SavedAdd your journal

Journals / Turkish Journal of Chemistry / 2018 / Cilt: 42 - Sayı: 5

Synthesis and biological evaluation of quinoline-triazole and quinolone-triazole conjugates

Ayşegül GÜMÜŞ
Veysi OKUMUŞ
Pages
1344–1357
Publication Date
2018-10-11
DOI
—
🏛️Bibliographic metadata and full text access for this article are provided via DergiPark.
DergiPark Record ↗
✨

AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

Furthermore, the antibacterial activity was studied against gram-positive and gram-negative bacteria and the DNA binding ability of the compounds was evaluated with calf thymus DNA using agarose gel electrophoresis.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:One-pot synthesis of novel quinoline- and quinolone-substituted 1,2,3-triazoles has been performed from the key intermediates, quinoline- and quinolone-substituted propargyl derivatives 1-3 (48%-88% yields).
📊
Key Findings & Data:The antioxidant properties of the newly synthesized compounds, 1a-1c, 2a-2c, and 3a-3c, were evaluated by monitoring DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging abilities, metal chelating effects, and reducing power.
💡
Conclusion & Impact:Furthermore, the antibacterial activity was studied against gram-positive and gram-negative bacteria and the DNA binding ability of the compounds was evaluated with calf thymus DNA using agarose gel electrophoresis.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Quinoline · quinolone · triazole

Abstract

One-pot synthesis of novel quinoline- and quinolone-substituted 1,2,3-triazoles has been performed from the key intermediates, quinoline- and quinolone-substituted propargyl derivatives 1-3 (48%-88% yields). The antioxidant properties of the newly synthesized compounds, 1a-1c, 2a-2c, and 3a-3c, were evaluated by monitoring DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging abilities, metal chelating effects, and reducing power. The scavenging effects of compounds on the free radical decreased in the order of 3b>>> 3a>>> 1b} and were found to be 36.3%, 34.9%, and 27.6% at the concentration of 500 μμ\mu g/mL, respectively. All of the compounds showed low chelating capacity. Furthermore, the antibacterial activity was studied against gram-positive and gram-negative bacteria and the DNA binding ability of the compounds was evaluated with calf thymus DNA using agarose gel electrophoresis.

🔖

Cite This Article

GÜMÜŞ, A., OKUMUŞ, V. (2018). Synthesis and biological evaluation of quinoline-triazole and quinolone-triazole conjugates. Turkish Journal of Chemistry, Cilt: 42 - Sayı: 5, 1344–1357. https://ajindex.com/articles/184278

📄 Full Text PDF Viewer

📄

PDF görüntüleyici hazırlanıyor...

References (23)

  1. Esvaran, S.; Adhikari, A. V.; Shetty, N. S. Eur. J. Med. Chem. 2009, 44, 4637-4647.
  2. Clemons, M.; Coleman, R. E.; Verma, S. Cancer Treat Rev. 2004, 30, 325-332.
  3. Radhika, C.; Venkatesham, A.; Sarangapani, M. Med. Chem. Res. 2012, 21, 3509-3513.
  4. Kumar, S. S.; Kavitha, H. P. Mini-Rev. Org. Chem. 2013, 10, 40-65.
  5. Plech, T.; Luszczki, J. J.; Wujec, M.; Flieger, J.; Pizon, M. Eur. J. Med. Chem. 2013, 60, 208-215.
  6. Patel, N. B.; Khan, I. H.; Pannecouque, C., Clercq, E. D. Med. Chem. Res. 2013, 22, 1320-1329.
  7. Chaudhary, P. M.; Chavan, S. R.; Shirazi, F.; Razdan, M.; Nimkar, P.; Maybhate, S. P.; Likhite, A. P.; Gonnade, R.; Hazara, B. G.; Deshpande, S. R. Bioorg. Med. Chem. Lett. 2009, 17, 2433-2440.
  8. Huisgen, R. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A.; Ed. Wiley: New York, NY, USA, 1984.
  9. Appukkuttan, P.; Dehaen, W.; Fokin, V. V.; der Eycken, E. V. Org. Lett. 2004, 6, 4223-4225.
  10. Gümüş, A.; Uçur, S. Heterocycl. Commun. 2014, 20, 361-364.
  11. Kumar, S.; Bawa, S.; Gupta, H. Mini-Rev. Med. Chem. 2009, 9, 1648-1654.
  12. Chen, Y. L.; Huang, C. J.; Huang, Z. Y.; Tseng, C. H.; Chang, F. S.; Yang, S. H.; Lin, S. R.; Tzeng, C. C. Bioorg. Med. Chem. 2006, 14, 3098-3105.
  13. Chen, Y. L.; Zhao, Y. L.; Lu, C. M.; Tzeng, C. C.; Wang, J. P. Bioorg. Med. Chem. 2006, 14, 4373-4378.
  14. Feng, Y.; Lau, E.; Scortegagna, M.; Ruller, C.; De, S. K.; Barile, E.; Krajewski, S.; Aza-Blanc, P.; Williams, R.; Pinkerton, A. B. et al. Pigm. Cell Melanoma Res. 2013, 26, 136-142.
  15. Gholap, A. R.; Toti, K. S.; Shirazi, F.; Kumari, R.; Bhat, M. K.; Deshpande, M. V.; Srinivasan, K. V. Bioorg. Med. Chem. 2007, 15, 6705-6715.
  16. Krafts, K.; Hempelmann, E.; Skorska-Stania, A. Parasitol. Res. 2012, 111, 1-6.
  17. Sanchez, J. P.; Domagala, J. M.; Hagen, S. E.; Heifetz, C. L.; Hutt, M. P.; Nichols, J. B.; Trehan, A. K. J. Med. Chem. 1988, 31, 983-991.
  18. Sabatini, S.; Gosetto, F.; Manfroni, G.; Tabarrini, O.; Kaatz, G. W.; Patel, D.; Cecchetti, V. J. Med. Chem. 2011, 54, 5722-5736.
  19. Srinivasan, S.; Shafreen, R. M. B.; Nithyanand, P.; Manisankar, P.; Pandian, S. K. Eur. J. Med. Chem. 2010, 45, 6101-6105.
  20. Wang, Y.; Damu, G. L. V.; Lv, J. S.; Geng, R. X.; Yang, D. C.; Zhou, C. H. Bioorg. Med. Chem. Lett. 2012, 22, 5363-5366.
  21. Truong, V. V.; Nam, T. D.; Hung, T. N.; Nga, N. T.; Quan, P. M.; Chinh, L. V.; Jung, S. H. Bioorg. Med. Chem. Lett. 2015, 25, 5182-5185.
  22. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem. Int. Ed. 2002, 41, 2596-2599.
  23. Feldman, A. K.;