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Synthesis, Spectroscopic and Theoretical Characterization of Chiral Benzimidazole-Based Schiff Bases

Yıl 2026, Cilt: 9 Sayı: 1, 192 - 205, 15.01.2026
https://doi.org/10.34248/bsengineering.1776780
https://izlik.org/JA45NF56KE

Öz

Schiff bases are versatile compounds widely utilized in organic chemistry, serving as essential intermediates, starting materials, ligands, and catalysts. Their increasing significance in both practical applications and biological studies, particularly the notable bioactivity of their transition metal complexes, has sparked extensive scientific interest. In this context, the present study focuses on synthesizing novel chiral Schiff bases derived from benzimidazole, utilizing natural chiral amino acids as starting points. The condensation of these precursors with 4-(dimethylamino)benzaldehyde yielded four new Schiff base derivatives. To further investigate their potential biological activity, molecular docking studies were performed to examine the binding interactions between the synthesized compounds and selected target proteins. The results indicated that some derivatives showed high binding affinity, implying potential inhibitory activity. These findings highlight the promising pharmacological relevance of the synthesized compounds and support their future exploration in drug discovery research. Moreover, their coordination ability suggests potential applications as ligands in transition metal complexation.

Etik Beyan

No ethics committee approval was obtained for this research as no studies were conducted on animals or humans.

Destekleyen Kurum

Kırşehir Ahi Evran University

Proje Numarası

MMF.A4.23.007

Teşekkür

I would like to thank the Scientific Research Projects Coordination Unit of Kırşehir Ahi Evran University for supporting this study under the project number MMF.A4.23.007. Additionally, I would like to express my deep gratitude to Assoc. Prof. Tuncay Karakurt for his invaluable help and contributions to the theoretical calculations of this research.

