Synthesis of novel 2-mercaptobenzoxazole based 1,2,3-triazoles as inhibitors of proinflammatory cytokines and suppressors of COX-2 gene expression

European Journal of Medicinal Chemistry

Volumn 81, Issue , 2014, Pages 204-217

  Haider, Saqlain ^a   Alam, Mohammad Sarwar ^a   Hamid, Hinna ^a   Shafi, Syed ^a   Dhulap, Abhijeet ^c   Hussain, Firasat ^b   Alam, Perwez ^d   Umar, Sadiq ^a   Pasha, M A Q ^d   Bano, Sameena ^a   Nazreen, Syed ^a   Ali, Yakub ^a   Kharbanda, Chetna ^a  

^a HAMDARD UNIVERSITY   (India)

^b UNIVERSITY OF DELHI   (India)

^c NATIONAL CHEMICAL LABORATORY   (India)

^d CSIR INSTITUTE OF GENOMICS AND INTEGRATIVE BIOLOGY   (India)

Author keywords

Antinociceptive; Crystallography; Cyclooxygenase; Gene expression; Molecular docking

Indexed keywords

1,2,3 TRIAZOLE DERIVATIVE; 2 (1 2 TOLYL 1H[1,2,3]TRIAZOL 4 YLMETHYLSULFANYL) BENZOXAZOLE; 2 (1 PHENYL 1H [1,2,3]TRIAZOL 4 YLMETHYLSULFANYL)BENZOXAZOLE; 2 MERCAPTOBENZOXAZOLE DERIVATIVE; 2 [1 (2 BROMO PHENYL) 1H [1,2,3]TRIAZOL 4 YLMETHYLSULFANYL] BENZOXAZOLE; 2 [1 (2 CHLORO PHENYL) 1H [1,2,3]TRIAZOL 4 YLMETHYLSULFANYL] BENZOXAZOLE; 2 [1 (2 FLUORO PHENYL) 1H [1,2,3]TRIAZOL 4 YLMETHYLSULFANYL] BENZOXAZOLE; 2 [1 (3 CHLORO PHENYL) 1H [1,2,3]TRIAZOL 4 YLMETHYLSULFANYL] BENZOXAZOLE; 2 [1 (3 NITRO PHENYL) 1H [1,2,3] TRIAZOL 4 YLMETHYLSULFANYL] BENZOXAZOLE; 2 [1 (3,4 DIMETHYL PHENYL) 1H [1,2,3]TRIAZOL 4 YLMETHYLSULFANYL] BENZOXAZOLE; 2 [1 (4 BROMO PHENYL) 1H [1,2,3]TRIAZOL 4 YLMETHYLSULFANYL] BENZOXAZOLE; 2 [1 (4 CHLORO PHENYL) 1H [1,2,3]TRIAZOL 4 YLMETHYLSULFANYL] BENZOXAZOLE; 2 [1 (4 ETHOXY PHENYL) 1H [1,2,3]TRIAZOL 4 YLMETHYLSULFANYL] BENZOXAZOLE; 2 [1 (4 ETHYL PHENYL) 1H [1,2,3]TRIAZOL 4 YLMETHYLSULFANYL] BENZOXAZOLE; 2 [1 (4 FLUORO PHENYL) 1H [1,2,3]TRIAZOL 4 YLMETHYLSULFANYL] BENZOXAZOLE; 2 [1 (4 METHOXY PHENYL) 1H [1,2,3]TRIAZOL 4 YLMETHYLSULFANYL] BENZOXAZOLE; 2 [1 (4 NITRO PHENYL) 1H [1,2,3]TRIAZOL 4 YLMETHYLSULFANYL] BENZOXAZOLE; 2 [1 (4 TERT BUTYL PHENYL) 1H [1,2,3]TRIAZOL 4 YLMETHYLSULFANYL] BENZOXAZOLE; ANTIINFLAMMATORY AGENT; ANTIOXIDANT; CELECOXIB; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITOR; GLUTATHIONE; INTERLEUKIN 1BETA; NITRIC OXIDE; SUPEROXIDE DISMUTASE; THIOBARBITURIC ACID REACTIVE SUBSTANCE; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG; 2-MERCAPTOBENZOXAZOLE; ANALGESIC AGENT; BENZOXAZOLE DERIVATIVE; CYTOKINE; NONSTEROID ANTIINFLAMMATORY AGENT; THIOL DERIVATIVE; TRIAZOLE DERIVATIVE;

