Trisubstituted thiophene analogues of 1-thiazolyl-2-pyrazoline, super oxidase inhibitors and free radical scavengers

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 1, 2013, Pages 365-372

  Mandawad, Gajanan G ^a   Dawane, Bhaskar S ^a   Beedkar, Supriya D ^a   Khobragade, Chandrahas N ^a   Yemul, Omprakash S ^a  

^a SWAMI RAMANAND TEERTH MARATHWADA UNIVERSITY   (India)

Author keywords

Free radical scavengers; Green synthesis; PEG 400; Superoxide inhibitors; Thiophenyl thiazolyl pyrazoline

Indexed keywords

1 ACETYL 3,5 DIARYL 4,5 DIHYDRO 1H PYRAZOLE DERIVATIVE; 1 THIAZOLYL 2 PYRAZOLINE; 1 THIAZOLYL 2 PYRAZOLINE DERIVATIVE; 2 AMINO 4 HYDROXY 6 HYDROXYMETHYL PTERIDIN; 2 BUTYL 4 CHLORO 5 (1 (4 (4 CHLOROPHENYL)THIAZOL 2 YL) 3 (2,5 DICHLOROTHIOPHEN 3 YL) 4,5 DIHYDRO 1H PYRAZOL 5 YL) 1H IMIDAZOLE; 3 (2 (BENZYLTHIO) 5 CHLOROTHIOPHEN 3 YL) 5 (4 CHLOROPHENYL) 1 (4 (4 CHLOROPHENYL)THIAZOL 2 YL) 4,5 DIHYDRO 1H PYRAZOLE; 3 (4 PHENYLTHIAZOL 2 YL)PYRIDINE; 3 [5 (2 BUTYL 5 CHLORO 3H IMIDAZOL 4 YL) 1 [4 (4 CHLOROPHENYL) THIAZOL 2 YL] 4,5 DIHYDRO 1H PYRAZOL 3 YL] 5 CHLOROTHIOPHENE 2 SULFONAMIDE; 3 HYDROXY 1 NITROPHENYL 1H PYRAZOLO [4,3]PYRIDINE; 4,5 DIHYDROPYRAZOLE 1 CARBOTHIOAMIDE; 5 (3 (2 (BENZYLTHIO) 5 CHLOROTHIOPHEN 3 YL) 1 (4 (4 CHLOROPHENYL)THIAZOL 2 YL) 4,5 DIHYDRO 1H PYRAZOL 5 YL) 2 BUTYL 4 CHLORO 1H IMIDAZOLE; 5 (4 CHLOROPHENYL) 1 (4 (4 CHLOROPHENYL)THIAZOL 2 YL) 3 (2,5 DICHLOROTHIOPHEN 3 YL) 4,5 DIHYDRO 1H PYRAZOLE; 5 CHLORO 3 [ (4 CHLOROPHENYL) 1 [4 (4 CHLOROPHENYL)THIAZOL 2 YL] 4,5 DIHYDRO 1H PYRAZOL 3 YL]THIOPHENE 2 SULFONAMIDE; ADENINE; ALLOPURINOL; ANACARDIC ACID; CHLOROMETHYL AMINO PURIN; CURCUMIN; FEBUXOSTAT; FLAVONIDE; FYX 051; IMINOTHIAZOLE DERIVATIVE; N (1,3) DIARYL 3 OXOPROPYL AMIDE; N ARYL 5 AMINO 4 CYANOPYRAZOLE; NIRAXOSTAT; SCAVENGER; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; XANTHINE OXIDASE; XANTHINE OXIDASE INHIBITOR;

ANIMAL CELL; ANIMAL EXPERIMENT; ANTIOXIDANT ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTAL STRUCTURE; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME INHIBITION; ENZYME ISOLATION; MELTING POINT; MOLECULAR DOCKING; MOLECULAR MODEL; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; THIN LAYER CHROMATOGRAPHY;

ANIMALS; BIPHENYL COMPOUNDS; FREE RADICAL SCAVENGERS; GREEN CHEMISTRY TECHNOLOGY; MOLECULAR DOCKING SIMULATION; PICRATES; POLYETHYLENE GLYCOLS; RATS; RATS, WISTAR; REACTIVE OXYGEN SPECIES; SUPEROXIDES; THIOPHENES; XANTHINE OXIDASE;

EID: 84870887290     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.09.060     Document Type: Article

