Research Article
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Synthesis, characterization and molecular docking studies of novel Schiff bases bearing 1-(o-tolyl)-4-(phenoxymethyl)-(1H)1,2,3-triazole derivatives

Year 2023, Volume: 7 Issue: 2, 171 - 179, 31.12.2023

Selbi Keskin , Derya Vural

https://doi.org/10.32571/ijct.1386211

Abstract

Compounds including a triazole skeleton and an imine functional group in their structures have a broad range of applications in drug discovery due to their biological activities. Herein, the novel Schiff bases bearing 1-(o-tolyl)-4-(phenoxymethyl)-(1H)1,2,3-triazole derivatives were synthesized and the structures of newly synthesized compounds were characterized by FTIR, 1D and 2D NMR and mass spectral data. Computational analysis was performed to optimize the structures of the synthesized compounds with density functional theory (DFT) using the B3LYP method at the 6-311++G(d,p) basis set in the gas phase. The binding affinity values obtained from docking studies of Schiff bases (2a-2d) on sterol 14α-demethylase (CYP51) indicate that compounds 2c and 2d have a higher potential as CYP51 inhibitors compared to compounds 2a and 2b. It was found that the incorporation of a benzene ring into the structure significantly increased the binding affinity from -9.0 to -11.5 kcal mol-1.