Kaynakça

  • Ashraf, M., Wajid, A., Mahmood, K., Maah, M. J., & Yusoff, I. B. (2011). Spectral investigation of the activities of amino substituted bases. Oriental Journal of Chemistry, 27(1), 363–372.
  • Asif, M. (2019). Green synthesis of benzimidazole derivatives: an overview on green chemistry and its applications. Chemical Methodology, 3(6), 620–631. https://doi.org/10.33945/SAMI/CHEMM.2019.6.1
  • Aydınlı, E. A. (2006). Antimicrobial effects of some Schiff bases (Yüksek lisans tezi, Ankara Üniversitesi, Fen Bilimleri Enstitüsü).
  • Becke, A. D. (1993). Density‐functional thermochemistry. III. The role of exact exchange. The Journal of Chemical Physics, 98(7), 5648–5652.
  • Chang, Y. S. (2012). Hypersensitivity reactions to proton pump inhibitors. Current Opinion in Allergy and Clinical Immunology, 12(4), 348–353.
  • Dallakyan, S., & Olson, A. J. (2015). Small-molecule library screening by docking with PyRx. In J. Hempel, C. Williams, & C. Hong (Eds.), Chemical Biology Methods in Molecular Biology (Vol. 1263, pp. 243–250). Humana Press. https://doi.org/10.1007/978-1-4939-2269-7_19
  • Dennington, R., Keith, T., & Millam, J. (2009). GaussView, version 5. Semichem Inc.
  • DiRisio, R. J., Armstrong, J. E., Frank, M. A., Lake, W. R., & McNamara, W. R. (2017). Cobalt Schiff-base complexes for electrocatalytic hydrogen generation. Dalton Transactions, 46(32), 10418–10425.
  • Emregül, K. C., Düzgün, E., & Atakol, O. (2006). The application of some polydentate Schiff base compounds containing aminic nitrogens as corrosion inhibitors for mild steel in acidic media. Corrosion Science, 48(10), 3243–3260.
  • Foresman, J. B., & Frisch, A. (1996). Exploring chemistry with electronic structure methods: a guide to using Gaussian (2nd ed.). Gaussian Inc.
  • Frisch M, Trucks G, Schlegel HB, Scuseria G, Robb M, Cheeseman J, Scalmani G, Barone V, Mennucci B, Petersson G. 2009. Gaussian 09, revision A.02, Gaussian Inc, Wallingford, CT, USA, pp: 200.
  • Golcu, A., Tümer, M., Demirelli, H., & Wheatley, R. (2005). Cd(II) and Cu(II) complexes of polydentate Schiff base ligands: synthesis, characterization, properties and biological activity. Inorganica Chimica Acta, 358(6), 1785–1797.
  • Iwamoto, K., Uehara, Y., Inoue, Y., Taguchi, K., Muraoka, D., Ogo, N., Matsuno, K., & Asai, A. (2017). Inhibition of STAT3 by anticancer drug bendamustine. PLoS One, 12(1), Article e0169123.
  • Lasri, J., Elsherbiny, A. S., Eltayeb, N. E., Haukka, M., & El-Hefnawy, M. E. (2018). Synthesis and characterization of ferrocene-based Schiff base and ferrocenecarboxaldehyde oxime and their adsorptive removal of methyl blue from aqueous solution. Journal of Organometallic Chemistry, 866, 21–26.
  • Lee, C., Yang, W., & Parr, R. G. (1988). Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Physical Review B, 37(2), 785–789.
  • Lieberman, L. A., & Higgins, D. E. (2009). A small molecule screen identifies the antipsychotic drug pimozide as an inhibitor of Listeria monocytogenes infection. Antimicrobial Agents and Chemotherapy, 53(2), 756–764.
  • Pfeiffer, P., Breith, E., Lübbe, E., & Tsumaki, T. (1932). Thcylische orthokondesierte Nebenvalenzringe. Annalen der Chemie, 492(1), 81–127.
  • Politzer, P., Concha, M. C., & Murray, J. S. (2000). Density functional study of dimers of dimethylnitramine. International Journal of Quantum Chemistry, 80(2), 184–192.
  • Redshaw, C. (2017). Use of Metal Catalysts Bearing Schiff Base Macrocycles for the Ring Opening Polymerization (ROP) of Cyclic Esters. Catalysts, 7(5), 165.
  • Rehman, W., Baloch, M. K., Muhammad, B., Badshah, A., & Khan, K. M. (2004). Characteristic spectral studies and in vitro antifungal activity of some Schiff bases and their organotin (IV) complexes. Chinese Science Bulletin, 49(2), 119–122.
  • Schiff, H. (1869). Untersuchungen Uber Salicin Derivate. European Journal of Organic Chemistry, 150(3), 193–200.
  • Silva da, C. M., Silva da, D. L., Modolo, L. V., & Alves, R. B. (2011). Schiff bases: a short review of their antimicrobial activities. Journal of Advanced Research, 2(1), 1–8.
  • Upadhyay, K. K., Kumar, A., Upadhyay, S., & Mishra, P. C. (2008). Synthesis, characterization, structural optimization using density functional theory and superoxide ion scavenging activity of some Schiff bases. Journal of Molecular Structure, 873(1–3), 5–16.
  • Vigato, P. A., & Tamburini, S. (2004). The Challenge of Cyclic and Acyclic Schiff Bases and Related Derivatives. Coordination Chemistry Reviews, 248(17–20), 1717–2128.
  • Yeap, G. Y., Ha, S. T., Ishizawa, N., Suda, K., Boey, P. L., & Mahmood, W. A. K. (2003). Synthesis, crystal structure and spectroscopic study of para substituted 2-hydroxy-3- methoxybenzalideneanilines. Journal of Molecular Structure, 658(1–3), 87–99.
  • Zeishen, W., Zigi, G., & Zhenhuan, Y. (1990). Synthesis, characterization and anticanser activity of L-alanine Schiff base complexes of copper(II), zinc(II), and cobalt (II). Synthetic Reactivity in Inorganic and Metal-Organic Chemistry, 20(3), 335–344.
  • Zhang, J., Xu, L., & Wong, W. Y. (2018). Energy materials based on metal Schiff base complexes. Coordination Chemistry Reviews, 355, 180–198.
  • Zhang, P., Wang, H., Sun, L., Zhang, J., Xi, Y., Wu, Y., Yan, L. L., Li, X., & Sun, N. (2017). Telmisartan and hydrochlorothiazide antihypertensive treatmentin high sodium intake population: A randomized double blind trial. Journal of Hypertension, 35(10), 2077–2085.

