Synthesis, antioxidant and anticholinesterase activities of novel coumarylthiazole derivatives

Bioorganic Chemistry

Volumn 59, Issue , 2015, Pages 80-90

  Kurt, Belma Zengin ^a   Gazioglu, Isil ^a   Sonmez, Fatih ^b   Kucukislamoglu, Mustafa ^b  

^a BEZMIALEM VAKIF UNIVERSITY   (Turkey)

^b SAKARYA UNIVERSITY   (Turkey)

Author keywords

Acetylcholinesterase; Antioxidant; Butyrylcholinesterase; Coumarin; Thiazole

Indexed keywords

1 (2 FLUOROPHENYL) 3 [4 (2 OXO 2H CHROMEN 3 YL)THIAZOL 2 YL]UREA; 1 (2 METHOXYPHENYL) 3 [4 (2 OXO 2H CHROMEN 3 YL)THIAZOL 2 YL]UREA; 1 (3 CHLOROPHENYL) 3 [4 (2 OXO 2H CHROMEN 3 YL)THIAZOL 2 YL]UREA; 1 (3 FLUOROPHENYL) 3 [4 (2 OXO 2H CHROMEN 3 YL)THIAZOL 2 YL]UREA; 1 (3 METHOXYPHENYL) 3 [4 (2 OXO 2H CHROMEN 3 YL)THIAZOL 2 YL]UREA; 1 (4 BROMOPHENYL) 3 [4 (2 OXO 2H CHROMEN 3 YL)THIAZOL 2 YL]UREA; 1 (4 CHLOROPHENYL) 3 [4 (2 OXO 2H CHROMEN 3 YL)THIAZOL 2 YL]UREA; 1 (4 FLUOROPHENYL) 3 [4 (2 OXO 2H CHROMEN 3 YL)THIAZOL 2 YL]UREA; 1 (4 FLUOROPHENYL) 3 [4 (6 NITRO 2 OXO 2H CHROMEN 3 YL)THIAZOL 2 YL]UREA; 1 (4 IODOPHENYL) 3 [4 (2 OXO 2H CHROMEN 3 YL)THIAZOL 2 YL]UREA; 1 (4 METHOXYPHENYL) 3 [4 (2 OXO 2H CHROMEN 3 YL)THIAZOL 2 YL]UREA; 1 (4 NITROPHENYL) 3 [4 (2 OXO 2H CHROMEN 3 YL)THIAZOL 2 YL]UREA; 1 (4 TOLYL) 3 [4 (2 OXO 2H CHROMEN 3 YL)THIAZOL 2 YL]UREA; 1 PHENYL 3 [4 (2 OXO 2H CHROMEN 3 YL)THIAZOL 2 YL]UREA; 1 [4 (8 METHOXY 2 OXO 2H CHROMEN 3 YL)THIAZOL 2 YL] 3 (3 METHOXYPHENYL)UREA; 1 [4 (8 METHOXY 2 OXO 2H CHROMEN 3 YL)THIAZOL 2 YL] 3 (4 CHLOROPHENYL)THIOUREA; 1 [4 (8 METHOXY 2 OXO 2H CHROMEN 3 YL)THIAZOL 2 YL] 3 (4 METHOXYPHENYL)UREA; 1 [4 (8 METHOXY 2 OXO 2H CHROMEN 3 YL)THIAZOL 2 YL] 3 (4 TOLYL)UREA; ACETYLCHOLINESTERASE; ANTIOXIDANT; CHOLINESTERASE; CHOLINESTERASE INHIBITOR; COUMARYLTHIAZOLE DERIVATIVE; DONEPEZIL; GALANTAMINE; QUERCETIN; RIVASTIGMINE; TACRINE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; COUMARIN DERIVATIVE; UREA;

ANTIOXIDANT ACTIVITY; ANTIOXIDANT ASSAY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHOLINESTERASE INHIBITION; DRUG SYNTHESIS; IC50; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; ANALOGS AND DERIVATIVES; ANIMAL; CHEMISTRY; ELECTROPHORUS; HORSE; METABOLISM; SYNTHESIS;

