2-(2-Arylphenyl)benzoxazole as a novel anti-inflammatory scaffold: Synthesis and biological evaluation

ACS Medicinal Chemistry Letters

Volumn 5, Issue 5, 2014, Pages 512-516

  Seth, Kapileswar ^a   Garg, Sanjeev K ^a   Kumar, Raj ^a   Purohit, Priyank ^a   Meena, Vachan S ^a   Goyal, Rohit ^b,c   Banerjee, Uttam C ^a   Chakraborti, Asit K ^a  

^a NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

^b ISF COLLEGE OF PHARMACY   (India)

^c SHOOLINI UNIVERSITY   (India)

Author keywords

2 (2 Arylphenyl)benzoxazoles; 3D QSAR; cyclooxygenase 2 selective; in vivo potency; novel anti inflammatory scaffold

Indexed keywords

2 (2 ARYLPHENYL)BENZOXAZOLE; BENZOXAZOLE DERIVATIVE; CARRAGEENAN; CELECOXIB; CYCLOOXYGENASE 1 INHIBITOR; CYCLOOXYGENASE 2 INHIBITOR; DICLOFENAC; ETORICOXIB; NONSTEROID ANTIINFLAMMATORY AGENT; ROFECOXIB; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG POTENCY; DRUG SYNTHESIS; ENZYME INHIBITION; IC 50; IN VITRO STUDY; IN VIVO STUDY; NONHUMAN; PAW EDEMA; PHARMACOPHORE; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RAT; SUZUKI REACTION;

EID: 84900428530     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml400500e     Document Type: Article

References (31)

