Synthesis and antioxidant activity of oxazolyl/thiazolylsulfonylmethyl pyrazoles and isoxazoles

European Journal of Medicinal Chemistry

Volumn 46, Issue 10, 2011, Pages 5034-5038

  Padmaja, A ^a   Rajasekhar, C ^a   Muralikrishna, A ^a   Padmavathi, V ^a  

^a SRI VENKATESWARA UNIVERSITY   (India)

Author keywords

Antioxidant activity; Isoxazoles; Oxazoles; Pyrazoles; Thiazoles

Indexed keywords

2 (1' PHENYL 3',5' DIARYLPYRAZOL 4' YLSULFONYLMETHYL) 4,5 DIHYDROOXAZOLE; 2 (1' PHENYL 3',5' DIARYLPYRAZOL 4' YLSULFONYLMETHYL) 4,5 DIHYDROTHIAZOLE; 2 (3' ,5' DIARYLISOXAZOL 4' YLSULFONYLMETHYL) 4,5 DIHYDROTHIAZOLE; 2 (3' ,5' DIARYLISOXAZOL 4' YLSULFONYLMETHYL)4,5 DIHYDROOXAZOLE; 2 (3',5' DIARYLISOXAZOL 4' YLSULFONYLMETHYL) 4,5 DIHYDROOXAZOLE; 2 (3',5' DIARYLISOXAZOL 4' YLSULFONYLMETHYL) 4,5 DIHYDROTHIAZOLE; 2 (4' ,5' DIHYDRO 4' ARYL 1' H PYRAZOL 3' YLSULFONYLMETHYL) 4,5 DIHYDROOXAZOLE; 2 (4' ARYL 1' H PYRAZOL 3' YLSULFONYLMETHYL) 4,5 DIHYDROOXAZOLE; 2 (4' ARYL 1'H PYRAZOL 3' YLSULFONYLMETHYL) 4,5 DIHYDROOXAZOLE; 2 (4' ARYL 1'H PYRAZOL 3' YLSULFONYLMETHYL) 4,5 DIHYDROTHIAZOLE; 2 (4' ARYL 1'HPYRAZOL 3' YLSULFONYLMETHYL) 4,5 DIHYDROTHIAZOLE; 2 (4',5' DIHYDRO 1' PHENYL 3',5' DIARYLPYRAZOL 4' YLSULFONYLMETHYL) 4,5 DIHYDROOXAZOLE; 2 (4',5' DIHYDRO 1' PHENYL 3',5' DIARYLPYRAZOL 4' YLSULFONYLMETHYL) 4,5 DIHYDROTHIAZOLE; 2 (4',5' DIHYDRO 3',5' DIARYLISOXAZOL 4' YLSULFONYLMETHYL) 4,5 DIHYDROOXAZOLE; 2 (4',5' DIHYDRO 3',5' DIARYLISOXAZOL 4' YLSULFONYLMETHYL) 4,5 DIHYDROTHIAZOLE; 2 (4',5' DIHYDRO 4' ARYL 1'HPYRAZOL 3' YLSULFONYLMETHYL) 4,5 DIHYDROTHIAZOLE; ESTER DERIVATIVE; ISOXAZOLE DERIVATIVE; OXAZOLE DERIVATIVE; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; BIOLOGY; CHEMISTRY; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTRON; IC 50;

ANTIOXIDANTS; BIPHENYL COMPOUNDS; FREE RADICALS; ISOXAZOLES; NITRIC OXIDE; OXAZOLES; PICRATES; PYRAZOLES; THIAZOLES;

EID: 80053198391     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.08.010     Document Type: Article

References (38)

