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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

Yıl 2023, Cilt: 7 Sayı: 2, 171 - 179, 31.12.2023

Selbi Keskin Derya Vural

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

Öz

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.

Anahtar Kelimeler

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

Kaynakça

  • 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.

Yıl 2023, Cilt: 7 Sayı: 2, 171 - 179, 31.12.2023

Selbi Keskin Derya Vural

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

Öz

Kaynakça

  • 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.
Toplam 48 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Biyokimya ve Hücre Biyolojisi (Diğer), Klasik Fizik (Diğer)
Bölüm Makale
Yazarlar

Selbi Keskin 0000-0003-0664-9903

Derya Vural 0000-0002-0120-3024

Erken Görünüm Tarihi 9 Ocak 2024
Yayımlanma Tarihi 31 Aralık 2023
Gönderilme Tarihi 4 Kasım 2023
Kabul Tarihi 20 Aralık 2023
Yayımlandığı Sayı Yıl 2023 Cilt: 7 Sayı: 2

Kaynak Göster

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. Aralık 2023;7(2):171-179. doi:10.32571/ijct.1386211
Chicago Keskin, Selbi, ve 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, sy. 2 (Aralık 2023): 171-79. https://doi.org/10.32571/ijct.1386211.
EndNote Keskin S, Vural D (01 Aralık 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 ve 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., c. 7, sy. 2, ss. 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 (Aralık 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 ve 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, c. 7, sy. 2, 2023, ss. 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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