1. Simmons, D. L. What makes a good anti-inflammatory drug target? Drug Discovery Today 2006, 11, 210-219
2. Navarro-González, J. F.; Mora-Fernández, C.; de Fuentas, M. M.; García-Pérez, J. Inflammatory molecules and pathways in the pathogenesis of diabetic nephropathy Nat. Rev. Nephrol. 2011, 7, 327-340
3. Mantovani, A.; Allavena, P.; Sica, A.; Balkwill, F. Cancer-related inflammation Nature 2008, 454, 436-444
4. Melnikova, I. Pain market Nat. Rev. Drug Discovery 2010, 9, 589-590
5. Naz, S. M.; Symmons, D. P. M. Mortality in established rheumatoid arthritis Best. Pract. Res. Clin. Rheumatol. 2007, 21, 871-883
6. Gabriel, S. E. Why do people with rheumatoid arthritis still die prematurely? Ann. Rheum. Dis. 2008, 67 (Suppl. 3) iii30-iii34
7. Summers, G. D.; Metsios, G. S.; Stavropoulos-Kalinoglou, A.; Kitas, G. D. Rheumatoid cachexia and cardiovascular disease Nat. Rev. Rheumatol. 2010, 6, 445-451
8. Marnett, L. J.; Rowlinson, S. W.; Goodwin, D. C.; Kalgutkar, A. S.; Lanzo, C. A. Arachidonic acid oxygenation by COX-1 and COX-2 J. Biol. Chem. 1999, 274, 22903-22906
9. Masferrer, J. L.; Zweifel, B. S.; Manning, P. T.; Hauser, S. D.; Leahy, K. M.; Smith, W. G.; Isakson, P. C.; Seibert, K. Selevtive inhibition of inducible cyclooxygenase 2 in vivo is anti-inflammatory and nonulcerogenic Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 3228-3232
10. Dogné, J. M.; Supuran, C. T.; Pratico, D. Adverse cardiovascular effects of the coxibs J. Med. Chem. 2005, 48, 2251-2257
11. Cannon, C. P.; Cannon, P. J. COX-2 inhibitors and cardiovascular risk Science 2012, 336, 1386-1387
12. Shono, T.; Tofilon, P. J.; Bruner, J. M.; Owolabi, O.; Lang, F. F. Cyclooxygenase-2 expression in human gliomas: prognostic significance and molecular correlations Cancer. Res. 2001, 61, 4375-4381
13. Karim, A.; Mccarthy, K.; Jawahar, A.; Smith, D.; Willis, B.; Nanda, A. Differential cyclooxygenas-2 enzyme expression in radiosensitive versus redioresistant glioblastoma multiforme cell lines Anticancer Res. 2005, 25, 675-679
14. Bijnsdorp, I. V.; van den Berg, J.; Kuipers, G. K.; Wedekind, L. E.; Slotman, B. J.; van Rijn, J.; Lafleur, M. V. M.; Sminia, P. Radiosensitizing potential of the selective cyclooxygenase-2 (COX-2) inhibitor meloxicam on human glioma cells J. Neurooncol. 2007, 85, 25-31
15. Kang, K. B.; Wang, T. T.; Woon, C. T.; Cheah, E. S.; Moore, X. L.; Zhu, C.; Wong, M. C. Enhancement of glioblastoma radioresponse by a selective COX-2 inhibitor celecoxib: inhibition of tumor angeiogenesis with extensive tumor necrosis Int. Radiat. Oncol. Biol. Phys. 2007, 67, 888-896
16. Höcherl, K.; Schmidt, C.; Bucher, M. COX-2 inhibition attenuates endotoxin-induced downregulation of organic anion transporters in the rat renal cortex Kidney Int. 2009, 75, 373-380
17. Schneider, F.; Meziani, F.; Chartier, C.; Alt, M.; Jaeger, A. Fatal allergic vasculitis associated with celecoxib Lancet 2002, 359, 852-853
18. Woodcock, J. A difficult balance: pain management, drug safety, and the FDA N. Engl. J. Med. 2009, 361, 2105-2107
19. Dannenberg, A. J.; Altorki, N. K.; Boyle, J. O.; Dang, C.; Howe, L. R.; Weksler, B. B.; Subbaramaiah, K. Cyclooxogenase 2: a pharmacological target for prevention of cancer Lancet Oncol. 2001, 2, 544-551
20. Thun, M. J.; Henley, S. J.; Patrono, C. Nonsteroidal anti-inflammatory drugs as anticancer agents: mechanistic, pharmacologic, and clinical issues J. Natl. Cancer. Ist. 2002, 94, 252-266
21. Arber, N.; DuBois, R. N. Nonsteroidal anti-inflammatory drugs and prevention of colorectal cancer Curr. Gastroenterol. Rep. 1999, 1, 441-448
22. Gupta, R. A.; DuBois, R. N. Colorectal cancer prevention and treatment by inhibition of cyclooxygenase-2 Nat. Rev. Cancer. 2001, 1, 11-21
23. Chakraborti, A. K.; Garg, S. K.; Kumar, R.; Motiwala, H. F.; Jadhavar, P. S. Progress in COX-2 inhibitors: a jounney so far Curr. Med. Chem. 2010, 17, 1563-1593
24. Rigas, B.; Kashfi, K. Cancer prevention: a new era beyond cyclooxygenase-2 J. Pharmacol. Exp. Ther. 2005, 314, 1-8
25. Grösch, S.; Maier, T. J.; Schiffmann, S.; Geisslinger, G. Cyclooxygenase-2 (COX-2)-independent anticarcinogenic effects of selective COX-2 inhibitors J. Nat. Cancer. Inst. 2006, 98, 736-747
26. Kaur, J.; Vaish, V.; Sanyal, S. N. COX-2 as a molecular target of colon cancer chemoprevention: promise and reality Biomed. Aging Pathol. 2012, 2, 67-72
27. Sun, H.; Tawa, G.; Wallqvist, A. Classification of scaffold-hopping approaches Drug Discovery Today 2012, 17, 310-324
28. Blobaum, A. L.; Marnett, L. J. Structural and functional basis of cyclooxygenase inhibition J. Med. Chem. 2007, 50, 1425-1441
29. Kumar, D.; Rudrawar, S.; Chakraborti, A. K. One-pot synthesis of 2-substituted benzoxazoles directly from carboxylic acids Aust. J. Chem. 2008, 61, 881-887
30. Kumar, R.; Selvam, C.; Kaur, G.; Chakraborti, A. K. Microwave-assisted direct synthesis of 2-substituted benzoxazoles from carboxylic acids under catalyst and solvent free conditions Synlett 2005, 1401-1404
31. Winter, C. A.; Risley, E. A.; Nuss, G. W. Anti-inflammatory and antipyretic activities of indomethacin, 1-(p -chlorobenzoyl)-5-methoxy-2- methylindole-3-acetic acid J. Pharmacol. Exp. Ther. 1963, 141, 369-376