1. A. Rivkin, Y.S. Cho, A.E. Gabarda, F. Yoshimura, and S.J. Danishefsky J. Nat. Prod. 67 2004 139 143
2. T. Ganesh, J.K. Schilling, R.K. Palakodety, R. Ravindra, N. Shanker, S. Bane, and D.G.I. Kingston Tetrahedron 59 2003 9979 9984
3. P.V. Plazzi, F. Bordi, M. Mor, C. Silva, G. Morini, A. Caretta, E. Barocelli, and T. Vitali Eur. J. Med. Chem. 30 1995 881 889
4. N. Bai, Y. Sha, and Ge. Meng Molecules 13 2008 943 947
5. D.J. Hu, S.F. Liu, T.H. Huang, H.Y. Tu, and A.D. Zhang Molecules 14 2009 1288 1303
6. K. Taori, V.J. Paul, and H. Luesch J. Am. Chem. Soc. 130 2008 1806 1807
7. A.T. Fuller Nature 175 1955 722
8. F. Sasse, H. Steinmetz, G. Hôfle, and H. Reichenbach J. Antibiot. 56 2003 520 525
9. S. Kehraus, G.M. Konig, and A.D. Wright J. Org. Chem. 67 2002 4989 4992
10. K. Gerth, N. Bedorf, G. Hofle, H. Irschik, and H. Reichenbach J. Antibiot. 49 1996 560 563
11. H. Umezawa, K. Maeda, T. Takeuchi, and Y. Okami J. Antibiot. 19 1966 200 209
12. B. Silakowski, H.U. Schairer, H. Ehret, B. Kunze, S. Weinig, G. Nordsiek, P. Brandt, H. Blocker, G. Hofle, S. Beyer, and R. Muller J. Biol. Chem. 274 1999 37391 37399
13. H. Abe, T. Takaishi, T. Okuda, K. Aoe, and T. Date Tetrahedron Lett. 19 1978 2791 2794
14. M.F. Earle, and R.I. Glazer Cancer Res. 43 1983 133 137
15. D.N. Carney, G.S. Ahluwalia, H.N. Jayaram, D.A. Cooney, and D.G. Johns J. Clin. Invest. 75 1985 175
16. G.J. Tricot, H.N. Jayaram, C.R. Nichols, K. Pennington, E. Lapis, G. Weber, and R. Hoffman Cancer Res. 47 1997 4988 4991
17. G. Weber, U.S. Pat. 5, 405 (1995) 837.
18. K.D. Shin, M.-Y. Lee, D.-S. Shin, S. Lee, K.-H. Son, S. Koh, Y.-K. Paik, B.-M. Kwon, and D.C. Han J. Biol. Chem. 280 2005 41439 41448
19. F.A.K. Amer, M. Hammouda, A.A.S. El-Ahl, and B.F. Abdel-Wahab J. Chin. Chem. Soc. 54 2007 1543 1552
20. A.O. Abdolhamid, A.H. El-Ghandour, and A.A.M. El-Reedy J. Chin. Chem. Soc. 55 2008 406 413
21. M. Sechi, L. Sannia, F. Carta, M. Palomba, R. Dallocchio, A. Dessi, M. Derudas, Z. Zawahir, and N. Neamati Antivir. Chem. Chemother. 16 2005 41 61
22. S. Rapposelli, A. Lapucci, F. Minutolo, E. Orlandini, G. Ortore, M. Pinza, and A. Balsamo Farmaco 59 2004 25 31
23. B. Cottineau, P. Toto, C. Marot, A. Pipaud, and J. Chenault Bioorg. Med. Chem. Lett. 12 2002 2105 2108
24. P. Cali, L. Naerum, S. Mukhija, and A. Hjelmencrantz Bioorg. Med. Chem. Lett. 14 2004 5997 6000
25. S. Shinde, W. Jadhav, R. Pawar, and S. Bhusare J. Chin. Chem. Soc. 51 2004 775 778
26. F. Al-Omran, and A.A. El-Khair J. Heterocycl. Chem. 41 2004 327 333
27. T.D. Penning, J.J. Talley, S.R. Bertenshaw, J.S. Carter, P.W. Collins, S. Docter, M.J. Graneto, L.F. Lee, J.W. Malecha, J.M. Miyashiro, R.S. Rogers, D.J. Rogier, S.S. Yu, G.D. Anderson, E.G. Burton, J.N. Cogburn, S.A. Gregory, C.M. Koboldt, W.E. Perkins, K. Seibert, A.W. Veenhuizen, Y.Y. Zhang, and P.C. Isakson J. Med. Chem. 40 1997 1347 1365
28. X. Deng, and N.S. Mani Org. Lett. 10 2008 1307 1310
29. A.R. Katritzky, M. Wang, S. Zhang, and M.V. Voronkov J. Org. Chem. 66 2001 6787 6791
30. J. Elguero A.R. Katritzky, C.W. Rees, EF.V. Scriven, Comprehensive Heterocyclic Chemistry II vol. 3 1996 Pergamon Oxford 1 75
31. X. Deng, and N.S. Mani Org. Lett. 8 2006 3505 3508
32. T. Ichiba, W.Y. Yoshida, P.J. Scheuer, T. Higa, and D.G. Gravalos J. Am. Chem. Soc. 113 1991 3173 3174
33. D. Bhaskar Reddy, M. Muralidhar Reddy, and G.V. Subbaraju Indian J. Chem. 34B 1995 816 822
34. M. Burits, and F. Bucar Phytother Res. 14 2000 323 328
35. M. Cuendet, K. Hostettmann, and O. Potterat Helv. Chim. Acta 80 1997 1144 1152
36. L.C. Green, D.A. Wagner, J. Glogowski, P.L. Skipper, and J.K.S.R. Wishnok Anal. Biochem. 126 1982 131 136
37. L. Marcocci, J.J. Maguire, M.T. Droy-Lefaix, and L. Packer Biochem. Biophys. Res. Commun. 201 1994 748 755
38. R.J. Ruch, S.J. Cheng, and J.E. Klaunig Carcinogenesis 10 1989 1003 1008