References (55)

1. R. Harrison Biol. Med. 21 2002 774
2. O.J. Stewart, and A. Silman J. Br. J. Rheumatol. 29 1990 485
3. P. Pacher, A. Nivorozhkin, and C. Szabo Pharmacol. Rev. 58 2006 87
4. K.T. Rott, and C.A. Agudelo J. Am. Med. Assoc. 289 2003 2857
5. K.R. Shaukath, A. Khanum, J.N. Narendra, S. Chandra, F. Ayisha, S. Balaji, G.K. Marathe, Shubha Gopal, and K.S. Rangappa Bioorg. Med. Chem. 19 2011 211
6. A.M. Youssef, E.G. Neeland, E.B. Villanueva, M.S. White, I.M. El-Ashmawy, and B. Patrick Bioorg. Med. Chem. 18 2010 5685
7. S. Al-Said, M.S. Bashandy, S.I. Al-qasoumi, and M.M. Ghorab Eur. J. Med. Chem. 46 2011 137
8. K.B. Kalpana, M. Srinivasan, and V.P. Menon Mol. Cell. Biochem. 314 2008 95
9. V. Jaishree, N. Ramdas, J. Sachin, and B. Ramesh J. Saudi Chem. Soc. 2011 10.1016/j.jscs.2011.02.007
10. Mei-Hsiu Shih, and Fang-Ying Ke Bioorg. Med. Chem. 12 2004 4633
11. D.M. Martins, B.G. Torres, P.R. Spohr, P. Machado, H.G. Bonacorso, N. Zanatta, M.A. Martins, and T. Emanuelli Basic Clin. Toxicol. X 12 2009 107
12. A.A. Bekhit, H.M.A. Ashour, Y.S.A. Ghany, A.E.A. Bekhit, and A. Baraka Eur. J. Med. Chem. 43 2008 456
13. J.L. Kane, B.H. Hirth, O. Laing, B.B. Gourlie, S. Nahill, and G. Barsomiam Bioorg. Med. Chem. Lett. 13 2003 4463
14. B.S. Dawane, S.G. Konda, G.G. Mandawad, and B.M. Shaikh Eur. J. Med. Chem. 45 2010 387
15. Lu Xiaoyun, Baojie Wan, G. Scott, and Qidong Y. Franzblau Eur. J. Med. Chem. 46 2011 3551
16. K.I. Molvi, K.K. Vasu, S.G. Yerande, V. Sudarsanam, and N. Haque Eur. J. Med. Chem. 42 2007 1049
17. F.C. Meotti, D.O. Silva, R.S. Adair, A.R.S. Dos Santos, G. Zeni, J.B.T. Rocha, and C.W. Nogueira Envi. Toxi. Pharmacol. 37 2003 37
18. K.M. Khan, Z. Nullah, M.A. Lodhi, S. Jalil, M.I. Choudhary, and A.U. Rahaman J. Enzyme Inhib. Med. Chem. 21 2006 139
19. D.G. Priest, J.B. Hynes, C.W. Jones, and W.T. Ashton J. Pharma. Sci. 63 1974 1158
20. K. Oettl, and G. Reibneggar Biochim. Biophys. Acta 1430 1999 387
21. J.F. Hsieh, S.H. Wu, Y.L. Yang, K.F. Choong, and S.T. Chen Bioorg. Med. Chem. 61 2007 3450
22. S.S. Parmar, C. Dwivedi, and A. Basheer J. Pharm. Sci. 61 1972 179
23. A.J. Peat, J.A. Boucheron, S.H. Dickerson, D. Garrido, W. Mills, J. Peckham, F. Preugschat, T. Smalley, S.L. Schweiker, J.R. Wilson, T.Y. Wang, H.Q. Zhou, and S.A. Thomson Bioorg. Med. Chem. Lett. 14 2004 2121
24. B.R. Baker, W.F. Wood, and J.A. Kozma J. Med. Chem. 11 1968 661
25. M. Chihiro, H. Nagamoto, I. Takemura, K. Kitano, H. Komatsu, K. Sekiguchi, F. Tabusa, T. Mori, M. Tominaga, and Y. Yabuuchi J. Med. Chem. 38 1995 353
26. K. Komoriya, Y. Osada, M. Hasegawa, H. Horiuchi, S. Kondo, and R.C. Couch Eur. J. Pharmacol. 250 1993 455
