Arif KIVRAK, Halil KOCA, Jeger Ali OAGAZ, Can YILMAZ, Selahattin AYDEMİR, Metin KONUŞ

Synthesis and biological properties of novel 1-methyl-2-(2-(prop-2-yn-1-yloxy)benzylidene) hydrazine analogues

1-Methyl-2-(2-(prop-2-yn-1-yloxy)benzylidene)hydrazine analogues were readily prepared in good yields by the reaction of 2-(prop-2-yn-1-yloxy)benzaldehydes and methyl hydrazine. The reaction tolerates a variety of substituents on the 2-hydroxybenzaldehyde to form nitro-, halo-, methoxy-, and naphthyl-substituted 1-methyl-2-(2-(prop-2-yn-1- yloxy)benzylidene)hydrazines. The in vitro antioxidant capacity measurements revealed that among all the analyzed hydrazine analogues that surpassed the Trolox standard, 1-(2-(but-3-ynyl)-5-nitrobenzylidene)-2-methylhydrazine had the maximum value, which was approximately 1.7 times that of Trolox.

PDF

___

1. Yang, Y.; Gao, C. Y.; Liu, J. L.; Dong, D. W. Anal. Methods 2016, 8, 2863-2871.
2. Tatum, L. A.; Su, X.; Aprahamian, I. Acc. Chem. Res. 2014, 47, 2141-2149.
3. Mohanraj, M.; Ayyannan, G.; Raja, G.; Jayabalakrishnan, C. Mat. Sci. Eng. C-Mater. 2016, 69, 1297-1306.
4. Le Goff, G.; Ouazzani, J. Bioorg. Med. Chem. 2014, 22, 6529-6544.
5. Werengowska-Ciecwierz, K.; Wisniewski, M.; Terzyk, A. P.; Furmaniak, S. Adv. Cond. Matter Phys. 2015; 619 : 219-222.
6. Zora, M.; Kivrak, A. J. Org. Chem. 2011, 76, 9379-9390.
7. Zora, M.; Kivrak, A.; Yazici, C. J. Org. Chem. 2011, 76, 6726-6742.
8. Zora, M.; Demirci, D.; Kivrak, A.; Kelgokmen, Y. Tetrahedron Lett. 2016, 57, 993-997.
9. Su, X.; Aprahamian, I. Chem. Soc. Rev. 2014, 43, 1963-1981.
10. Rhoda, H. M.; Chanawanno, K.; King, A. J.; Zatsikha, Y. V.; Ziegler, C. J.; Nemykin, V. N. Chem.-Eur. J. 2015, 21, 18043-18046.
11. Maia, R. D.; Tesch, R.; Fraga, C. A. M. Expert Opin. Ther. Pat. 2014, 24, 1161-1170.
12. Lane, D. J. R.; Mills, T. M.; Shafie, N. H.; Merlot, A. M.; Moussa, R. S.; Kalinowski, D. S.; Kovacevic, Z.; Richardson, D. R. BBA-Rev. Cancer 2014, 1845, 166-181.
13. Narang, R.; Narasimhan, B.; Sharma, S. Curr. Med. Chem. 2012, 19, 569-612.
14. Bingul, M.; Tan, O.; Gardner, C. R.; Sutton, S. K.; Arndt, G. M.; Marshall, G. M.; Cheung, B. B.; Kumar, N.; Black, D. S. Molecules 2016, 21 : E916.
15. Enders, D.; Lochtman, R.; Raabe, G. Synlett 1996, 2, 126-128.
16. Fries, S.; Pytkowicz, J.; Brigaud, T. Tetrahedron Lett. 2005, 46, 4761-4764.
17. Cere, V.; Peri, F.; Pollicino, S.; Ricci, A. Synlett 1999, 10, 1585-1587.
18. Altintop, M. D.; Ozdemir, A.; Turan-Zitouni, G.; Ilgin, S.; Atli, O.; Iscan, G.; Kaplancikli, Z. A. Euro. J. Med. Chem. 2012, 58, 299-307.
19. Coa, J. C.; Castrillon, W.; Cardona, W.; Carda, M.; Ospina, V.; Munoz, J. A.; Velez, I. D.; Robledo, S. M. Euro. J. Med. Chem. 2015, 101, 746-753.
20. Kaplanek, R.; Havlik, M.; Dolensky, B.; Rak, J.; Dzubak, P.; Konecny, P.; Hajduch, M.; Kralova, J.; Kral, V. Bioorg. Med. Chem. 2015, 23, 1651-1659.