Keywords

Schiff bases 1,2,3-triazole molecular docking sterol 14α-demethylase

References

  • Bock, V. D.; Hiemstra, H.; Van Maarseveen, J. H. European J. Org. Chem. 2006, 51-68.
  • Meldal, M.; Tornoe, C. W. Chem. Rev. 2008, 108, 2952-3015.
  • Hein, J. E.; Fokin, V. V. Chem. Soc. Rev. 2010, 39 (4), 1302-1315.
  • Lima-Neto, R. G.; Cavalcante, N. N. M.; Srivastava, R. M.; Mendonça, F. J. B.; Wanderley, A. G.; Neves, R. P.; Dos Anjos, J. V. Molecules 2012, 17, 5882-5892.
  • Dai, Z.-C.; Chen, Y.-F.; Zhang, M.; Li, S.-K.; Yang, T.-T.; Shen, L.; Wang, J.-X.; Qian, S.-S.; Zhu, H.-L.; Ye, Y.-H. Org. Biomol. Chem 2015, 13, 477-486.
  • Aher, N. G.; Pore, V. S.; Mishra, N. N.; Kumar, A.; Shukla, P. K.; Sharma, A.; Bhat, M. K. Bioorganic Med. Chem. Lett. 2009, 19, 759-763.
  • Shaikh, M. H.; Subhedar, D. D.; Khedkar, V. M.; Jha, P. C.; Khan, F. A. K.; Sangshetti, J. N.; Shingate, B. B. Chinese Chem. Lett. 2016, 27, 1058-1063.
  • Teixeira, R. R.; Gazolla, P. A. R.; da Silva, A. M.; Borsodi, M. P. G.; Bergmann, B. R.; Ferreira, R. S.; Vaz, B. G.; Vasconcelos, G. A.; Lima, W. P. Eur. J. Med. Chem. 2018, 146, 274-286.
  • Surineni, G.; Yogeeswari, P.; Sriram, D.; Kantevari, S. Med. Chem. Res. 2015, 24, 1298-1309.
  • Boechat, N.; Ferreira, V. F.; Ferreira, S. B.; Ferreira, M. D. L. G.; Da Silva, F. D. C.; Bastos, M. M.; Costa, M. D. S.; Lourenço, M. C. S.; Pinto, A. C.; Krettli, A. U.; Aguiar, A. C.; Teixeira, B. M.; Da Silva, N. V.; Martins, P. R. C.; Bezerra, F. A. F. M.; Camilo, A. L. S.; Da Silva, G. P.; Costa, C. C. P. J. Med. Chem. 2011, 54, 5988-5999.
  • Viegas, D. J.; da Silva, V. D.; Buarque, C. D.; Bloom, D. C.; Abreu, P. A. Antivir. Ther. 2020, 25, 399-410.
  • Jordão, A. K.; Afonso, P. P.; Ferreira, V. F.; de Souza, M. C. B. V.; Almeida, M. C. B.; Beltrame, C. O.; Paiva, D. P.; Wardell, S. M. S. V.; Wardell, J. L.; Tiekink, E. R. T.; Damaso, C. R.; Cunha, A. C. Eur. J. Med. Chem. 2009, 44, 3777-3783.
  • Monceaux, C. J.; Hirata-Fukae, C.; Lam, P. C. H.; Totrov, M. M.; Matsuoka, Y.; Carlier, P. R. Bioorganic Med. Chem. Lett. 2011, 21, 3992-3996.
  • Dong, H. R.; Wu, J. G. Heterocycl. Commun. 2018, 24, 109-112.
  • Gaddameedi, J. D.; Yedla, P.; Kuchukulla, R. R.; Chavva, K.; Pillalamarri, S. R.; Gautham, S. K.; Chityal, G. K.; Banda, N. J. Heterocycl. Chem. 2017, 54, 194-205.
  • Vincent-Ballereau, F. N.; Patey, O. N.; Lafaix, C. Pharm. Weekbl. Sci. Ed. 1991, 13, 45-57.
  • Pasko, M. T.; Piscitelli, S. C.; Van Slooten, A. D. Ann. Pharmacother. 1990, 24, 860-867.
  • Dong, J.; Zhu, D.; Chen, M.; Wang, T.; Gao, Y.; Liu, W. Thorac. Cancer 2022, 13, 1513-1524.
  • Wheless, J. W.; Vazques, B. V. Curr. Rev. Clin. Sci. 2010, 10, 1-6.
  • Kabak, M.; Elmali, A.; Elerman, Y. J. Mol. Struct. 1999, 477, 151-158.
  • Patai, S. The Chemistry of the Carbon-Nitrogen Double Bond. In Interscience; New York, 1970; pp 149-180.
  • Raju, S. K.; Settu, A.; Thiyagarajan, A.; Rama, D.; Sekar, P.; Kumar, S. GSC Biol. Pharm. Sci. 2022, 21, 203-215.
  • Dzeikala, A.; Sykula, A. J. Pharm. Pharmacol. 2018, 6, 989-1009.
  • Arulmurugan, S.; Kavitha, H. P.; Venkatraman, B. R. Rasayan J. Chem. 2010, 3, 385-410.
  • Da Silva, C. M.; Da Silva, D. L.; Modolo, L. V.; Alves, R. B.; De Resende, M. A.; Martins, C. V. B.; De Fátima, Â. J. Adv. Res. 2011, 2, 1-8.
  • Almutairi, M. S.; Zakaria, A. S.; Ignasius, P. P.; Al-Wabli, R. I.; Joe, I. H.; Attia, M. I. J. Mol. Struct. 2018, 1153, 333-345.
  • Ali, M. T.; Blicharska, N.; Shilpi, J. A.; Seidel, V. Sci. Rep. 2018, 8:12238, 1-8.
  • Lepesheva, G. I.; Waterman, M. R. Biochim. Biophys. Acta 2007, 1770, 467-477.
  • Lepesheva, G. I.; Waterman, M. R. Curr. Top. Med. Chem. 2011, 11, 2060-2071.
  • Hargrove, T. Y.; Wawrzak, Z.; Liu, J.; Waterman, M. R.; Nes, W. D.; Lepesheva, G. I. J. Lipid Res. 2012, 53, 311-320.
  • Fan, J.; Urban, M.; Parker, J. E.; Brewer, H. C.; Kelly, S. L.; Hammond-Kosack, K. E.; Fraaije, B. A.; Liu, X.; Cools, H. J. New Phytol. 2013, 198, 821-835.
  • Friggeri, L.; Hargrove, T. Y.; Wawrzak, Z.; Guengerich, F. P.; Lepesheva, G. I. J. Med. Chem. 2019, 62, 10391-10401.
  • Kumar, A.; Lal, K.; Poonia, N.; Kumar, A.; Kumar, A. Res. Chem. Intermed. 2022, 48, 2933-2948.
  • Fu, X. W.; Pu, W. C.; Zhang, G. L.; Wang, C. Res. Chem. Intermed. 2015, 41, 8147-8158.
  • Awolade, P.; Cele, N.; Kerru, N.; Singh, P. Mol. Divers. 2021, 25, 2201-2218.
  • Xie, S.; Zhang, Y.; Ramström, O.; Yan, M. Chem. Sci. 2016, 7, 713-718.
  • Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; G. E. Scuseria, et al. Gaussian 09, Revision C.01. Gaussian Inc. Wallingford, CT 2009.
  • Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
  • Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
  • Dennington, R.; Keith, T.; Millam, J. GaussView, Version 5. Semichem Inc. Shawnee Mission 2009.
  • Trott, O.; Olson, A. J. J. Comput. Chem. 2010, 31, 455-461.
  • Berman, H. M.; Westbrook, J.; Feng, Z.; Gilliland, G.; Bhat, T. N.; Weissig, H.; Shindyalov, I. N.; Bourne, P. E. Nucleic Acids Res. 2000, 28, 235-242.
  • Morris, G. M.; Huey, R.; Lindstrom, W.; Sanner, M. F.; Belew, R. K.; Goodsell, D. S.; Olson, A. J. J. Comput. Chem. 2009, 30, 2785-2791.
  • BIOVIA, Dassault Systemes, Discovery Studio Modeling Environment, Release 2017, San Diego; 2016. Keskin, S.; Balci, M. Org. Lett. 2015, 17, 964-967.
  • Keskin, S. ChemistrySelect 2023, 8, e202302133 (1-7).
  • Bisht, R.; Chattopadhyay, B. J. Am. Chem. Soc. 2016, 138 (1), 84-87.
  • Yeap, G. Y.; Heng, B. T. J. Chem. Sci. 2014, 126 (1), 247-254.
  • Peng, W.; Zhu, S. J. Fluor. Chem. 2002, 116, 81-86.

