sulfanilamide and derivatives with antibacterial activity: conformational and electronic analysis, Journal of molecular modeling, 17(6): 1317-1323.
  • 21. Das D., Sahu N., Roy S., Dutta P., Mondal S., Torres E.L., Sinha C. 2015. The crystal structure of sulfamethoxazole, interaction with DNA, DFT calculation, and molecular docking studies, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 137: 560-568.
  • 22. Merrick J.P., Moran D., Radom L. 2006. An Evaluation of Harmonic Vibrational Frequency Scale Factors, J. Phys. Chem. A 111: 11683-11700.
  • 23. Jarzqcki A.A., Kozlowski P.M., Pulay P., Ye B.H., Li X.Y. 1997. Scaled quantum mechanical and experimental vibrational spectra of magnesium and zinc porphyrins, Spectrochimic Acta Part A 53: 1195- 1209.
  • 24. Yamamoto L.M., Nunes J.H.B., Ribeiro M.A., da Costa Ferreira A.M., Lustri W.R., Corbi P.P. 2017. Copper (II) and silver (I) complexes with sulfamethizole: synthesis, spectroscopic characterization, ESI-QTOF mass spectrometric analysis, crystal structure and antibacterial activities, Polyhedron, 138: 168-176.
  • 25. Hossain G.G., Amoroso A., Banu A., Malik K. 2007. Syntheses and characterisation of mercury complexes of sulfadiazine, sulfamerazine and sulfamethazine, Polyhedron, 26(5): 967-974.
  • 26. Padmaja L., Amalanathan M., Ravikumar C., Joe I.H. 2009. NBO analysis and vibrational spectra of 2, 6-bis (p-methyl benzylidene cyclohexanone) using density functional theory, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 74(2): 349-356.
  • 27. Obayes H.R., Al-Amiery A.A., Alwan G.H., Abdullah T.A., Kadhum A.A.H., Mohamad A.B. 2017. Sulphonamides as corrosion inhibitor: Experimental and DFT studies, Journal of Molecular Structure, 1138: 27-34.
  • 28. O'boyle N.M., Tenderholt A.L., Langner K.M. 2008. Cclib: a library for package‐independent computational chemistry algorithms, Journal of computational chemistry, 29(5): 839-845.
  • 29. Polishchuk A.V., Karaseva E.T., Emelina T.B., Cramariuc O., Karasev V.E. 2011. Polymorphism and Intramolecular Proton Transfer in Fluoroquinolone Compounds, Journal of fluorescence, 21(6): 2117.
  • 30. Ayankojo A.G., Tretjakov A., Reut J., Boroznjak R., Öpik A., Rappich J., Furchner A., Karsten H., Syritski V. 2016. Molecularly Imprinted Polymer Integrated with a Surface Acoustic Wave Technique for Detection of Sulfamethizole Anal. Chem. 882: 1476-1484.
  • 31. Sayin K., Karakaş D., Kariper S.E., Sayin T.A. 2018. Computational study of some fluoroquinolones: Structural, spectral and docking investigations, Journal of Molecular Structure, 1156: 172-181.
Year 2020, Volume: 9 Issue: 2, 525 - 541, 15.06.2020
https://doi.org/10.17798/bitlisfen.596702