ACETYLCHOLINESTERASE; ANIMALS; ANTIOXIDANTS; BUTYRYLCHOLINESTERASE; CHOLINESTERASE INHIBITORS; COUMARINS; ELECTROPHORUS; HORSES; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLES; UREA;

EID: 84923280570     PISSN: 00452068     EISSN: 10902120     Source Type: Journal    
DOI: 10.1016/j.bioorg.2015.02.002     Document Type: Article

References (44)

1. O. di Pietro, E. Viayna, E.V. Garcia, M. Bartolini, R. Ramon, J.J. Jimenez, M.V. Clos, B. Perez, V. Andrisano, F.J. Luque, R. Lavilla, and D.M. Torrero Eur. J. Med. Chem. 73 2014 141 152
2. P.M. Ruiz, L. Rubio, E.G. Palomero, I. Dorronsoro, M.M. Millan, R. Valenzuela, P. Usan, C. de Austria, M. Bartolini, V. Andrisano, A.B. Chanal, M. Orozco, F.J. Luque, M. Medina, and A. Martinez J. Med. Chem. 48 2005 7223 7233
3. M. Ignasik, M. Bajda, N. Guzior, M. Prinz, U.l. Holzgrabe, and B. Malawska Arch. Pharm. Chem. Life Sci. 345 2012 509 516
4. F.C. Meng, F. Mao, W.J. Shan, F. Qin, L. Huang, and X.S. Li Bioorg. Med. Chem. Lett. 22 2012 4462 4466
5. Q. Yu, H.W. Holloway, T. Utsuki, A. Brossi, and N.H. Greig J. Med. Chem. 42 1999 1855 1861
6. Z.P. Wu, X.W. Wu, T. Shen, Y.P. Li, X. Cheng, L.Q. Gu, Z.S. Huang, and L.K. An Arch. Pharm. Chem. Life Sci. 345 2012 175 184
7. N. Chitranshi, S. Gupta, P.K. Tripathi, and P.K. Seth Med. Chem. Res. 22 2013 2328 2345
8. S.S. Xie, X.B. Wang, J.Y. Li, L. Yang, and L.Y. Kong Eur. J. Med. Chem. 64 2013 540 553
9. W.J. Shan, L. Huang, Q. Zhou, F.C. Meng, and X.S. Li Eur. J. Med. Chem. 46 2011 5885 5893
10. P. Camps, R. el Achab, D.M. Gorbig, J. Morral, D.M. Torrero, A. Badia, J.E. Banos, N.M. Vivas, X. Barril, M. Orozcor, and F.J. Luque J. Med. Chem. 42 1999 3227 3242
11. F. Leonetti, M. Catto, O. Nicolotti, L. Pisani, A. Cappa, A. Stefanachi, and A. Carotti Bioorg. Med. Chem. 16 2008 7450 7456
12. M. Pohanka Expert Opin. Ther. Pat. 22 2012 871 886
13. S.F. Razavi, M. Khoobi, H. Nadri, A. Sakhteman, A. Moradi, S. Emami, A. Foroumadi, and A. Shafiee Eur. J. Med. Chem. 64 2013 252 259
14. J.L. Sussman, M. Harel, F. Frolow, C. Oefner, A. Goldman, L. Toker, and I. Silman Science 253 1991 872 879
15. A. Mary, D.Z. Renko, C. Guillou, and C. Thal Bioorg. Med. Chem. 6 1998 1835 1850
16. A. Asadipour, M. Alipour, M. Jafari, M. Khoobi, S. Emami, H. Nadri, A. Sakhteman, A. Moradi, V. Sheibani, F.H. Moghadam, A. Shafiee, and A. Foroumadi Eur. J. Med. Chem. 70 2013 623 630
17. A. Samadi, M.F. Revenga, C. Perez, I. Iriepa, I. Moraleda, M.I.R. Franco, and J.M. Contelles Eur. J. Med. Chem. 67 2013 64 74
18. J.T. Ferrara, L.M. Cano, and M.E. Fonseca Bioorg. Med. Chem. Lett. 13 2003 1825 1827