Year 2023, Volume: 7 Issue: 2, 171 - 179, 31.12.2023

Selbi Keskin , Derya Vural

https://doi.org/10.32571/ijct.1386211

Abstract

References

  • Bock, V. D.; Hiemstra, H.; Van Maarseveen, J. H. European J. Org. Chem. 2006, 51-68.
  • Meldal, M.; Tornoe, C. W. Chem. Rev. 2008, 108, 2952-3015.
  • Hein, J. E.; Fokin, V. V. Chem. Soc. Rev. 2010, 39 (4), 1302-1315.
  • Lima-Neto, R. G.; Cavalcante, N. N. M.; Srivastava, R. M.; Mendonça, F. J. B.; Wanderley, A. G.; Neves, R. P.; Dos Anjos, J. V. Molecules 2012, 17, 5882-5892.
  • Dai, Z.-C.; Chen, Y.-F.; Zhang, M.; Li, S.-K.; Yang, T.-T.; Shen, L.; Wang, J.-X.; Qian, S.-S.; Zhu, H.-L.; Ye, Y.-H. Org. Biomol. Chem 2015, 13, 477-486.
  • Aher, N. G.; Pore, V. S.; Mishra, N. N.; Kumar, A.; Shukla, P. K.; Sharma, A.; Bhat, M. K. Bioorganic Med. Chem. Lett. 2009, 19, 759-763.
  • Shaikh, M. H.; Subhedar, D. D.; Khedkar, V. M.; Jha, P. C.; Khan, F. A. K.; Sangshetti, J. N.; Shingate, B. B. Chinese Chem. Lett. 2016, 27, 1058-1063.
  • Teixeira, R. R.; Gazolla, P. A. R.; da Silva, A. M.; Borsodi, M. P. G.; Bergmann, B. R.; Ferreira, R. S.; Vaz, B. G.; Vasconcelos, G. A.; Lima, W. P. Eur. J. Med. Chem. 2018, 146, 274-286.
  • Surineni, G.; Yogeeswari, P.; Sriram, D.; Kantevari, S. Med. Chem. Res. 2015, 24, 1298-1309.
  • Boechat, N.; Ferreira, V. F.; Ferreira, S. B.; Ferreira, M. D. L. G.; Da Silva, F. D. C.; Bastos, M. M.; Costa, M. D. S.; Lourenço, M. C. S.; Pinto, A. C.; Krettli, A. U.; Aguiar, A. C.; Teixeira, B. M.; Da Silva, N. V.; Martins, P. R. C.; Bezerra, F. A. F. M.; Camilo, A. L. S.; Da Silva, G. P.; Costa, C. C. P. J. Med. Chem. 2011, 54, 5988-5999.
  • Viegas, D. J.; da Silva, V. D.; Buarque, C. D.; Bloom, D. C.; Abreu, P. A. Antivir. Ther. 2020, 25, 399-410.
  • Jordão, A. K.; Afonso, P. P.; Ferreira, V. F.; de Souza, M. C. B. V.; Almeida, M. C. B.; Beltrame, C. O.; Paiva, D. P.; Wardell, S. M. S. V.; Wardell, J. L.; Tiekink, E. R. T.; Damaso, C. R.; Cunha, A. C. Eur. J. Med. Chem. 2009, 44, 3777-3783.
  • Monceaux, C. J.; Hirata-Fukae, C.; Lam, P. C. H.; Totrov, M. M.; Matsuoka, Y.; Carlier, P. R. Bioorganic Med. Chem. Lett. 2011, 21, 3992-3996.
  • Dong, H. R.; Wu, J. G. Heterocycl. Commun. 2018, 24, 109-112.
  • Gaddameedi, J. D.; Yedla, P.; Kuchukulla, R. R.; Chavva, K.; Pillalamarri, S. R.; Gautham, S. K.; Chityal, G. K.; Banda, N. J. Heterocycl. Chem. 2017, 54, 194-205.
  • Vincent-Ballereau, F. N.; Patey, O. N.; Lafaix, C. Pharm. Weekbl. Sci. Ed. 1991, 13, 45-57.
  • Pasko, M. T.; Piscitelli, S. C.; Van Slooten, A. D. Ann. Pharmacother. 1990, 24, 860-867.
  • Dong, J.; Zhu, D.; Chen, M.; Wang, T.; Gao, Y.; Liu, W. Thorac. Cancer 2022, 13, 1513-1524.
  • Wheless, J. W.; Vazques, B. V. Curr. Rev. Clin. Sci. 2010, 10, 1-6.
  • Kabak, M.; Elmali, A.; Elerman, Y. J. Mol. Struct. 1999, 477, 151-158.