Abstract

References

  • 1. Toth J.E., Grindey G.B., Ehlhardt W.J., Ray J.E., Boder G.B., Bewley J.R., Klingerman K.K., Gates S.B., Rinzel S.M., Schultz R.M. 1997. Sulfonimidamide Analogs of Oncolytic Sulfonylureas, Journal of medicinal chemistry, 40(6): 1018-1025.
  • 2. Medina J.C., Roche D., Shan B., Learned R.M., Frankmoelle W.P., Clark D.L., Rosen T., Jaen J.C. 1999. Novel halogenated sulfonamides inhibit the growth of multidrug resistant MCF-7/ADR cancer cells, Bioorganic & medicinal chemistry letters, 9(13): 1843-1846.
  • 3. Northey E.H., Litchfield J.T., White H.J. 1948. Sulfonamides and allied compounds.
  • 4. Rall T., The Pharmacological Basis of Therapeutics. 8th edn.(Gilman, AG; Rall, TW; Nies, AS; Taylor, P. ed.). 1990, Perfamon Press. New York.
  • 5. Irvine A.D., Hoeger P.D.P.H., Yan A.C. 2011. Harper's Textbook of Pediatric Dermatology. Wiley.
  • 6. Bjerrum L., Dessau R.B., Hallas J. 2002. Treatment failures after antibiotic therapy of uncomplicated urinary tract infections. A prescription database study, Scandinavian journal of primary health care, 20(2): 97-101.
  • 7. Bjerrum L., Gahrn-Hansen B., Grinsted P. 2009. Pivmecillinam versus sulfamethizole for short-term treatment of uncomplicated acute cystitis in general practice: a randomized controlled trial, Scandinavian journal of primary health care, 27(1): 6-11.
  • 8. Suzuki T., Yamamoto Y., Abe K., Hirano M., Oka H. 1999. Sulfamethizole capsules containing contrast medium for assessment of gastric emptying in functional dyspepsia patients, Digestive diseases and sciences, 44(9): 1741-1746.
  • 9. Chourasiya S.S., Patel D.R., Nagaraja C., Chakraborti A.K., Bharatam P.V. 2017. Sulfonamide vs. sulfonimide: tautomerism and electronic structure analysis of N-heterocyclic arenesulfonamides, New Journal of Chemistry, 41(16): 8118-8129.
  • 10. Suresh K., Minkov V.S., Namila K.K., Derevyannikova E., Losev E., Nangia A., Boldyreva E.V. 2015. Novel synthons in sulfamethizole cocrystals: structure–property relations and solubility, Crystal Growth & Design, 15(7): 3498-3510.
  • 11. Duggirala N.K., Perry M.L., Almarsson Ö., Zaworotko M.J. 2016. Pharmaceutical cocrystals: along the path to improved medicines, Chemical Communications, 52(4): 640-655.
  • 12. Stoe C. 2002. X-AREA (Version 1.18) and X-RED (Version 1.04), Stoe & Cie, Darmstadt, Germany.
  • 13. Burla M.C., Camalli M., Carrozzini B., Cascarano G.L., Giacovazzo C., Polidori G., Spagna R. 1999. SIR99, a program for the automatic solution of small and large crystal structures, Acta Crystallographica Section A: Foundations of Crystallography, 55(6): 991-999.
  • 14. Sheldrick G.M. 2015. Crystal structure refinement with SHELXL, Acta Crystallogr C Struct Chem, 71(Pt 1): 3-8.
  • 15. Frisch M., Trucks G., Schlegel H.B., Scuseria G., Robb M., Cheeseman J., Scalmani G., Barone V., Mennucci B., Petersson G. 2009. Gaussian 09, revision a. 02, gaussian, Inc., Wallingford, CT, 200.
  • 16. Trott O., Olson A.J. 2010. AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading, Journal of computational chemistry, 31(2): 455-461.
  • 17. BIOVIA D.S., BIOVIA Discovery Studio Visualizer, v16. 1.0. 15350, San Diego: Dassault Systemes; 2015 [cited: 2017 Mar 20].
  • 18. Öztürk F., Bulut İ., Yavuz Y., Bulut A. 2016. Sulfamethizole–2-amino-4, 6-dimethoxypyrimidine (1/1), IUCrData, 1(6): x161030.
  • 19. Öztürk F., Bulut İ., Bulut A. 2015. Structural, spectroscopic, magnetic and electrochemical studies of monomer N-substituted-sulfanilamide copper (II) complex with 2, 2′-bipyridine, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 138: 891-899.