21. Enders, D.; Schankat, J.; Klatt, M. Synlett 1994, 10, 795-797.
22. Gurkok, G.; Altanlar, N.; Suzen, S. Chemotherapy 2009, 55, 15-19.
23. Shirinzadeh, H.; Altanlar, N.; Yucel, N.; Ozden, S.; Suzen, S. Z. Naturforsch. C 2011, 66, 340-344.
24. Wang, H.; Ren, S. X.; He, Z. Y.; Wang, D. L.; Yan, X. N.; Feng, J. T.; Zhang, X. Int. J. Mol. Sci. 2014, 15, 4257-4272.
25. Cocco, M. T.; Congiu, C.; Lilliu, V.; Onnis, V. Bioorg. Med. Chem. 2006, 14, 366-372.
26. Montenegro, R. C.; Lotufo, L. V.; de Moraes, M. O.; Pessoa, C. D.; Rodrigues, F. A. R.; Bispo, M. D. F.; Cardoso, L. N. D.; Kaiser, C. R.; de Souza, M. V. N. Med. Chem. 2011, 7, 599-604.
27. Navidpour, L.; Shafaroodi, H.; Saeedi-Motahar, G.; Shafiee, A. Med. Chem. Research 2014, 23, 2793-2802.
28. Rajitha, G.; Saideepa, N.; Praneetha, P. Indian J. Chem. B 2011, 50, 729-733.
29. Sondhi, S. M.; Dinodia, M.; Kumar, A. Bioorg. Med. Chem. 2006, 14, 4657-4663.
30. Onnis, V.; Demurtas, M.; Deplano, A.; Balboni, G.; Baldisserotto, A.; Manfredini, S.; Pacifico, S.; Liekens, S.; Balzarini, J. Molecules 2016, 21 : E579.
31. Pathak, R. B.; Chovatia, P. T.; Parekh, H. H. Bioorg. Med. Chem. Lett. 2012, 22, 5129-5133.
32. Pinheiro, A. C.; Kaiser, C. R.; Nogueira, T. C. M.; Carvalho, S. A.; da Silva, E. F.; Feitosa, L. D.; Henriques, M.; Candea, A. L. P.; Lourenco, M. C. S.; de Souza, M. V. N. Med. Chem. 2011, 7, 611-623.
33. Sonar, V. N.; Crooks, P. A. J. Enzy. Inhib. Med. Chem. 2009, 24, 117-124.
34. Liu, Y. F.; Teng, Q.; Hu, J. F.; Sun, R. F.; Zhang, H. Sensor. Actuat. B-Chem. 2016, 234, 680-690.
35. Rollas, S.; Kucukguzel, S. G. Molecules 2007, 12, 1910-1939.
36. Serafini, M.; Del Rio, D. Redox Rep. 2004, 9, 145-152.
37. MacDonald-Wicks, L. K.; Wood, L. G.; Garg, M. L. J. Sci. Food Agr. 2006, 86, 2046-2056.
38. Rodrigo, J.; Fernandez, A. P.; Serrano, J.; Peinado, M. A.; Martinez, A. Free Radic. Biol. Med. 2005, 39, 26-50.
39. Sato, M.; Bremner, I. Free Radic. Biol. Med. 1993, 14, 325-337.
40. Cano, A.; Acosta, M.; Arnao, M. B. Redox Rep. 2000, 5, 365-370.
41. Dawidowicz, A. L.; Olszowy, M. Euro. Food Res. Tech. 2013, 236, 1099-1105.
42. Rahmouni, A.; Souiei, S.; Belkacem, M. A.; Romdhane, A.; Bouajila, J.; Ben Jannet, H. Bioorg. Chem. 2016, 66, 160-168.
43. Montagnat, O. D.; Lessene, G.; Hughes, A. B. Tetrahedron Lett. 2006, 47, 6971-6974.
44. Kivrak, A.; Larock, R. C. J. Org. Chem. 2010, 75, 7381-7387.
45. Schroder, H.; Haslinger, E. Magn. Reson. Chem. 1994, 32, 12-15.
46. Khoshkholgh, M. J.; Balalaie, S.; Gleiter, R.; Rominger, F. Tetrahedron 2008, 64, 10924-10929.
47. Vedachalam, S.; Wong, Q. L.; Maji, B.; Zeng, J.; Ma, J. M.; Liu, X. W. Adv. Synth. Catal. 2011, 353, 219-225.
48. Re, R.; Pellegrini, N.; Proteggente, A.; Pannala, A.; Yang, M.; Rice-Evans, C. Free Radic. Biol. Med. 1999, 26, 1231-1237.