Synthesis, hypoglycemic and hypolipidemic activities of novel thiazolidinedione derivatives containing thiazole/triazole/oxadiazole ring

European Journal of Medicinal Chemistry

Volumn 53, Issue , 2012, Pages 308-315

  Mohammed Iqbal, A K ^a   Khan, Ashraf Y ^a   Kalashetti, Mallikarjun B ^a   Belavagi, Ningaraddi S ^a   Gong, Young Dae ^b   Khazi, Imitiyaz Ahmed M ^a  

^a KARNATAK UNIVERSITY   (India)

^b Dongguk University   (South Korea)

Author keywords

Hypoglycemic activity; Hypolipidemic activity; Pioglitazone analogs; Thiazolidinediones

Indexed keywords

2,4 THIAZOLIDINEDIONE DERIVATIVE; 4 (2 METHYL THIAZOL 4 YLMETHOXY)BENZALDEHYDE; 4 (2 PHENYL THIAZOL 4 YLMETHOXY)BENZALDEHYDE; 4 [2 [(5 BENZYL 1,3,4 OXADIAZOLE 2 YL)THIO]ETHOXY]BENZALDEHYDE; 4 [2 [(5 BENZYL 4H 1,2,4 TRIAZOL 3 YL)THIO]ETHOXY]BENZALDEHYDE; 4 [2 [(5 PHENYL 1,3,4 OXADIAZOL 2 YL)THIO]ETHOXY]BENZALDEHYDE; 4 [2 [(5 PHENYL 4H 1,2,4 TRIAZOL 3 YL)THIO]ETHOXY]BENZALDEHYDE; 4 [2 [(5 PYRIDIN 4 YL 1,3,4 OXADIAZOL 2 YL)THIO]ETHOXY]BENZALDEHYDE; 4 [2 [[5 (2 NITROPHENYL) 4H 1,2,4 TRIAZOL 3 YL]THIO]ETHOXY]BENZALDEHYDE; 4 [2 [[5 (4 BROMOPHENYL) 4H 1,2,4 TRIAZOL 3 YL]THIO]ETHOXY]BENZALDEHYDE; 4 [2 [[5 (4 CHLOROPHENYL) 4H 1,2,4 TRIAZOL 3 YL]THIO]ETHOXY]BENZALDEHYDE; 4 [2 [[5 (4 METHYLPHENYL) 4H 1,2,4 TRIAZOL 3 YL]THIO]ETHOXY]BENZALDEHYDE; 4 [2 [[5 (4 METOXYPHENYL) 4H 1,2,4 TRIAZOL 3 YL]THIO]ETHOXY]BENZALDEHYDE; 4 [2 [[5 (4 NITROPHENYL) 4H 1,2,4 TRIAZOL 3 YL]THIO]ETHOXY]BENZALDEHYDE; 5 [4 (2 METHYL THIAZOL 4 YLMETHOXY)BENZYLIDENE]THIAZOLIDINE 2,4 DIONE; 5 [4 (2 PHENYL THIAZOL 4 YLMETHOXY)BENZYLIDENE]THIAZOLIDINE 2,4 DIONE; 5 [4 [2 [(5 BENZYL 1,3,4 THIADIAZOL 2 YL)THIO]ETHOXY]BENZYLIDENE] 1,3 THIAZOLIDINE 2,4 DIONE; 5 [4 [2 [(5 BENZYL 4H 1,2,4 TRIAZOL 3 YL)THIO]ETHOXY]BENZYLIDENE]1,3 THIAZOLIDINE 2,4 DIONE; 5 [4 [2 [(5 PHENYL 1,3,4 OXADIAZOL 2 YL)THIO]ETHOXY]BENZYLIDENE] 1,3 THIAZOLIDINE 2,4 DIONE; 5 [4 [2 [(5 PHENYL 4H 1,2,4 TRIAZOL 3 YL)THIO]ETHOXY]BENZYLIDENE]1,3 THIAZOLIDINE 2,4 DIONE; 5 [4 [2 [(5 PYRIDIN 3 YL 1,3,4 OXADIAZOL 2 YL)THIO]ETHOXY]BENZYLIDENE] 1,3 THIAZOLIDINE 2,4 DIONE; 5 [4 [2 [[5 (2 NITRO PHENYL) 4H 1,2,4 TRIAZOL 3 YL]THIO]ETHOXY]BENZYLIDENE] 1,3 THIAZOLIDINE 2,4 DIONE; 5 [4 [2 [[5 (4 BROMO PHENYL) 4H 1,2,4 TRIAZOL 3 YL]THIO]ETHOXY]BENZYLIDENE] 1,3 THIAZOLIDINE 2,4 DIONE; 5 [4 [2 [[5 (4 CHLORO PHENYL) 4H 1,2,4 TRIAZOL 3 YL]THIO]ETHOXY]BENZYLIDENE] 1,3 THIAZOLIDINE 2,4 DIONE; 5 [4 [2 [[5 (4 METHOXYPHENYL) 4H 1,2,4 TRIAZOL 3 YL]THIO]ETHOXY]BENZYLIDENE] 1,3 THIAZOLIDINE 2,4 DIONE; 5 [4 [2 [[5 (4 METHYLPHENYL) 4H 1,2,4 TRIAZOL 3 YL]THIO]ETHOXY]BENZYLIDENE] 1,3 THIAZOLIDINE 2,4 DIONE; 5 [4 [2 [[5 (4 NITRO PHENYL) 4H 1,2,4 TRIAZOL 3 YL]THIO]ETHOXY]BENZYLIDENE] 1,3 THIAZOLIDINE 2,4 DIONE; ANTIDIABETIC AGENT; ANTILIPEMIC AGENT; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIDIABETIC ACTIVITY; ARTICLE; CONTROLLED STUDY; DIABETES MELLITUS; DRUG ACTIVITY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; GLUCOSE BLOOD LEVEL; HYPOLIPIDEMIC ACTIVITY; MALE; NONHUMAN; RAT; SUBSTITUTION REACTION; TRIACYLGLYCEROL BLOOD LEVEL;