ANIMAL EXPERIMENT; ANTIINFLAMMATORY ACTIVITY; ANTINOCICEPTION; ANTIOXIDANT ACTIVITY; ARTICLE; DRUG METABOLISM; DRUG SYNTHESIS; FEMALE; GENE EXPRESSION; HELA CELL LINE; HUMAN; HUMAN CELL; HYDROGEN BOND; HYDROPHOBICITY; IN VIVO STUDY; LIPID PEROXIDATION; MOLECULAR DOCKING; NONHUMAN; PAW EDEMA; RAT; RHEUMATOID ARTHRITIS; STOMACH ULCER; STRUCTURE ACTIVITY RELATION; ANIMAL; ANTAGONISTS AND INHIBITORS; BIOSYNTHESIS; BLOOD; CHEMICAL STRUCTURE; CHEMICALLY INDUCED; CHEMISTRY; DRUG EFFECTS; EDEMA; GENE EXPRESSION REGULATION; GENETICS; IMMUNOLOGY; INFLAMMATION; MOUSE; PAIN; SYNTHESIS; TUMOR CELL CULTURE; WISTAR RAT;

ANALGESICS; ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; BENZOXAZOLES; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITORS; CYTOKINES; EDEMA; GENE EXPRESSION REGULATION, ENZYMOLOGIC; HELA CELLS; HUMANS; INFLAMMATION; MICE; MODELS, MOLECULAR; PAIN; RATS; RATS, WISTAR; SULFHYDRYL COMPOUNDS; TRIAZOLES; TUMOR CELLS, CULTURED;

EID: 84901060030     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.05.012     Document Type: Article

References (50)

