Pharmacophore elucidation and molecular docking studies on 5-phenyl-1-(3-pyridyl)-1H-1,2,4-triazole-3-carboxylic acid derivatives as COX-2 inhibitors

Scientia Pharmaceutica

Volumn 78, Issue 2, 2010, Pages 195-214

  Lindner, Marc ^a   Sippl, Wolfgang ^a   Radwan, Awwad A ^b,c  

^a MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

^b Assiut University   (Egypt)

^c KING SAUD UNIVERSITY   (Saudi Arabia)

Author keywords

Catalyst; COX; Docking; GOLD; Pharmacophore

Indexed keywords

5 PHENYL 1 (3 PYRIDYL) 1H 1,2,4 TRIAZOLE 3 CARBOXYLIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CYCLOOXYGENASE 2 INHIBITOR; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIINFLAMMATORY ACTIVITY; ARTICLE; DRUG INHIBITION; DRUG MECHANISM; DRUG STRUCTURE; GEOMETRY; PHARMACOPHORE; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

EID: 77954631114     PISSN: 00368709     EISSN: 22180532     Source Type: Journal    
DOI: 10.3797/scipharm.0912-19     Document Type: Article

References (39)

1. Dogne JM, Supuran CT, Pratico D. Adverse cardiovascular effects of the coxibs. J Med Chem. 2005; 48: 2251-2257. doi:10.1021/jm0402059
2. Hinz B, Brune K. Cyclooxygenase-2-10 Years Later. J Pharmacol Exp Ther. 2002; 300: 367-375. doi:10.1124/jpet.300.2.367
3. Kurumbail RG, Stevens AM, Gierse JK, McDonald J, Stegeman RA, Pak JY, Gildehaus D, Miyashiro JM, Penning TD, Seibert K, Isakson PC, Stallings WC. Structural basis for selective inhibition of cyclooxygenase-2 by anti-inflammatory agents. Nature. 1996; 384: 644-648. doi:10.1038/384644a0
4. Wong E, Bayly C, Waterman HL, Riendeau D, Mancini JA. Conversion of prostaglandin G/H synthase-1 into an enzyme sensitive to PGHS-2-selective inhibitors by a double His513 to Arg and Ile523 to Val mutation. J Biol Chem. 1997; 272: 9280-9286. doi:10.1074/jbc.272.14.9280
5. Dannhardt G, Kiefer W. Cyclooxygenase inhibitors -current status and future prospects. Eur J Med Chem. 2001; 36: 109-126. doi:10.1016/S0223-5234(01)01197-7
6. Gauthier JY, Leblanc Y, Black WC, Chan CC, Cromlish WA, Gordon R, Kennedey BP, Lau CK, Leger S, Wang Z, Ethier D, Guay J, Mancini J, Riendeau D, Tagari P, Vickers P, Wong E, Xu L, Prasit P. Synthesis and biological evaluation of 2,3-diarylthiophenes as selective cox-2 inhibitors. part II: Replacing the heterocycle. Bioorg Med Chem Lett. 1996; 6: 87-92. doi:10.1016/0960-894X(95)00564-A
7. Zarghi A, Zebardast T, Daraie B, Hedayati M. Design and synthesis of new 1,3-benzthiazinan-4-one derivatives as selective cyclooxygenase (COX-2) inhibitors. Bioorg Med Chem. 2009; 17: 5369-5373. doi:10.1016/j.bmc.2009.06.056
8. Hashimoto H, Imamura K, Haruta J, Wakitani K. 4-(4-Cycloalkyl/aryl-oxazol-5-yl)benzenesulfonamides as Selective Cyclooxygenase-2 Inhibitors: Enhancement of the Selectivity by Introduction of a Fluorine Atom and Identification of a Potent, Highly Selective, and Orally Active COX-2 Inhibitor JTE-522. J Med Chem. 2002; 45: 1511-1517. doi:10.1021/jm010484p
9. Habeeb AG, Rao PNP, Knaus EE. Design and synthesis of 4,5-diphenyl-4-isoxazolines: novel inhibitors of cyclooxygenase-2 with analgesic and anti-inflammatory activity. J Med Chem. 2001; 44: 2921-2927. doi:10.1021/jm0101287