27. R.K. Darpan, S. Sharma, and R. Singh Expert. Opin. Ther. Patents 21 2011 1071
28. P.N. Kavitha, S. Mohan, and J. Saravanan J. Med. Chem. 1 2011 1
29. K. Nepali, A. Agarwal, S. Sapra, V. Mittal, R. Kumar, U.C. Banerjee, M.K. Gupta, N.K. Satti, O.P. Suri, and K.L. Dhar Bioorg. Med. Chem. 19 2011 5569
30. K. Nepali, G. Singh, A. Turan, A. Agarwal, S. Sapra, R. Kumar, U.C. Banerjee, P.K. Verma, N.K. Satti, M.K. Gupta, O.P. Suri, and K.L. Dhar Bioor Med. Chem. 19 2011 1950
31. T. Sato, N. Ashizawa, K. Matsumoto, T. Iwanaga, H. Nakamura, T. Inoue, and O. Nagata Bioorg. Med. Chem. Lett. 19 2009 6225
32. T. Hashimoto, A. Fukunari, I. Yamada, N. Yanaka, D. Chen, and N. Kato Biosci. Biotechnol. Biochem. 69 2005 209
33. S. Gupta, L.M. Rodrigues, A.P. Esteves, A.M.F. Oliveira-Campos, M.S.J. Nascimento, N. Nazareth, H. Cidade, M.P. Neves, E. Fernandes, M. Pinto, M.F. Nuno, S.A. Cerqueira, and N. Bras Eur. J. Med. Chem. 43 2008 771
34. L. Lespade, and S. Bercion J. Phys. Chem. B 114 2010 921
35. N. Masuoka, and I. Kubo Biochim. Biophys. Acta 168 2004 245
36. L. Shen, and J. Hong-Fang Bioorg. Med. Chem. Lett. 19 2009 5990
37. G.G. Mandawad, S.S. Chobe, O.S. Yemul, and B.S. Dawane J. Pharm. Res. 4 2011 3360
38. Beedkar, S. D.; Khobragade, C. N.; Chobe, S. S.; Dawane, B. S.; Yemul, O. S.; Int. J. Biol. Macromol., in press. http://dx.doi.org.10.1016/j.ijbiomac. 2012.02.009.
39. R.E. Orth J. Pharma. Sci. 57 1968 537
40. K.H. Lee, and J.M. Park Korean Biochem. 18 1985 214
41. O.H. Lowry, N.J. Rosebrough, A.L. Farr, and R.J. Randall J. Biol Chem. 193 1951 265
42. L.D. Kong, Y. Zhang, X. Pan, R.X. Tan, and C.H.K. Cheng Cell. Mol. Life. Sci. 57 2000 500
43. I.I. Koleva, T.A. Van-Beek, J.P.H. Linssen, A.D. Grot, and L.V. Evstatieve Phytochem. Anal. 13 2002 8
44. C.N. Khobragade, S.D. Beedkar, R. Bodhade, and A. Vinchurkar Int. J. Biol. Macromol. 48 2011 466
45. I. Muegge, and Y.A. Martin J. Med. Chem. 42 1999 791
46. I. Muegge Med. Chem. Res. 9 1999 490
47. M.J. Sippl Proteins 17 1993 355
48. B.S. Dawane, B.M. Shaikh, N.T. Khandare, V.T. Kamble, S.S. Chobe, and S.G. Konda Green. Chem. Lett. Rev. 3 2010 205
49. S.L. Jain, S. Singhal, and B. Sain Green. Chem. 9 2007 740
50. Process for the preparation of intermediates, International patent PCT/IN2010/000148, WO103550A2, 2010.
51. R.G. Bodhade, S.D. Beedkar, A.V. Manwar, and C.N. Khobragade Int J. Biol. Macromol. 47 2010 298
52. C. Congui, V. Onnis, L. Vesci, M. Castorina, and C. Pisano Bioorg. Med. Chem. 18 2010 6238
53. F. Manna, R. Fioravanti, A. Blasco, D. Secci, P. Chimenti, C. Ferlini, and G. Scambia Bioorg. Med. Chem. Lett. 15 2005 4632
54. S.K. Burley, and G.A. Petsko Science 229 1985 23
55. R.A. Laskar, S.K. Ismail, and N.A. Roy Food Chem. 122 2010 233