19. M.L. Bolognesi, A. Cavalli, L. Valgimigli, M. Bartolini, M. Rosini, V. Andrisano, M. Recanatini, and C. Melchiorre J. Med. Chem. 50 2007 6446 6449
20. B. Tasso, M. Catto, O. Nicolotti, F. Novelli, M. Tonelli, I. Giangreco, L. Pisani, A. Sparatore, V. Boido, A. Carotti, and F. Sparatore Eur. J. Med. Chem. 46 2011 2170 2184
21. S.O. Nam, D.H. Park, Y.H. Lee, J.H. Ryu, and Y.S. Lee Bioorg. Med. Chem. 22 2014 1262 1267
22. A. Kumar, M.H. Gupta, and M. Kumar Tetrahedron Lett. 52 2011 4521 4525
23. A. Parvez, J. Meshram, V. Tiwari, J. Sheik, R. Dongre, M.H. Youssoufi, and T. Hadda Eur. J. Med. Chem. 45 2010 4370 4378
24. P. Anand, B. Singh, and N. Singh Bioorg. Med. Chem. 20 2012 1175 1180
25. J.L. Vidaluc, F. Calmel, D.C. Bigg, E. Carilla, and M. Briley J. Med. Chem. 38 1995 2969 2973
26. V. Lakshmi, V.S. Kannan, and R. Boopathy J. Mol. Graph. Model. 40 2013 72 79
27. F. Sonmez, S. Sevmezler, A. Atahan, M. Ceylan, D. Demir, N. Gencer, O. Arslan, and M. Kucukislamoglu Bioorg. Med. Chem. Lett. 21 2011 7479 7482
28. N. Gencer, D. Demir, F. Sonmez, and M. Kucukislamoglu Bioorg. Med. Chem. 20 2012 2811 2821
29. F. Sonmez, C. Bilen, S. Sumersan, N. Gencer, S. Isik, O. Arslan, and M. Kucukislamoglu J. Enzyme Inhib. Med. Chem. 29 2014 118 123
30. N. Gencer, F. Sonmez, D. Demir, O. Arslan, and M. Kucukislamoglu Curr. Topics Med. Chem. 14 2014 1450 1462
31. N.N. Karade, S.V. Gampawar, S.V. Shinde, and W.N. Jadhav Chin. J. Chem. 25 2007 1686 1689
32. G.L. Ellman, K.D. Courtney, V. Andres, and R.M. Featherstone Biochem. Pharmacol. 7 1961 88 95
33. I.W. Wyman, and D.H. Macartney J. Org. Chem. 74 2009 8031 8038
34. Y. Chen, L. Fang, S. Peng, H. Liao, J. Lehmann, and Y. Zhang Bioorg. Med. Chem. Lett. 22 2012 3181 3187
35. W. Luo, Y.B. Su, C. Hong, R.G. Tian, L.P. Su, Y.Q. Wang, Y. Li, J.J. Yue, and C.J. Wang Bioorg. Med. Chem. 21 2013 7275 7282
36. S. Thiratmatrakul, C. Yenjai, P. Waiwut, O. Vajragupta, P. Reubroycharoen, M. Tohda, and C. Boonyarat Eur. J. Med. Chem. 75 2014 21 30
37. T. Mohamed, W. Osman, G. Tin, and P.P.N. Rao Bioorg. Med. Chem. Lett. 23 2013 4336 4341
38. B. Kaboudin, M. Arefi, S. Emadi, and V.S. Hasani Bioorg. Chem. 41-42 2012 22 27
39. P. Anand, and B. Singh Med. Chem. Res. 22 2013 1648 1659
40. H.R. Girisha, J.N.N.S. Chandra, S. Boppana, M. Malviya, C.T. Sadashiva, and K.S. Rangappa Eur. J. Med. Chem. 44 2009 4057 4062
41. R. Re, N. Pellegrini, A. Proteggente, A. Pannala, M. Yang, and C.R. Evans Free Radical Bio. Med. 26 1999 1231 1237
42. R. Apak, K. Guclu, M. Ozyurek, and S.E. Karademir J. Agric. Food Chem. 52 2004 7970 7981
43. C.F. Koelsch J. Am. Chem. Soc. 72 1950 2993 2995
44. O.I. Zhuravel, S.M. Kovalenko, S.V. Vlasov, and V.P. Chernykh Molecules 10 2005 444 456