10. Pal M, Madan M, Padakanti S, Pattabiraman VR, Kalleda S, Vanguri A, Mullangi R, Mamidi R, Casturi SR, Malde A, Gopalakrishnan B, Yeleswarapu KR. Synthesis and cyclooxygenase-2 inhibiting property of 1,5-diarylpyrazoles with substituted benzenesulfonamide moiety as pharmacophore: preparation of sodium salt for injectable formulation. J Med Chem. 2003; 46: 3975-3984. doi:10.1021/jm020563g
11. Almansa C, Alfon J, de Arriba AF, Cavalcanti FL, Escamilla I, Gomez LA, Miralles A, Soliva R, Bartroli J, Carceller E, Merlos M, Rafanell JG. Synthesis and Structure-Activity Relationship of a New Series of COX-2 Selective Inhibitors: 1,5-Diarylimidazoles. J Med Chem. 2003; 46: 3463-3475. doi:10.1021/jm030765s
12. Dündar Y, Ünlü S, Banoǧlu E, Entrena A, Costantino G, Nunez MT, Ledo F, Şahin MF, Noyanalpan N. Synthesis and biological evaluation of 4,5-diphenyloxazolone derivatives on route towards selective COX-2 inhibitors Eur J Med Chem. 2009; 44: 1830-1837. doi:10.1016/j.ejmech.2008.10.039
13. Dannhardt G, Laufer S. Structural approaches to explain the selectivity of COX-2 inhibitors: Is there a common pharmacophore? Curr Med Chem. 2000; 7: 1101-1112. PMid:11032960
14. Song Y, Connor DT, Doubleday R, Sorenson RJ, Sercel AD, Unangst PC, Roth BD, Gilbertsen RB, Chan K, Schrier DJ, Guglietta A, Bornemeier DA, Dyer RD. Synthesis, structure activity relationship and in-vivo evaluation of substituted ditetrabutyl phenols as a novel class of potent selective and orally active cyclooxygenase-2 inhibitors, 1-thiazolone and Oxazolone series. J Med Chem. 1999; 42: 1151-1160. doi:10.1021/jm9805081
15. Palomer A, Cabre F, Pascual J, Trujillo M, Entrena A, Mauleon D, Espinosa A. Identification of novel cyclooxygenase-2 selective inhibitors using pharmacophore models. J Med Chem. 2002; 45: 1402-1411. doi:10.1021/jm010458r
16. Amyn SMR, Hassan HY, El-Koussi NA. Synthesis of 5-Phenyl-1-(3-pyridyl)-1H-1,2,4-triazole-3-carboxylic Acid Derivatives of Potential Antiinflammatory Activity. Arch Pharm. 2006; 339: 32-40. doi:10.1002/ardp.200500151
17. Catalyst, release version 4.7: Accelrys. 9685 Scranton Road. San Diego. CA 92121.
18. Barnum D, Greene J, Smellie A, Sprague P. Identification of common functional configurations among molecules. J Chem Inf Comput Sci. 1996; 36: 563-571. doi:10.1021/ci950273r
19. Li H, Sutter J, Hoffmann R. HypoGen: An automated system for generating 3D predictive pharmacophore models. In: Pharmacophore perception. Development and use in drug design. Guner OF, Ed. International University Line: La Jolla, CA, 2000: 171-189.
20. Rowlinson SW, Kiefer JR, Prusakiewicz JJ, Pawlitz JL, Kozak KR, Kalgutkar AS, Stallings WC, Kurumbail RG, Marnett LJ. A Novel Mechanism of Cyclooxygenase-2 Inhibition Involving Interactions with Ser-530 and Tyr-385. J Biol Chem. 2003; 278: 45763-45769. doi:10.1074/jbc.M305481200
21. Kiefer JR, Pawlitz JL, Moreland KT, Stegeman RA, Hood WF, Gierse JK, Stevens AM, Goodwin DC, Rowlinson SW, Marnett LJ, Stallings WC, Kurumbail RG. Structural insights into the stereochemistry of the cyclooxygenase reaction. Nature. 2000; 405: 97-101. doi:10.1038/35011103
22. Picot D, Loll P J, Garavito RM. The X-ray crystal structure of the membrane protein prostaglandin H2 synthase-1. Nature. 1994; 367: 243-249. doi:10.1038/367243a0
23. Velázquez C, Rao PNP, McDonald R, Knaus EE. Synthesis and biological evaluation of 3,4-diphenyl-1,2,5-oxadiazole-2-oxides and 3,4-diphenyl-1,2,5- oxadiazoles as potential hybrid COX-2 inhibitor/nitric oxide donor agents. Bioorg Med Chem. 2005; 13: 2749-2757. doi:10.1016/j.bmc.2005.02.034
