Synthesis of acetamide derivatives of 1,2,4-triazole bearing azinane and their binding interactions with bovine serum albumin using spectroscopic techniques

Synthesis of acetamide derivatives of 1,2,4-triazole bearing azinane and their binding interactions with bovine serum albumin using spectroscopic techniques

A new series of acetamide derivatives containing 1,2,4-triazole and azinane moieties has been synthesizedand characterized using 1 H NMR, 13 C NMR, IR, and EI-MS spectroscopic analysis. The intermediate triazole wassynthesized through a sequential synthesis of carboxylate and carbohydrazide. The bovine serum albumin (BSA) bindingof the newly synthesized 1,2,4-triazole derivatives was evaluated along with thermodynamics, site-selective binding, andsynchronous study. The results obtained by BSA binding as well as thermodynamic studies justify that all the compoundsshow spontaneous interaction with BSA and could be effectively distributed and eliminated from the body. Therefore,the triazole-based analogs might be a useful strategy for designing new drug systems.

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  • 1. Rehman, A. U.; Iqbal, J.; Abbasi, M. A,; Siddiqui, S. Z.; Khalid, H.; Laulloo, S. J.; Virk, N. A.; Rasool, S.; Shah, S. A. A. Cogent Chem. 2018, 4, 1-16.
  • 2. Jiaxin, F. U.; Kaiwei, W.; Yushu, G. E.; Fenglei, J.; Xiaohong, S.; Yang, L.; Yi, L. Sci. China Chem. 2011, 54, 788-796.
  • 3. Qingpeng, W.; Jingqing, Z.; Guri, D.; Kun, W.; Huizhen, Z.; Chenghe, Z. Sci. China Chem. 2012, 55, 2134-2153.
  • 4. Mitsumori, T.; Bendikov, M.; Sedó, J.; Wudl, F. Chem. Mater. 2003, 15, 3759-3768.
  • 5. Zbancioc, G. N.; Mangalagiu, I. I. Tetrahedron 2010, 66, 278-282.
  • 6. Tozkoparan, B.; Kupeli, E.; Yesilada, E.; Ertan, M. Bioorg. Med. Chem. 2007, 15, 1808-1814.
  • 7. Rabea, S. M.; El-Koussi, N. A.; Hassan, H. Y.; Aboul-Fadl, V. Arch. Pharm. 2006, 339, 32-40.
  • 8. Abdel-Aal, M. T.; El-Sayed, W. A.; El-Kosy, S. M.; El-Ashry, S. H. Arch. Pharm. 2008, 341, 307-313.
  • 9. Dumitrascu, F.; Caproiu, M. T.; Georgescu, F.; Draghici, B.; Popa, M. M.; Georgescu, E. Synlett 2010, 2407-2410.
  • 10. Jones, D. H.; Slack, R.; Squires, S.; Wooldridge, K. R. H. J. Med. Chem. 1965, 8, 676-680.
  • 11. Ilango, K.; Valentina, P. Pharm. Chem. 2010, 2, 16-22.
  • 12. Sughen, J. K.; Yoloye, T. Pharm. Acta Helv. 1978, 58, 64-68.
  • 13. Shams, E. S. A.; Hazzaa, A. A. B. Pharmazie 1974, 29, 761-763.
  • 14. Oruc, E. E.; Rollas, S.; Kandemirli, F.; Shvets, N.; Dimoglo, A. S. Bioorg. Med. Chem. Lett. 2004, 12, 5651-5659.
  • 15. Wu, G.; Ouyang, L.; Liu, J.; Zeng, S.; Huang, W.; Han, B.; Wu, F.; He, G.; Xiang, M. Mol. Diversity 2013, 17, 271-283.
  • 16. Duan, Y. Q.; Lei, H. G.; Min, S. G.; Duan, Z. Q. Spectrosc. Spect. Anal. 2009, 29, 2998-3002.
  • 17. Jiang, H.; Chen, R.; Pu, H. J. Lumin. 2012, 132, 592-599.
  • 18. Ghosh, S.; Dey, J. J. Colloid Interface Sci. 2015, 458, 284-292.
  • 19. Zhang, H. M.; Fei, Z. H.; Tang, B. P.; Chen, J.; Tao, W. H.; Wang, Y. Q. Mol. Biol. Rep. 2012, 39, 4937-4947.
  • 20. Valstar, A.; Almgren, M.; Brown, W.; Vasilescu, M. Langmuir 2000, 16, 922-927. 21. Prashant, M. K.; Madaiah, M.; Revanasiddappa, H. D. Organic Chemistry 2013, 2013, 1-12.
  • 22. Teng, Y.; Liu, R.; Yan, S.; Pan, X.; Zhang, P.; Wang, M. J. Fluoresc. 2010, 20, 381-387.
  • 23. Ghosh, S.; Jana, S.; Guchhait, N. J. Phys. Chem. 2012, 116, 1155-1163.
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK