Synthesis of novel 2-mercapto benzothiazole and 1,2,3-triazole based bis-heterocycles: Their anti-inflammatory and anti-nociceptive activities

European Journal of Medicinal Chemistry

Volumn 49, Issue , 2012, Pages 324-333

  Shafi, Syed ^a   Mahboob Alam, Mohammad ^a   Mulakayala, Naveen ^b   Mulakayala, Chaitanya ^c   Vanaja, G ^d   Kalle, Arunasree M ^d   Pallu, Reddanna ^d   Alam, M S ^a  

^a HAMDARD UNIVERSITY   (India)

^b INSTITUTE OF LIFE SCIENCES   (India)

^c SRI KRISHNADEVARAYA UNIVERSITY   (India)

^d UNIVERSITY OF HYDERABAD   (India)

Author keywords

1,2,3 Triazole; Anti inflammatory activity; Benzothiazole; bis Heterocycles; Click chemistry; COX

Indexed keywords

2 [1 [(2,2 DIMETHYL 1,3 DIOXALAN 4YL) 1H 1,2,3 TRIAZOL 4YL]METHYLTHIO]BENZO[D]THIAZOLE; 2 [[1 (2 CHLOROPHENYL) 1H 1,2,3 TRIAZOL 4 YL]METHYLTHIO]BENZO[D]THIAZOLE; 2 [[1 (2 METHYLPHENYL) 1H 1,2,3 TRIAZOL 4 YL]METHYLTHIO]BENZO[D]THIAZOLE; 2 [[1 (3 CHLOROPHENYL) 1H 1,2,3 TRIAZOL 4 YL]METHYLTHIO]BENZO[D]THIAZOLE; 2 [[1 (3 NITROPHENYL) 1H 1,2,3 TRIAZOL 4 YL]METHYLTHIO]BENZO[D]THIAZOLE; 2 [[1 (4 BROMOPHENYL) 1H 1,2,3 TRIAZOL 4 YL]METHYLTHIO]BENZO[D]THIAZOLE; 2 [[1 (4 CHLOROPHENYL) 1H 1,2,3 TRIAZOL 4 YL]METHYLTHIO]BENZO[D]THIAZOLE; 2 [[1 (4 ETHOXYPHENYL) 1H 1,2,3 TRIAZOL 4 YL]METHYLTHIO]BENZO[D]THIAZOLE; 2 [[1 (4 FLUOROPHENYL) 1H 1,2,3 TRIAZOL 4 YL]METHYLTHIO]BENZO[D]THIAZOLE; 2 [[1 (4 NITROPHENYL) 1H 1,2,3 TRIAZOL 4 YL]METHYLTHIO]BENZO[D]THIAZOLE; 2 [[1 (PYRIDINE 3YL) 1H 1,2,3 TRIAZOL 4 YL]METHYLTHIO]BENZO[D]THIAZOLE; 2 [[1 PHENYL 1H 1,2,3 TRIAZOL 4 YL]METHYLTHIO]BENZO[D]THIAZOLE; BENZOTHIAZOLE DERIVATIVE; CARRAGEENAN; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; IBUPROFEN; UNCLASSIFIED DRUG;

ANALGESIC ACTIVITY; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CLICK CHEMISTRY; CONTROLLED STUDY; DRUG EFFICACY; DRUG POTENCY; DRUG SYNTHESIS; ENZYME ACTIVITY; FEMALE; IN VIVO STUDY; MALE; NONHUMAN; PAW EDEMA; RAT; STRUCTURE ACTIVITY RELATION; WRITHING TEST;

ANALGESICS; ANIMALS; ANTI-INFLAMMATORY AGENTS; BENZOTHIAZOLES; CLICK CHEMISTRY; CYCLOOXYGENASE INHIBITORS; EDEMA; FEMALE; HUMANS; MALE; MODELS, MOLECULAR; NOCICEPTION; RATS; RATS, WISTAR; TRIAZOLES;

EID: 84857234671     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.01.032     Document Type: Article

References (68)

