QSAR analysis of centrally fused 1,5-diaryl pyrazoles for cyclooxygenase inhibition using MOE-Qua-SAR descriptors

Medicinal Chemistry Research

Volumn 18, Issue 5, 2009, Pages 396-405

  Manivannan, E ^a   Chaturvedi, S C ^a  

^a DEVI AHILYA UNIVERSITY   (India)

Author keywords

COX 1; COX 2; MOE; QSAR; Selectivity

Indexed keywords

CYCLOOXYGENASE 1; CYCLOOXYGENASE 1 INHIBITOR; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITOR; PYRAZOLE DERIVATIVE;

ARTICLE; DRUG ACTIVITY; DRUG BINDING; DRUG CONFORMATION; DRUG POTENCY; DRUG SELECTIVITY; ENZYME INHIBITION; PHYSICAL CHEMISTRY; QUANTITATIVE STRUCTURE ACTIVITY RELATION; REFRACTION INDEX; REGRESSION ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 67349202203     PISSN: 10542523     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00044-008-9136-x     Document Type: Article

References (19)

1. SR Bertenshaw JJ Talley DJ Rogier MJ Graneto CM Koboldt Y Zhang 1996 Conformationally restricted 1,5-diarylpyrazoles are selective COX-2 inhibitors Bioorg Med Chem Lett 6 2827 2830 10.1016/S0960-894X(96)00530-6
2. JH Botting 1999 Nonsteroidal antiinflammatory agents Drugs Today (Barc) 35 225 235
3. G Dannhardt W Kiefer 2000 Cyclooxygenase inhibitors-current status and future prospectus Eur J Med Chem 36 109 126 10.1016/S0223-5234(01)01197-7
4. R Garg A Kurup SB Mekapati C Hansch 2003 Cycloxygenase (COX) inhibitors: a comparative QSAR study Chem Rev 103 703 731 10.1021/cr020464a
5. RG Kurumbail JY Pak D Gildehaus JM Miyashiro AM Stevens JK Gierse 1996 Structural basis for selective inhibition of cyclooxygenase-2 by antiinflammatory agents Nature 384 644 648 10.1038/384644a0
6. E Manivannan S Prasanna SC Chaturvedi 2004 Rationalization of physico-chemical properties of 5,6-diarylthiazolo [3,2-b]-1, 2,4-triazoles towards cyclooxygenase-2 (COX-2) inhibition Indian J Biochem Biophys 41 179 183
7. TD Penning JJ Talley SR Bertenshaw JS Carter PW Collins S Doctor MJ Graneto LF Lee JW Malecha JM Miyashiro RS Rojers DJ Rogier SS Yu GD Anderson EG Burton JN Cogburn SA Gregory CM Koboldt WE Perkins K Seibert AW Veenhuizen YY Zhang PC Isakson 1997 Synthesis and biological evaluation of the 1,5 diaryl pyrazole class of cyclooxygenase-2 inhibitors: identification of 4-[5-(4-methyl phenyl)-3-(triflouro methyl)-1H-pyrazol-1-yl] benzene sulfonamide (SC-58635, Celecoxib) J Med Chem 40 1347 1365 10.1021/jm960803q
8. S Prasanna E Manivannan SC Chaturvedi 2004 Quantitative structure-activity relationship analysis of a series of 2,3-diaryl benzopyran analogues as novel selective cyclooxygenase-2 inhibitors Bioorg Med Chem Lett 14 4005 4011 10.1016/j.bmcl.2004.05.059
9. S Prasanna E Manivannan SC Chaturvedi 2004 QSAR analysis of 2,3-diaryl benzopyrans/pyrans as selective COX-2 inhibitors based on semiempirical AM1 Calculations QSAR Comb Sci 23 621 628 10.1002/qsar.200430887
10. S Prasanna E Manivannan SC Chaturvedi 2004 QSAR analysis of some fused pyrazoles as cyclooxygenase inhibtors: a Hansch approach Arch Pharm Pharm Med Chem 337 440 444 10.1002/ardp.200400887
11. S Prasanna E Manivannan SC Chaturvedi 2005 QSAR studies on structurally similar 2-(4-methanesulfonylphenyl) pyran-4-ones as selective COX-2 inhibitors: a Hansch approach Bioorg Med Chem Lett 15 313 320 10.1016/j.bmcl.2004.10.077
12. S Prasanna E Manivannan SC Chaturvedi 2005 Quantitative structure-activity relationship analysis of 2,3 diaryl indoles as selective cyclooxygenase-2 inhibitors J Enzyme Inhib Med Chem 20 455 461 10.1080/14756360500277251
13. S Prasanna E Manivannan SC Chaturvedi 2005 Quantitative structure-activity relationship studies of cyclooxygenase inhibitors: a comprehensive analysis Drug Dev Res 64 220 231 10.1002/ddr.10432
14. S Prasanna E Manivannan SC Chaturvedi 2005 QSAR analyses of conformationally restricted 1,5-diarylpyrazoles as selective COX-2 inhibitors: application of connection table representation of ligands Bioorg Med Chem Lett 15 2097 2102 10.1016/j.bmcl.2005.02.035
15. P Prasit Z Wang C Brideau CC Chan S Charleson W Cromlish 1999 The discovery of rofecoxib, [MK 996, Vioxx, 4-(4'-methylsulfonylphenyl)-3-phenyl- 2(5H)-furanone], an orally active cyclooxygenase-2 inhibitor Bioorg Med Chem Lett 9 1773 1778 10.1016/S0960-894X(99)00288-7
16. JJ Talley DL Brown JS Carter MJ Granteo CM Koboldt JL Masferrer 2000 4-[5-Methyl-3-phenylisoxazol-4-yl]-benzenesulfonamide, Valdecoxib: a potent and selective inhibitor of COX-2 J Med Chem 43 775 777 10.1021/jm990577v
17. JJ Talley SR Bertenshaw DL Brown JS Carter MJ Graneto MS Kellogg 2000 N-[[(5-Methyl-3-phenyl] sulfonyl] propanamide, sodium salt, parecoxib sodium: a potent and selective inhibitor of COX-2 for parentral administration J Med Chem 43 1661 1663
18. JR Vane 1971 Inhibition of prostaglandin synthesis as a mechanism of action of Asprin-like drugs Nature 231 232 235
19. JR Vane YS Bakhle RM Botting 1998 Cyclooxygenase 1 and 2 Annu Rev Pharmacol Toxicol 38 97 120 10.1146/annurev.pharmtox.38.1.97