  • 20. Vega-Hissi E.G., Andrada M.F., Zamarbide G.N., Estrada M.R., Tomás-Vert F. 2011. Theoretical studies on sulfanilamide and derivatives with antibacterial activity: conformational and electronic analysis, Journal of molecular modeling, 17(6): 1317-1323.
  • 21. Das D., Sahu N., Roy S., Dutta P., Mondal S., Torres E.L., Sinha C. 2015. The crystal structure of sulfamethoxazole, interaction with DNA, DFT calculation, and molecular docking studies, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 137: 560-568.
  • 22. Merrick J.P., Moran D., Radom L. 2006. An Evaluation of Harmonic Vibrational Frequency Scale Factors, J. Phys. Chem. A 111: 11683-11700.
  • 23. Jarzqcki A.A., Kozlowski P.M., Pulay P., Ye B.H., Li X.Y. 1997. Scaled quantum mechanical and experimental vibrational spectra of magnesium and zinc porphyrins, Spectrochimic Acta Part A 53: 1195- 1209.
  • 24. Yamamoto L.M., Nunes J.H.B., Ribeiro M.A., da Costa Ferreira A.M., Lustri W.R., Corbi P.P. 2017. Copper (II) and silver (I) complexes with sulfamethizole: synthesis, spectroscopic characterization, ESI-QTOF mass spectrometric analysis, crystal structure and antibacterial activities, Polyhedron, 138: 168-176.
  • 25. Hossain G.G., Amoroso A., Banu A., Malik K. 2007. Syntheses and characterisation of mercury complexes of sulfadiazine, sulfamerazine and sulfamethazine, Polyhedron, 26(5): 967-974.
  • 26. Padmaja L., Amalanathan M., Ravikumar C., Joe I.H. 2009. NBO analysis and vibrational spectra of 2, 6-bis (p-methyl benzylidene cyclohexanone) using density functional theory, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 74(2): 349-356.
  • 27. Obayes H.R., Al-Amiery A.A., Alwan G.H., Abdullah T.A., Kadhum A.A.H., Mohamad A.B. 2017. Sulphonamides as corrosion inhibitor: Experimental and DFT studies, Journal of Molecular Structure, 1138: 27-34.
  • 28. O'boyle N.M., Tenderholt A.L., Langner K.M. 2008. Cclib: a library for package‐independent computational chemistry algorithms, Journal of computational chemistry, 29(5): 839-845.
  • 29. Polishchuk A.V., Karaseva E.T., Emelina T.B., Cramariuc O., Karasev V.E. 2011. Polymorphism and Intramolecular Proton Transfer in Fluoroquinolone Compounds, Journal of fluorescence, 21(6): 2117.
  • 30. Ayankojo A.G., Tretjakov A., Reut J., Boroznjak R., Öpik A., Rappich J., Furchner A., Karsten H., Syritski V. 2016. Molecularly Imprinted Polymer Integrated with a Surface Acoustic Wave Technique for Detection of Sulfamethizole Anal. Chem. 882: 1476-1484.
  • 31. Sayin K., Karakaş D., Kariper S.E., Sayin T.A. 2018. Computational study of some fluoroquinolones: Structural, spectral and docking investigations, Journal of Molecular Structure, 1156: 172-181.
There are 31 citations in total.

Details

Primary Language Turkish
Journal Section Araştırma Makalesi
Authors

Filiz Öztürk 0000-0002-0493-0446

Tuğba Aycan This is me

Ahmet Hilmi Çon 0000-0002-1225-0133

Publication Date June 15, 2020
Submission Date July 25, 2019
Acceptance Date March 22, 2020
Published in Issue Year 2020 Volume: 9 Issue: 2

Cite

IEEE F. Öztürk, T. Aycan, and A. H. Çon, “Sülfametiyazol-2,2′-Bipiridin Tuzunun Yapısal ve Spektral İncelenmesi: Deneysel ve Moleküler Modelleme Çalışması”, Bitlis Eren Üniversitesi Fen Bilimleri Dergisi, vol. 9, no. 2, pp. 525–541, 2020, doi: 10.17798/bitlisfen.596702.

Bitlis Eren University
Journal of Science Editor
Bitlis Eren University Graduate Institute
Bes Minare Mah. Ahmet Eren Bulvari, Merkez Kampus, 13000 BITLIS