Synthesis, Spectroscopic and Theoretical Characterization of Chiral Benzimidazole-Based Schiff Bases

Yıl 2026, Cilt: 9 Sayı: 1, 192 - 205, 15.01.2026
https://doi.org/10.34248/bsengineering.1776780
https://izlik.org/JA45NF56KE

Öz

Schiff bases are versatile compounds widely utilized in organic chemistry, serving as essential intermediates, starting materials, ligands, and catalysts. Their increasing significance in both practical applications and biological studies, particularly the notable bioactivity of their transition metal complexes, has sparked extensive scientific interest. In this context, the present study focuses on synthesizing novel chiral Schiff bases derived from benzimidazole, utilizing natural chiral amino acids as starting points. The condensation of these precursors with 4-(dimethylamino)benzaldehyde yielded four new Schiff base derivatives. To further investigate their potential biological activity, molecular docking studies were performed to examine the binding interactions between the synthesized compounds and selected target proteins. The results indicated that some derivatives showed high binding affinity, implying potential inhibitory activity. These findings highlight the promising pharmacological relevance of the synthesized compounds and support their future exploration in drug discovery research. Moreover, their coordination ability suggests potential applications as ligands in transition metal complexation.

Etik Beyan

No ethics committee approval was obtained for this research as no studies were conducted on animals or humans.

Destekleyen Kurum

Kırşehir Ahi Evran University

Proje Numarası

MMF.A4.23.007

Teşekkür

I would like to thank the Scientific Research Projects Coordination Unit of Kırşehir Ahi Evran University for supporting this study under the project number MMF.A4.23.007. Additionally, I would like to express my deep gratitude to Assoc. Prof. Tuncay Karakurt for his invaluable help and contributions to the theoretical calculations of this research.