1. L.L. Bozec, and C.J. Moody Aust. J. Chem. 62 2009 639
2. C.L. Lee, Y. Lam, and S. Lee Tetrahedron Lett. 42 2001 109
3. M. Bryson, B. Fulton, and P. Benfield Drugs 52 1996 549
4. M. Lacova, J. Chovancova, O. Hyblova, and S. Varkonda Chem. Pap. 45 1991 411
5. I. Chulak, V. Sutorius, and V. Sekerka Chem. Pap. 44 1990 131
6. T. Papenfuhs Ger. Offen. De. 3 1987 528
7. T.D. Bradshaw, M.C. Bibby, J.A. Double, I. Fichtner, P.A. Cooper, M.C. Alley, S. Donohue, S.F. Stinson, J.E. Tomaszewjski, E.A. Sausville, and M.F.G. Stevens Mol. Cancer Ther. 1 2002 239 246
8. T.D. Bradshaw, M.S. Chua, H.L. Browne, V. Trapani, E.A. Sausville, and M.F.G. Stevens Brit. J. Cancer 86 2002 1348 1354
9. I. Hutchinson, S.A. Jennings, B.R. Vishnu vajjala, A.D. Westwell, and M.F.G. Stevens J. Med. Chem. 45 2002 744 747
10. I. Hutchinson, M.S. Chua, H.L. Browne, V. Trapani, T.D. Bradshaw, A.D. Westwell, and M.F.G. Stevens J. Med. Chem. 44 2001 1446 1455
11. E. Kashiyama, I. Hutchinson, M.S. Chua, F. Sherman, Stinson, and R. Lawrence J. Med. Chem. 42 1999 4172 4184
12. V. Benetau, T. Besson, J. Guillard, S. Leonce, and B. Pfeiffer Eur. J. Med. Chem. 34 1999 1053 1060
13. M.A. El-Sherbeny Arzeneim-Forsch 50 2000 843 847
14. L. Racane, V. Tralic-Kulenovic, L. Fiser-Jakic, D.W. Boykin, and G. Karminski-Zamola Heterocycles 55 2001 2085 2098
15. Mahmood-ul-Hasan, Z.H. Chohan, and C.T. Supuran Main Group Met. Chem. 25 2002 291 296
16. Akhilesh Gupta, and Swati Rawat J. Curr. Pharm. Res. 3 2010 13 23
17. Sanjay K. Yadav, S.M. Malipatil, and S.K. Yadav Int. J. Drug Discov. Herbal Res. 1 2011 42 43
18. Priyanka, N.K. Sharma, and K.K. Jha Int. J. Curr. Pharm. Res. 2 2010 01 06
19. P.S. Yadav, Devprakash, and G.P. Senthilkumar Int. J. Pharm. Sci. Drug Res. 3 2011 01 07
20. P. Venkatesh, and S.N. Pandeya Int. J. Chem. Tech. Res. 1 2009 1354 1358
21. Akhilesh Gupta, and Swati Rawat J. Curr. Pharm. Res. 3 2010 13 23
22. P. Gajdoš, P. Magdolen, P. Zahradník, and P. Foltínová Molecules 14 2009 5382 5388
23. V.A. Jagtap, E. Jayachandran, G.M. Sreenivasa, and B.S. Sathe J. Pharm. Res. 4 2011 1359 1360
24. M.R. Shiradkar, K.K. Murahari, H.R. Gangadasu, T. Suresh, C.A. Kalyan, D. Panchal, R. Kaur, B. Prashant, G. Jyoti, M. Vinod, and M. Raut Bioorg. Med. Chem. Lett. 15 2007 3997 4008
25. S.P. Singh, and R.K. Vaid Indian J. Chem. 25B 1986 288
26. J. Wada, T. Suzuki, M. Iwasaki, H. Miyamatsu, S. Ueno, and M. Shimizu J. Med. Chem. 16 1973 930 934
27. E. Aki-Sener, K.K. Bingol, T. Paramashivappa, P. Phani Kumar, P.V. Subba Rao, and A. Srinivasa Rao Bioorg. Med. Chem. Lett. 13 2003 657 660
28. Y.S. Sanghvi, B.K. Bhattacharya, G.D. Kini, S.S. Matsumoto, S.B. Larson, W.B. Jolley, R.K. Robins, and G.R. Revankar J. Med. Chem. 33 1990 336 344
29. H. Wamhoff A.R. Katritzky, C.W. Rees, Comprehensive Heterocyclic Chemistry vol. 5 1984 Pergamon Oxford 669
30. M. Journet, D. Cai, J.J. Kowal, and R.D. Larsen Tetrahedron Lett. 42 2001 9117 9118
31. D.R. Buckle, and C.J.M. Rockell J. Chem. Soc. Perkin Trans. 1982 627 630
32. D.R. Buckle, D.J. Outred, C.J.M. Rockell, H. Smith, and B.A. Spicer J. Med. Chem. 26 1983 251 254
33. D.R. Buckle, C.J.M. Rockell, H. Smith, and B.A. Spicer J. Med. Chem. 29 1986 2262 2267
34. R. Alvarez, S. Velázquez, A. San Felix, S. Aquaro, E.D. Clercq, C.F. Perno, A. Karlsson, J. Balzarini, and M.J. Camarasa J. Med. Chem. 37 1994 4185 4194