ANIMALS; CHEMISTRY TECHNIQUES, SYNTHETIC; DIABETES MELLITUS, EXPERIMENTAL; HYPOGLYCEMIC AGENTS; HYPOLIPIDEMIC AGENTS; MALE; OXADIAZOLES; RATS; RATS, WISTAR; THIAZOLES; THIAZOLIDINEDIONES; TRIAZOLES;

EID: 84861611610     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.04.015     Document Type: Article

References (29)

1. I. Isseman, and S. Green Nature 347 1990 645 650
2. D.J. Mangelsdorf, and R.M. Evans Cell 83 1995 841 850
3. T.M. Willson, P.J. Brown, D.D. Sternbach, and B.R. Henke J. Med. Chem. 43 2000 527 550
4. I. Bogacka, H. Xie, G.A. Bray, and S.R. Smith Diabetes Care 27 2004 1660 1667
5. T.M. Willson, J.E. Cobb, D.J. Cowan, R.W. Wiethe, I.D. Correa, S.R. Prakash, K.D. Beck, L.B. Moore, S.A. Liewer, and J.M. Lehmann J. Med. Chem. 39 1996 665 668
6. V. Ribon, J.H. Johnson, H.S. Camp, and A.R. Saltiel Proc. Natl. Acad. Sci. U.S.A 95 1998 14751 14756
7. R.W. Nesto, D. Bell, R.O. Bonow, V. Fonseca, S.M. Grundy, E.S. Horton, M.L. Winter, D. Porte, C.F. Semenkovich, S. Smith, L.H. Young, and R. Kahn Diabetes Care 27 2004 256 263
8. H. Yki-Järvinen, and N. Eng J. Med. 351 2004 1106 1118
9. F.E. Hooper, and T.B. Johnson J. Am. Chem. Soc. 56 1984 484 485
10. W.S. Hinegardner, and T.B. Johnson J. Am. Chem. Soc. 52 1930 3742 3746
11. E. Hoggarth J. Chem. Soc. 1949 1163 1167
12. E. Hoggarth J. Chem. Soc. 1949 1918 1923
13. F. Kurzer J. Chem. Soc. 1971 2927 2931
14. E. Hoggarth J. Chem. Soc. 1952 4811 4817
15. R.W. Young, and K.H. Wood J. Am. Chem. Soc. 77 1955 400 403
16. C. Ainsworth J. Am. Chem. Soc. 78 1956 4475 4478
17. R. Laudien, I. Yoshida, and T. Nagamura J. Chem. Soc. Perkin Trans. 2 2002 1772 1777
18. V. Patil, K. Tilekar, S. Mehendale-Munj, R. Mohan, and C.S. Ramaa Eur. J. Med. Chem. 45 2010 4539 4544
19. Y. Momose, K. Meguro, H. Ikeda, C. Hatanaka, S. Oi, and T. Sohda Chem. Pharm. Bull. 39 6 1991 1440 1445
20. L.F.C. Costa Leite, R.H. Veras Mourao, M.C. Alves de Lima, S.L. Galdino, M.Z. Hernandes, F.A. Rocha Neves, S. Vidal, J. Barbe, and I.R. Pitta Eur. J. Med. Chem. 42 2007 1263 1271
21. V.L.M. Guarda, M.A. Pereira, C.A. De Simone, J.C. Albuquerque, S.L. Galdino, J. Chantegrel, M. Perrissin, C. Beney, F. Thomasson, I.R. Pitta, and C. Luu-Duc Sulfur Lett. 26 2003 17 27
22. S.F. Tan, K.P. Ang, and Y.F. Fong J. Chem. Soc. Perkin Trans. II 1986 1941 1944
23. J.F.C. Albuquerque, A. Albuquerque, C.C. Azevedo, F. Thomasson, S.L. Galdino, J. Chantegrel, M.T.J. Catanho, I.R. Pitta, and C. Luu-Duc Pharmazie 50 1995 387 389
24. W. Heng, S. Tieu, Hautmann, K. Kuan, D.S. Pedersen, M. Pietsch, M. Gütschow, and A.D. Abell Bioorg. Med. Chem. 19 2011 7453 7463
25. T. Ishida, Y. In, M. Inoue, Y. Ueno, C. Tanaka, N. Hamanaka, 30 (1989) 959-962.
26. R. Murugan, S. Anbazhagan, and S.S. Narayanan Eur. J. Med. Chem. 44 2009 3272 3279
27. A.St.G. Hugget, and D.A. Nixon The Lancet 270 1957 368 370
28. J.S. Annino Clinical Chemistry: Principles and Procedures fourth ed. 1976 Little Brown and Company Boston 184-188
29. C.S. Frings, T.W. Fendley, R.T. Dunn, and C.A. Queen Clin. Chem. 18 1972 673 674