Selçuk GÜMÜŞ, Ayşegül GÜMÜŞ, Veysi OKUMUŞ

Synthesis of 2-substituted 8-propargyloxyquinoline derivatives and determination of their antioxidant, antibacterial, and DNA binding activities

2-Substituted 8-propargyloxyquinoline derivatives have been synthesized from 2-substituted-8-hydroxyquinolinesby O-propargylation method (30%–98% yields). The newly synthesized compounds were tested for in vitro antioxidantactivities such as DPPH radical scavenging, ferrous chelating, and reducing power activities. The maximum radical scavenging (46.5%) and reducing power activities were obtained from 1 and maximum ferrous chelating effect was obtainedfrom 6 (72.1%) at the concentration of 500 µg/mL. To indicate DNA binding activity of the complexes calf thymusDNA was used. The compounds were also evaluated for their antimicrobial activity against three gram-positive and threegram-negative bacteria. Compounds 3 and 5 exhibited antibacterial activity against all tested gram-positive bacteria.

PDF

___

1. Katritzky, A. R.; Ramsden, C.; Scriven, E.; Taylor, R. J. K. Comprehensive Heterocyclic Chemistry, Vols. 1–15; Elsevier: Amsterdam, the Netherlands, 2010.
2. Majumdar, K. C.; Chattopadhyay, S. K. Heterocycles in Natural Product Synthesis; Wiley: New York, NY, USA, 2011.
3. Dua, R.; Shrivastava, S.; Sonwane, S. K.; Srivastava, S. K. Advances in Biological Research 2011, 5, 120-144.
4. Lilienkampf, A.; Mao, J.; Wan, B.; Wang, Y.; Franzblau, S. G.; Kozikowski, A. P. J. Med. Chem. 2009, 52, 2109-2118.
5. Nasveld, P.; Kitchener, S. Trans. R. Soc. Trop. Med. Hyg. 2005, 99, 2-5.
6. Leatham, P. A.; Bird, H. A.; Wright, V.; Seymour, D.; Gordon, A. Eur. J. Rheumatol. Infl. 1983, 6, 209-211.
7. Denny, W. A.; Wilson, W. R.; Ware, D. C.; Atwell, G. J.; Milbank, J. B.; Stevenson, R. J. U.S. Patent 2006, 7064117.
8. Mahamoud, A.; Chevalier, J.; Davin-Regli, A.; Barbe, J.; Pages, J. M. Curr. Drug. Target 2006, 7, 843-847.
9. Muruganantham, N.; Sivakumar, R.; Anbalagan, N.; Gunasekaran, V.; Leonard, J. T. Biol. Pharm. Bull. 2004, 27, 1683-1687.
10. Maguire, M. P.; Sheets, K. R.; McVety, K.; Spada, A. P.; Zilberstein, A. J. Med. Chem. 1994, 37, 2129-2137.
11. Wilson, W. D.; Zhao, M.; Patterson, S. E.; Wydra, R. L.; Janda, L.; Strekowski, L. Med. Chem. Res. 1992, 2, 102-110.
12. Strekowski, L.; Mokrosz, J. L.; Honkan, V. A.; Czarny, A.; Cegla, M. T.; Patterson, S. E.; Wydra, R. L.; Schinazi, R. F. J. Med. Chem. 1991, 34, 1739-1746.
13. Firestone, G. L.; Sundar, S. N. Expert. Rev. Mol. Med. 2009, 11-32.
14. Lu, J. J.; Meng, L. H.; Cai, Y. J.; Chen, Q.; Tong, L. J.; Lin, L. P.; Ding, J. Cancer Biol. Ther. 2008, 7, 1017-1023.
15. Kouznetsov, V. V.; Rojas Ruíza, F. A.; Vargas Méndeza, L. Y.; Gupta, M. P. Lett. Drug Des. Discov. 2012, 9, 680-686.
16. Joule, J. A.; Mills, K. Heterocyclic Chemistry, 5th ed.; Wiley-Blackwell: Chichester, UK, 2010.
17. Hans, R. H.; Guantai, E. M.; Lategan, C.; Smith, P. J.; Wanc, B.; Franzblau, S. G.; Gut, J.; Rosenthal, P. J.; Chibale, K. Bioorg Med. Chem. Lett. 2010, 20, 942-944.
18. Maretina, I. A.; Trofimov, B. A. Russ. Chem. Rev. 2006, 75, 825-845.
19. Siddiq, A.; Dembitsky, V. Anticancer Agents Med. Chem. 2008, 8, 132-170.
20. Deng, S.; Wang, Y.; Inui, T.; Chen, S. N.; Farnsworth, N. R.; Cho, S.; Franzblau, S. G.; Pauli, G. F. Phytother. Res. 2008, 22, 878-882.
21. Tian, D.; Yan, H.; Li, H. Supramol. Chem. 2010, 22, 249-255.
22. Narayanaswamy, N.; Maity, D.; Govindaraju, T. Supramol. Chem. 2011, 23, 703-709.
23. Maity, D.; Govindaraju, T. Chem. Commun., 2012, 48, 1039-1041.
24. Kuntala, N.; Telu, J. R.; Banothu, V.; Babu, N. S.; Anireddy, J. S.; Pal, S. Med. Chem. Commun. 2015, 6, 1612-1618.
25. Wu, Y.; Pan, M.; Dai, Y.; Liu, B.; Cui, J.; Shi, W.; Qiu, Q.; Huang, W.; Qian, H. Bioorg. Med. Chem. 2016, 24, 2287-2308.
26. Ding, H.; Liu, G.; Pu, S.; Zheng, C. Dyes Pigments 2014, 103, 82-88.
27. Sahay, I. I.; Ghalsasi, P. S. Synthetic Commun. 2017, 47, 825.
28. Chereddy, N. R.; Thennarasu, S.; Mandal, A. B. Dalton T. 2012, 41, 11753-11759.
29. Chereddy, N. R.; Thennarasu, S.; Mandal, A. B. Analyst 2013, 138, 1334-1337.
30. Koleva, I. I.; Van Beek, T. A.; Linssen, J. P. H.; De Groot, A.; Evstatieva, L. N. Phytochem. Analysis 2002, 13, 8-17.
31. Ebrahimzadeh, M. A.; Pourmorad, F.; Bekhradnia, A. R. Afr. J. Biotechol. 2008, 7, 3188-3192.
32. Zhang, T. T.; Liu Y. J.; Yang, L.; Jiang, J. G.; Zhao, J. W.; Zhu, W. Med. Chem. Commun. 2017, 8, 1673-1680.
33. Anjomshoa, M.; Hadadzadeh, H.; Fatemi, S. J.; Torkzadeh-Mahani, M. Spectrochim. Acta A 2015, 136, 205-215.
34. Dundar, A.; Okumus, V.; Ozdemir, S.; Yildiz, A. Int. J. Food Prop. 2013, 16, 1105-1116.
35. Ağırtaş, M. S.; Cabir, B.; Özdemir, S.; Okumus, V.; Aslantaş, A. Chem. Select. 2017, 2, 11352-11357.
36. Oyaizu, M. Japan. J. Nutr. 1986, 44, 307-315.
37. Khan, S. A.; Asiri, A. M. J. Heterocycl. Chem. 2012, 49, 1452-1457.
38. Keypour, H.; Shooshtari, A.; Rezaeivala, M.; Kup, F. O.; Rudbari, H. A. Polyhedron 2015, 97, 75-82.