35. M.J. Genin, D.A. Allwine, D.J. Anderson, M.R. Barbachyn, D.E. Emmert, S.A. Garmon, D.R. Graber, K.C. Grega, J.B. Hester, D.K. Hutchinson, J. Morris, R.J. Reischer, C.W. Ford, G.E. Zurenko, J.C. Hamel, R.D. Schaadt, D. Stapert, and B.H. Yagi J. Med. Chem. 43 2000 953 970
36. M.D. Chen, S.J. Lu, G.P. Yuag, S.Y. Yang, and X.L. Du Heterocyclic Comm. 6 2000 421 426
37. E.A. Sherement, R.I. Tomanov, E.V. Trukhin, and V.M. Berestovitskaya Russ. J. Org. Chem. 40 2004 594 595
38. A. Allais, and J. Meier (Roussel-UCLAF) Ger. Offen. 1969 1815467
39. K.M. Banu, A. Dinakar, and C. Ananthanarayanan Indian J. Pharm. Sci. 4 1999 202 205
40. R. Meier, EP. 199262; eidem, US. 4789680, 1986.
41. A. Passannanti, P. Diana, P. Barraja, F. Mingoia, A. Lauria, and G. Cirrincione Heterocycles 48 1998 1229 1235
42. M. Jilino, and F.G. Stevens J. Chem. Soc. Perkin Trans. 1 1998 1677 1684
43. G.D. Diana, J.J. Nitz, EP. 566199, 1993.
44. Y. Bourne, H.C. Kolb, Z. Radi, K.B. Sharpless, P. Taylor, and P. Marchot Proc. Natl. Acad. Sci. U.S.A. 101 2004 1449 1454
45. W.G. Lewis, L.G. Green, F. Grynszpan, Z. Radi, P.R. Carlier, P. Taylor, M.G. Finn, and K.B. Sharpless Angew. Chem. Int. Ed. 41 2002 1053 1057
46. I.A. Alsarra, M.O. Ahmed, F.K. Alanazi, K.E.H. ElTahir, M.A. Alsheikh, and H.S. Neau Int. J. Med. Sci. 7 2010 232 239
47. J.G. Ruiz, and D.T. Lowenthal Geriatr. Nephrol. Urol. 7 1997 51 57
48. H.H. Tan, W.M.C. Ong, S.H. Lai, and W.C. Chow Singapore Med. J. 48 2007 582 585
49. L.G. Howes Ther. Clin. Risk Manag. 5 2007 831 845
50. J.A. Mitchell, and T.D. Warner Nat. Rev. Drug Discov. 5 2006 75 85
51. J.J. Zhang, E.L. Ding, and Y.Q. Song JAMA 296 2006 1619 1632
52. V. Dhikav, S. Singh, and K.S. Anand J. Indian Acad. Clin. Med. 3 2002 332 338
53. H.M. Berman, J. Westbrook, Z. Feng, G. Gilliland, T.N. Bhat, H. Weissig, I.N. Shindyalov, and P.E. Bourne Protein Data Bank, Nucleic Acids Res. 28 2000 235 242
54. J.D. Thompson, D.G. Higgins, T.J. Gibson, and W. Clustal Nucleic Acids Res. 22 1994 4673 4680
55. R.A. Copeland, J.M. Williams, J. Giannaras, S. Nurnberg, M. Covington, D. Pinto, S. Pick, and J.M. Trzaskos Proc. Natl. Acad. Sci. USA. 91 23 1994 11202 11206
56. W.R. Pagels, R.J. Sachs, L.J. Marnett, D.L. Dewitt, J.S. Day, and W.L. Smith J. Biol. Chem. 258 1983 6517 6523
57. R.W. Egan, J. Paxton Jr. , and F.A. Kuehl J. Biol. Chem. 251 1976 7329 7335
58. C.A. Winter, E.A. Risley, and G.W. Nuss Proc. Soc. for Exp. Biol. Med. 111 1962 544 547
59. S.H. Ferreira J. Pharm. Pharmacol. 31 1979 648
60. S.F. Altschul, W. Gish, W. Miller, E.W. Myers, and D.J. Lipman J. Mol. Biol. 215 1990 403 410
61. S.W. Rowlinson, J.R. Keifer, J.J. Prusakiewicz, J.L. Pawlitz, K.R. Kozak, A.S. Kalgutkar, W.C. Stallings, R.G. Kurumballi, and L.J. Marnett J. Biol. Chem. 278 2003 45763 45769
62. N. Eswar, B. Webb, M.A. Marti-Renom, M.S. Madhusudhan, D. Eramian, M.Y. Shen, U. Pieper, and A. Sali Curr. Protoc. Protein Sci. 2007 (Chapter 2), Unit 29
63. K. Arnold, L. Bordoli, J. Kopp, and T. Schwede Bioinform. (Oxford, England) 22 2006 195 201
64. M. Wiederstein, and M.J. Sippl Nucleic Acids Res. 35 2007 W407 W410
65. R.A. Laskowski, M.W. MacArthur, D.S. Moss, and J.M. Thornton J. Appl. Crystallogr. 26 1993 283 291
66. K. Sumathi, P. Ananthalakshmi, M.N. Roshan, and K. Sekar Nucleic Acids Res. 34 2006 128 132
67. G.M. Morris, D.S. Goodsell, R.S. Halliday, R. Huey, W.E. Hart, R.K. Belew, and A.J. Olson J. Comput. Chem. 19 1998 1639 1662
68. R. Koster, M. Anderson, and E.J. Beer Fed. Proceeds 18 1959 412 416