Kaynakça

  • Ashraf, M., Wajid, A., Mahmood, K., Maah, M. J., & Yusoff, I. B. (2011). Spectral investigation of the activities of amino substituted bases. Oriental Journal of Chemistry, 27(1), 363–372.
  • Asif, M. (2019). Green synthesis of benzimidazole derivatives: an overview on green chemistry and its applications. Chemical Methodology, 3(6), 620–631. https://doi.org/10.33945/SAMI/CHEMM.2019.6.1
  • Aydınlı, E. A. (2006). Antimicrobial effects of some Schiff bases (Yüksek lisans tezi, Ankara Üniversitesi, Fen Bilimleri Enstitüsü).
  • Becke, A. D. (1993). Density‐functional thermochemistry. III. The role of exact exchange. The Journal of Chemical Physics, 98(7), 5648–5652.
  • Chang, Y. S. (2012). Hypersensitivity reactions to proton pump inhibitors. Current Opinion in Allergy and Clinical Immunology, 12(4), 348–353.
  • Dallakyan, S., & Olson, A. J. (2015). Small-molecule library screening by docking with PyRx. In J. Hempel, C. Williams, & C. Hong (Eds.), Chemical Biology Methods in Molecular Biology (Vol. 1263, pp. 243–250). Humana Press. https://doi.org/10.1007/978-1-4939-2269-7_19
  • Dennington, R., Keith, T., & Millam, J. (2009). GaussView, version 5. Semichem Inc.
  • DiRisio, R. J., Armstrong, J. E., Frank, M. A., Lake, W. R., & McNamara, W. R. (2017). Cobalt Schiff-base complexes for electrocatalytic hydrogen generation. Dalton Transactions, 46(32), 10418–10425.
  • Emregül, K. C., Düzgün, E., & Atakol, O. (2006). The application of some polydentate Schiff base compounds containing aminic nitrogens as corrosion inhibitors for mild steel in acidic media. Corrosion Science, 48(10), 3243–3260.
  • Foresman, J. B., & Frisch, A. (1996). Exploring chemistry with electronic structure methods: a guide to using Gaussian (2nd ed.). Gaussian Inc.
  • Frisch M, Trucks G, Schlegel HB, Scuseria G, Robb M, Cheeseman J, Scalmani G, Barone V, Mennucci B, Petersson G. 2009. Gaussian 09, revision A.02, Gaussian Inc, Wallingford, CT, USA, pp: 200.
  • Golcu, A., Tümer, M., Demirelli, H., & Wheatley, R. (2005). Cd(II) and Cu(II) complexes of polydentate Schiff base ligands: synthesis, characterization, properties and biological activity. Inorganica Chimica Acta, 358(6), 1785–1797.
  • Iwamoto, K., Uehara, Y., Inoue, Y., Taguchi, K., Muraoka, D., Ogo, N., Matsuno, K., & Asai, A. (2017). Inhibition of STAT3 by anticancer drug bendamustine. PLoS One, 12(1), Article e0169123.
  • Lasri, J., Elsherbiny, A. S., Eltayeb, N. E., Haukka, M., & El-Hefnawy, M. E. (2018). Synthesis and characterization of ferrocene-based Schiff base and ferrocenecarboxaldehyde oxime and their adsorptive removal of methyl blue from aqueous solution. Journal of Organometallic Chemistry, 866, 21–26.
  • Lee, C., Yang, W., & Parr, R. G. (1988). Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Physical Review B, 37(2), 785–789.
  • Lieberman, L. A., & Higgins, D. E. (2009). A small molecule screen identifies the antipsychotic drug pimozide as an inhibitor of Listeria monocytogenes infection. Antimicrobial Agents and Chemotherapy, 53(2), 756–764.
  • Pfeiffer, P., Breith, E., Lübbe, E., & Tsumaki, T. (1932). Thcylische orthokondesierte Nebenvalenzringe. Annalen der Chemie, 492(1), 81–127.
  • Politzer, P., Concha, M. C., & Murray, J. S. (2000). Density functional study of dimers of dimethylnitramine. International Journal of Quantum Chemistry, 80(2), 184–192.
  • Redshaw, C. (2017). Use of Metal Catalysts Bearing Schiff Base Macrocycles for the Ring Opening Polymerization (ROP) of Cyclic Esters. Catalysts, 7(5), 165.
  • Rehman, W., Baloch, M. K., Muhammad, B., Badshah, A., & Khan, K. M. (2004). Characteristic spectral studies and in vitro antifungal activity of some Schiff bases and their organotin (IV) complexes. Chinese Science Bulletin, 49(2), 119–122.
  • Schiff, H. (1869). Untersuchungen Uber Salicin Derivate. European Journal of Organic Chemistry, 150(3), 193–200.
  • Silva da, C. M., Silva da, D. L., Modolo, L. V., & Alves, R. B. (2011). Schiff bases: a short review of their antimicrobial activities. Journal of Advanced Research, 2(1), 1–8.
  • Upadhyay, K. K., Kumar, A., Upadhyay, S., & Mishra, P. C. (2008). Synthesis, characterization, structural optimization using density functional theory and superoxide ion scavenging activity of some Schiff bases. Journal of Molecular Structure, 873(1–3), 5–16.
  • Vigato, P. A., & Tamburini, S. (2004). The Challenge of Cyclic and Acyclic Schiff Bases and Related Derivatives. Coordination Chemistry Reviews, 248(17–20), 1717–2128.
  • Yeap, G. Y., Ha, S. T., Ishizawa, N., Suda, K., Boey, P. L., & Mahmood, W. A. K. (2003). Synthesis, crystal structure and spectroscopic study of para substituted 2-hydroxy-3- methoxybenzalideneanilines. Journal of Molecular Structure, 658(1–3), 87–99.
  • Zeishen, W., Zigi, G., & Zhenhuan, Y. (1990). Synthesis, characterization and anticanser activity of L-alanine Schiff base complexes of copper(II), zinc(II), and cobalt (II). Synthetic Reactivity in Inorganic and Metal-Organic Chemistry, 20(3), 335–344.
  • Zhang, J., Xu, L., & Wong, W. Y. (2018). Energy materials based on metal Schiff base complexes. Coordination Chemistry Reviews, 355, 180–198.
  • Zhang, P., Wang, H., Sun, L., Zhang, J., Xi, Y., Wu, Y., Yan, L. L., Li, X., & Sun, N. (2017). Telmisartan and hydrochlorothiazide antihypertensive treatmentin high sodium intake population: A randomized double blind trial. Journal of Hypertension, 35(10), 2077–2085.
Toplam 28 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Organik Kimyasal Sentez
Bölüm Araştırma Makalesi
Yazarlar