  • Patai, S. The Chemistry of the Carbon-Nitrogen Double Bond. In Interscience; New York, 1970; pp 149-180.
  • Raju, S. K.; Settu, A.; Thiyagarajan, A.; Rama, D.; Sekar, P.; Kumar, S. GSC Biol. Pharm. Sci. 2022, 21, 203-215.
  • Dzeikala, A.; Sykula, A. J. Pharm. Pharmacol. 2018, 6, 989-1009.
  • Arulmurugan, S.; Kavitha, H. P.; Venkatraman, B. R. Rasayan J. Chem. 2010, 3, 385-410.
  • Da Silva, C. M.; Da Silva, D. L.; Modolo, L. V.; Alves, R. B.; De Resende, M. A.; Martins, C. V. B.; De Fátima, Â. J. Adv. Res. 2011, 2, 1-8.
  • Almutairi, M. S.; Zakaria, A. S.; Ignasius, P. P.; Al-Wabli, R. I.; Joe, I. H.; Attia, M. I. J. Mol. Struct. 2018, 1153, 333-345.
  • Ali, M. T.; Blicharska, N.; Shilpi, J. A.; Seidel, V. Sci. Rep. 2018, 8:12238, 1-8.
  • Lepesheva, G. I.; Waterman, M. R. Biochim. Biophys. Acta 2007, 1770, 467-477.
  • Lepesheva, G. I.; Waterman, M. R. Curr. Top. Med. Chem. 2011, 11, 2060-2071.
  • Hargrove, T. Y.; Wawrzak, Z.; Liu, J.; Waterman, M. R.; Nes, W. D.; Lepesheva, G. I. J. Lipid Res. 2012, 53, 311-320.
  • Fan, J.; Urban, M.; Parker, J. E.; Brewer, H. C.; Kelly, S. L.; Hammond-Kosack, K. E.; Fraaije, B. A.; Liu, X.; Cools, H. J. New Phytol. 2013, 198, 821-835.
  • Friggeri, L.; Hargrove, T. Y.; Wawrzak, Z.; Guengerich, F. P.; Lepesheva, G. I. J. Med. Chem. 2019, 62, 10391-10401.
  • Kumar, A.; Lal, K.; Poonia, N.; Kumar, A.; Kumar, A. Res. Chem. Intermed. 2022, 48, 2933-2948.
  • Fu, X. W.; Pu, W. C.; Zhang, G. L.; Wang, C. Res. Chem. Intermed. 2015, 41, 8147-8158.
  • Awolade, P.; Cele, N.; Kerru, N.; Singh, P. Mol. Divers. 2021, 25, 2201-2218.
  • Xie, S.; Zhang, Y.; Ramström, O.; Yan, M. Chem. Sci. 2016, 7, 713-718.
  • Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; G. E. Scuseria, et al. Gaussian 09, Revision C.01. Gaussian Inc. Wallingford, CT 2009.
  • Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
  • Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
  • Dennington, R.; Keith, T.; Millam, J. GaussView, Version 5. Semichem Inc. Shawnee Mission 2009.
  • Trott, O.; Olson, A. J. J. Comput. Chem. 2010, 31, 455-461.
  • Berman, H. M.; Westbrook, J.; Feng, Z.; Gilliland, G.; Bhat, T. N.; Weissig, H.; Shindyalov, I. N.; Bourne, P. E. Nucleic Acids Res. 2000, 28, 235-242.
  • Morris, G. M.; Huey, R.; Lindstrom, W.; Sanner, M. F.; Belew, R. K.; Goodsell, D. S.; Olson, A. J. J. Comput. Chem. 2009, 30, 2785-2791.
  • BIOVIA, Dassault Systemes, Discovery Studio Modeling Environment, Release 2017, San Diego; 2016. Keskin, S.; Balci, M. Org. Lett. 2015, 17, 964-967.
  • Keskin, S. ChemistrySelect 2023, 8, e202302133 (1-7).
  • Bisht, R.; Chattopadhyay, B. J. Am. Chem. Soc. 2016, 138 (1), 84-87.
  • Yeap, G. Y.; Heng, B. T. J. Chem. Sci. 2014, 126 (1), 247-254.
  • Peng, W.; Zhu, S. J. Fluor. Chem. 2002, 116, 81-86.
There are 48 citations in total.