1. M.M. Wolfe, D.R. Lichtenstein, and G. Singh N. Engl. J. Med. 340 1999 1888 1899
2. M.C. Allison, A.G. Howatson, C.J. Torrance, F.D. Lee, and R.I. Russell N. Engl. J. Med. 327 1992 749 754
3. R. Karima, S. Matsumoto, H. Higashi, and K. Matsushima Mol. Med. Today 5 1999 123 132
4. G. Schlag, H. Redl, and S. Hallstrom Resuscitation 21 1991 137 180
5. H. Birkedal-Hansen J. Periodont. Res. 28 1993 500 510
6. S. Shafi, M.M. Alam, N. Mulakayala, C. Mulakayala, G. Vanaja, A.M. Kalle, R. Pallu, and M.S. Alam Eur. J. Med. Chem. 49 2012 324 333
7. J. Susperregui, M. Bayle, J.M. Léger, and G. Déléris J. Organ. Mett. Chem. 556 1998 105 110
8. P. Kohli, S.D. Srivastava, and S.K. Srivastava J. Chin. Chem. Soc. 54 2007 1003 1010
9. V. Şunel, M. Popa, C.L. Dumitriu, A. Ciobanu, I. Bunia, and A.A. Popa React. Funct. Polym. 65 2005 367
10. S.M. Rida, F.A. Ashour, S.A.M. El-Hawash, M.M. ElSemary, M.H. Badr, and M.A. Shalaby Eur. J. Med. Chem. 40 2005 949 959
11. A.A. Hare, L. Leng, S. Gandavi, X. Du, Z. Cournia, and W.L. Jorgensen Bioorg. Med. Chem. Lett. 20 2010 5811 5814
12. J. Vinsova, K. Cermakova, A. Tomeckova, M. Ceckova, J. Jampilek, J. Kunes, M. Dolezal, and F. Staud Bioorg. Med. Chem. 14 2006 5850 5865
13. Z. Tian, D.J. Plata, S.J. Wittenberger, and A.V. Bhatia Tetrahedron. Lett. 46 2005 8341 8343
14. D.R. Buckle, and C.J.M. Rockell J. Chem. Soc. Perkin Trans. 1982 627 630
15. D.R. Buckle, D.J. Outred, C.J.M. Rockell, H. Smith, and B.A. Spicer J. Med. Chem. 26 1983 251 254
16. M.D. Chen, S.J. Lu, G.P. Yuag, S.Y. Yang, and X.L. Du Heterocyclic Comm. 6 2000 421 426
17. E.A. Sherement, R.I. Tomanov, E.V. Trukhin, and V.M. Berestovitskaya Russ. J. Org. Chem. 40 2004 594 595
18. A. Allais, and J. Meier (Roussel-UCLAF) Ger. Offen. 1969 1815467
19. K.M. Banu, A. Dinakar, and C. Ananthanarayanan Ind. J. Pharm. Sci. 4 1999 202 205
20. R. Meier EP. 199262; Eidem, US. 4789680 1986
21. A. Passannanti, P. Diana, P. Barraja, F. Mingoia, A. Lauria, and G. Cirrincione Heterocycles 48 1998 1229 1235
22. M. Jilino, and F.G. Stevens J. Chem. Soc. Perkin Trans. 1 1998 1677 1684
23. G.D. Diana, J.J. Nitz, EP. 566199, (1993).
24. H.G. Kim, E.H. Han, W.S. Jang, J.H. Choi, T. Khanal, B.H. Park, T.P. Tran, Y.C. Chung, and H.G. Jeong Food Chem. Toxicol. 50 2012 2342 2348
25. M. Duwiejua, I.J. Zeitlin, P.G. Waterman, J. Chapman, G.J. Mhango, and G.J. Provan Planta. Med. 59 1993 12 16
26. Y. Juarranz, C. Abad, C. Martinez, A. Arranz, I. Gutierrez-Canas, F. Rosignoli, R.P. Gomariz, and J. Leceta Arthritis Res. Ther. 7 2005 R1034 R1045
27. R.A. Mothana Food. Chem. Toxicol. 49 2011 2594 2599
28. G. Schett, C. Stach, J. Zwerina, R. Voll, and B. Manger Arthritis. Rheum. 58 2008 2936 2948
29. K. Bauerova, S. Ponist, D. Mihalova, F. Drafi, and V. Kuncirova Interdiscip. Toxicol. 4 2011 33 39
30. R.T. Narendhirakannan, and T.P. Limmy Immunopharmacol. Immunotoxicol. 34 2011 326 336
31. M.Q. Hassan, R.A. Hadi, Z.S. Al-Rawi, V.A. Padron, and S.J. Stohs J. Appl. Toxicol.: JAT 21 2001 69 73
32. M.M. Khan, T. Ishrat, A. Ahmad, M.N. Hoda, M.B. Khan, G. Khuwaja, P. Srivastava, S.S. Raza, F. Islam, and S. Ahmad Chem. Biol. Interact. 183 2010 255 263
33. A. Kiziltunc, S. Cogalgil, and L. Cerrahoglu Scand. J. Rheumatol. 27 1998 441 445
34. W.G. Seo, H.O. Pae, G.S. Oh, K.Y. Chai, T.O. Kwon, Y.G. Yun, N.Y. Kim, and H.T. Chung J. Ethnopharmacol. 76 2001 59 64
35. M. Shukla, K. Gupta, Z. Rasheed, K.A. Khan, and T.M. Haqqi J. Inflamm. 5 2008 9
36. S. Umar, A. Kumar, M. Sajad, J. Zargan, M.M. Ansari, S. Ahmad, C.K. Katiyar, and H.A. Khan Rheumatol. Int. 33 2013 653 657
37. Xcalibur CCD System 2007 Oxford Diffraction Ltd Abingdon, Oxfordshire, England
38. R.C. Clark, and J.S. Reid Acta. Crystallogr. A51 1995 887 897
39. CrysAlisPro (versions 1.171.34.49), Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.
40. G.M. Sheldrick Acta. Crystallogr. A64 2008 112 122
41. L.J. Farrugia J. Appl. Cryst. 45 2012 849 854
42. C.A. Winter, E.A. Risley, and G.W. Nuss Proc. Soc. Exp. Biol. Med. 111 1962 544 547
43. S.H. Ferreira J. Pharm. Pharmacol. 31 1979 648
44. U. Sadiq, H. Abu, U. Khalid, S. Mir, A. Niyaz, A. Sayeed, K.K. Chandra, and A.K. Haider Cell. Immunol. 284 2013 51 59
45. L.J. Crofford, R.L. Wilder, A.P. Ristimaki, E.F. Remmers, H.R. Epps, and T. Hla J. Clin. Invest. 93 1994 1095 1101
46. H.G. Utley, F. Bernheim, and P. Hochstein Arch. Biochem. Biophys. 118 1967 29 32
47. J. Sedlak, and R.H. Lindsay Anal. Biochem. 25 1968 192 205
48. S. Umar, J. Zargan, K. Umar, S. Ahmad, C.K. Katiyar, and H.A. Khan Chem. Biol. Interact. 197 2012 40 46
49. R. Koster, M. Anderson, and E.J. Beer Fed. Proc. 18 1959 412 416
50. S. Haider, S. Nazreen, M.M. Alam, H. Hamid, and M.S. Alam J. Ethnopharmacol. 143 2012 236 240