24. Anana R, Rao PNP, Chen QH, Knaus EE. Synthesis and biological evaluation of linear phenylethynylbenzenesulfonamide regioisomers as cyclooxygenase-1/-2 (COX-1/-2) inhibitors. Bioorg Med Chem. 2006; 14: 5259-5265. doi:10.1016/j.bmc.2006.03.050
25. Malkowski MG, Thuresson ED, Lakkides KM, Rieke CJ, Micielli R, Smith WL, Garavito RM. Structure of eicosapentaenoic and linoleic acids in the cyclooxygenase site of prostaglandin endoperoxide H synthase-1. J Biol Chem. 2001; 276: 37547-37555. doi:10.1074/jbc.M105982200
26. Malkowski MG, Ginell SL, Smith WL, Garavito RM. The productive conformation of arachidonic acid bound to prostaglandin synthase. Science. 2000; 289: 1933-1937. doi:10.1126/science.289.5486.1933
27. Gupta K, Selinsky BS, Kaub CJ, Katz AK, Loll PJ. The 2.0Ǎ Resolution Crystal Structure of Prostaglandin H(2) Synthase-1: Structural Insights into an Unusual Peroxidase. J Mol Biol. 2004; 335: 503-518. doi:10.1016/j.jmb.2003.10.073
28. Loll PJ, Picot D, Ekabo O, Garavito RM. Synthesis and use of iodinated nonsteroidal antiinflammatory drug analogs as crystallographic probes of the prostaglandin H2 synthase cyclooxygenase active site. Biochemistry. 1996; 35: 7330-7340.
29. Thuresson ED, Malkowski MG, Lakkides KM, Rieke CJ, Mulichak AM, Ginell SL, Garavito RM, Smith WL. Mutational and X-ray crystallographic analysis of the interaction of dihomo-gamma-linolenic acid with prostaglandin endoperoxide H synthases. J Biol Chem. 2001; 276: 10358-10365. doi:10.1074/jbc.M009378200
30. Selinsky BS, Gupta K, Sharkey CT, Loll P. Structural analysis of NSAID binding by prostaglandin H2 synthase: time-dependent and timeindependent inhibitors elicit identical enzyme conformations. Biochemistry. 2001; 40: 5172-5180. doi:10.1021/bi010045s
31. Wang R, Lai L, Wang S. Further development and validation of empirical scoring functions for structure-based binding affinity prediction. J Comput-Aided Mol Des. 2002; 16: 11-26. doi:10.1023/A:1016357811882
32. Smellie A., Teig S L, Towbin P. Poling: Promoting Conformational Coverage. J Comput Chem 1995; 16: 171-187. doi:10.1002/jcc.540160205
33. Sprague PW. Automated Chemical Hypothesis Generation and Database Searching with Catalyst. In: Perspectives in Drug Discovery and Design. Müller K, Ed. ESCOM Science Publishers B. V.: Leiden. The Netherlands, 1995: Vol. 3, 1-20.
34. Greene J., Kahn S., Savoj H., Sprague P, Teig S. Chemical Function Queries for 3D Database Search. J Chem Inf. Comput. Sci. 1994; 34: 1297-1308. doi:10.1021/ci00022a012
35. Clement OO, Trope-Mehl A. HipHop: Pharmacophores based on multiple common-feature alignments. In Pharmacophore Perception. Development. And Use in Drug Design. Güner OF, Ed. International University Line: La Jolla, CA, 2000: 69-83.
36. Sybyl 7.1 2005; Tripos Inc., St.Louis, USA.
37. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE. The Protein Data Bank. Nucleic Acids Research. 2000;28: 235-242. doi:10.1093/nar/28.1.235
38. Jones G, Willet P, Glen RC, Leach AR, Taylor R. Development and validation of a genetic algorithm for flexible docking. J Mol Biol. 1997; 267: 727-748. doi:10.1006/jmbi.1996.0897
39. Molecular Operating Environment 2005.06, Chemical Computing Group Inc., Montreal, Canada.