Details

Primary Language English
Subjects Biochemistry and Cell Biology (Other), Classical Physics (Other)
Journal Section Research Articles
Authors

Selbi Keskin 0000-0003-0664-9903

Derya Vural 0000-0002-0120-3024

Early Pub Date January 9, 2024
Publication Date December 31, 2023
Submission Date November 4, 2023
Acceptance Date December 20, 2023
Published in Issue Year 2023 Volume: 7 Issue: 2

Cite

APA Keskin, S., & Vural, D. (2023). Synthesis, characterization and molecular docking studies of novel Schiff bases bearing 1-(o-tolyl)-4-(phenoxymethyl)-(1H)1,2,3-triazole derivatives. International Journal of Chemistry and Technology, 7(2), 171-179. https://doi.org/10.32571/ijct.1386211
AMA Keskin S, Vural D. Synthesis, characterization and molecular docking studies of novel Schiff bases bearing 1-(o-tolyl)-4-(phenoxymethyl)-(1H)1,2,3-triazole derivatives. Int. J. Chem. Technol. December 2023;7(2):171-179. doi:10.32571/ijct.1386211
Chicago Keskin, Selbi, and Derya Vural. “Synthesis, Characterization and Molecular Docking Studies of Novel Schiff Bases Bearing 1-(o-Tolyl)-4-(phenoxymethyl)-(1H)1,2,3-Triazole Derivatives”. International Journal of Chemistry and Technology 7, no. 2 (December 2023): 171-79. https://doi.org/10.32571/ijct.1386211.
EndNote Keskin S, Vural D (December 1, 2023) Synthesis, characterization and molecular docking studies of novel Schiff bases bearing 1-(o-tolyl)-4-(phenoxymethyl)-(1H)1,2,3-triazole derivatives. International Journal of Chemistry and Technology 7 2 171–179.
IEEE S. Keskin and D. Vural, “Synthesis, characterization and molecular docking studies of novel Schiff bases bearing 1-(o-tolyl)-4-(phenoxymethyl)-(1H)1,2,3-triazole derivatives”, Int. J. Chem. Technol., vol. 7, no. 2, pp. 171–179, 2023, doi: 10.32571/ijct.1386211.
ISNAD Keskin, Selbi - Vural, Derya. “Synthesis, Characterization and Molecular Docking Studies of Novel Schiff Bases Bearing 1-(o-Tolyl)-4-(phenoxymethyl)-(1H)1,2,3-Triazole Derivatives”. International Journal of Chemistry and Technology 7/2 (December 2023), 171-179. https://doi.org/10.32571/ijct.1386211.
JAMA Keskin S, Vural D. Synthesis, characterization and molecular docking studies of novel Schiff bases bearing 1-(o-tolyl)-4-(phenoxymethyl)-(1H)1,2,3-triazole derivatives. Int. J. Chem. Technol. 2023;7:171–179.
MLA Keskin, Selbi and Derya Vural. “Synthesis, Characterization and Molecular Docking Studies of Novel Schiff Bases Bearing 1-(o-Tolyl)-4-(phenoxymethyl)-(1H)1,2,3-Triazole Derivatives”. International Journal of Chemistry and Technology, vol. 7, no. 2, 2023, pp. 171-9, doi:10.32571/ijct.1386211.
Vancouver Keskin S, Vural D. Synthesis, characterization and molecular docking studies of novel Schiff bases bearing 1-(o-tolyl)-4-(phenoxymethyl)-(1H)1,2,3-triazole derivatives. Int. J. Chem. Technol. 2023;7(2):171-9.

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