Nuriye Tuna Subaşı 0009-0005-2122-0402

Proje Numarası MMF.A4.23.007
Gönderilme Tarihi 2 Eylül 2025
Kabul Tarihi 16 Kasım 2025
Erken Görünüm Tarihi 8 Aralık 2025
Yayımlanma Tarihi 15 Ocak 2026
DOI https://doi.org/10.34248/bsengineering.1776780
IZ https://izlik.org/JA45NF56KE
Yayımlandığı Sayı Yıl 2026 Cilt: 9 Sayı: 1

Kaynak Göster

APA Subaşı, N. T. (2026). Synthesis, Spectroscopic and Theoretical Characterization of Chiral Benzimidazole-Based Schiff Bases. Black Sea Journal of Engineering and Science, 9(1), 192-205. https://doi.org/10.34248/bsengineering.1776780
AMA 1.Subaşı NT. Synthesis, Spectroscopic and Theoretical Characterization of Chiral Benzimidazole-Based Schiff Bases. BSJ Eng. Sci. 2026;9(1):192-205. doi:10.34248/bsengineering.1776780
Chicago Subaşı, Nuriye Tuna. 2026. “Synthesis, Spectroscopic and Theoretical Characterization of Chiral Benzimidazole-Based Schiff Bases”. Black Sea Journal of Engineering and Science 9 (1): 192-205. https://doi.org/10.34248/bsengineering.1776780.
EndNote Subaşı NT (01 Ocak 2026) Synthesis, Spectroscopic and Theoretical Characterization of Chiral Benzimidazole-Based Schiff Bases. Black Sea Journal of Engineering and Science 9 1 192–205.
IEEE [1]N. T. Subaşı, “Synthesis, Spectroscopic and Theoretical Characterization of Chiral Benzimidazole-Based Schiff Bases”, BSJ Eng. Sci., c. 9, sy 1, ss. 192–205, Oca. 2026, doi: 10.34248/bsengineering.1776780.
ISNAD Subaşı, Nuriye Tuna. “Synthesis, Spectroscopic and Theoretical Characterization of Chiral Benzimidazole-Based Schiff Bases”. Black Sea Journal of Engineering and Science 9/1 (01 Ocak 2026): 192-205. https://doi.org/10.34248/bsengineering.1776780.
JAMA 1.Subaşı NT. Synthesis, Spectroscopic and Theoretical Characterization of Chiral Benzimidazole-Based Schiff Bases. BSJ Eng. Sci. 2026;9:192–205.
MLA Subaşı, Nuriye Tuna. “Synthesis, Spectroscopic and Theoretical Characterization of Chiral Benzimidazole-Based Schiff Bases”. Black Sea Journal of Engineering and Science, c. 9, sy 1, Ocak 2026, ss. 192-05, doi:10.34248/bsengineering.1776780.
Vancouver 1.Subaşı NT. Synthesis, Spectroscopic and Theoretical Characterization of Chiral Benzimidazole-Based Schiff Bases. BSJ Eng. Sci. [Internet]. 01 Ocak 2026;9(1):192-205. Erişim adresi: https://izlik.org/JA45NF56KE

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