메뉴 건너뛰기




Volumn 27, Issue 2, 2012, Pages 249-260

QSAR of 2-(4-methylsulphonylphenyl)pyrimidine derivatives as cyclooxygenase-2 inhibitors: Simple structural fragments as potential modulators of activity

Author keywords

2 (4 Methylsulphonylphenyl)pyrimidines; Combinatorial protocol in multiple linear regression (CP MLR); COX 2 inhibitory activity; Dragon descriptors; Partial least square (PLS) analysis

Indexed keywords

2(4 METHYLSULPHONYLPHENYL) PYRIMIDINE DERIVATIVE; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITOR; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 84858139210     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756366.2011.587414     Document Type: Article
Times cited : (8)

References (53)
  • 1
    • 0025005862 scopus 로고
    • Te induction and suppression of prostaglandin H2 synthase (cyclooxygenase) in human monocytes
    • Fu JY, Masferrer JL, Seibert K, Raz A, Needleman P. Te induction and suppression of prostaglandin H2 synthase (cyclooxygenase) in human monocytes. J Biol Chem 1990;265:16737-16740.
    • (1990) J Biol Chem , vol.265 , pp. 16737-16740
    • Fu, J.Y.1    Masferrer, J.L.2    Seibert, K.3    Raz, A.4    Needleman, P.5
  • 4
    • 0025871150 scopus 로고
    • TIS10, a phorbol ester tumor promoter-inducible mRNA from Swiss 3T3 cells, encodes a novel prostaglandin synthase/cyclooxygenase homologue
    • Kujubu DA, Fletcher BS, Varnum BC, Lim RW, Herschman HR. TIS10, a phorbol ester tumor promoter-inducible mRNA from Swiss 3T3 cells, encodes a novel prostaglandin synthase/cyclooxygenase homologue. J Biol Chem 1991;266:12866-12872.
    • (1991) J Biol Chem , vol.266 , pp. 12866-12872
    • Kujubu, D.A.1    Fletcher, B.S.2    Varnum, B.C.3    Lim, R.W.4    Herschman, H.R.5
  • 5
    • 0028044609 scopus 로고
    • Towards a better aspirin
    • DOI 10.1038/367215a0
    • Vane J. Towards a better aspirin. Nature 1994;367:215-216. (Pubitemid 24051134)
    • (1994) Nature , vol.367 , Issue.6460 , pp. 215-216
    • Vane, J.1
  • 8
    • 0032701224 scopus 로고    scopus 로고
    • The cyclooxygenase isoforms: Structural insights into the conversion of arachidonic acid to prostaglandins
    • DOI 10.1016/S1388-1981(99)00147-X, PII S138819819900147X
    • Garavito RM, DeWitt DL. Te cyclooxygenase isoforms: structural insights into the conversion of arachidonic acid to prostaglandins. Biochim Biophys Acta 1999;1441:278-287. (Pubitemid 29537747)
    • (1999) Biochimica et Biophysica Acta - Molecular and Cell Biology of Lipids , vol.1441 , Issue.2-3 , pp. 278-287
    • Garavito, R.M.1    Dewitt, D.L.2
  • 9
    • 0033526928 scopus 로고    scopus 로고
    • Te discovery of rofecoxib [MK 966, Vioxx, 4-(4′- methylsulfonylphenyl)-3-phenyl-2(5H)-furanone] an orally active cyclooxygenase-2-inhibitor
    • Prasit P, Wang Z, Brideau C, Chan CC, Charleson S, Cromlish W et al. Te discovery of rofecoxib [MK 966, Vioxx, 4-(4′-methylsulfonylphenyl)-3- phenyl-2(5H)-furanone], an orally active cyclooxygenase-2-inhibitor. Bioorg Med Chem Lett 1999;9:1773-1778.
    • (1999) Bioorg Med Chem Lett , vol.9 , pp. 1773-1778
    • Prasit, P.1    Wang, Z.2    Brideau, C.3    Chan, C.C.4    Charleson, S.5    Cromlish, W.6
  • 10
    • 84858146591 scopus 로고    scopus 로고
    • Merck & Co. Press Release; 30 September 2004.
    • Merck & Co. Press Release; 30 September 2004. http://www.merck. com
  • 12
    • 2542570187 scopus 로고    scopus 로고
    • Cyclo-oxygenase-2 inhibitors versus non-selective non-steroidal anti-inflammatory drugs and congestive heart failure outcomes in elderly patients: A population-based cohort study
    • DOI 10.1016/S0140-6736(04)16299-5, PII S0140673604162995
    • Mamdani M, Juurlink DN, Lee DS, Rochon PA, Kopp A, Naglie G et al. Cyclo-oxygenase-2 inhibitors versus non-selective non-steroidal anti-infammatory drugs and congestive heart failure outcomes in elderly patients: a population-based cohort study. Lancet 2004;363:1751-1756. (Pubitemid 38698377)
    • (2004) Lancet , vol.363 , Issue.9423 , pp. 1751-1756
    • Mamdani, M.1    Juurlink, D.N.2    Lee, D.S.3    Rochon, P.A.4    Kopp, A.5    Naglie, G.6    Austin, P.C.7    Laupacis, A.8    Stukel, T.A.9
  • 13
    • 9644289351 scopus 로고    scopus 로고
    • Retrait du rofecoxib (Vioxx®): A propos de la sécurité cardiovasculaire des anti-inflammatoires non stéroïdiens COX-2 sélectifs
    • Scheen AJ. [Withdrawal of rofecoxib (Vioxx): what about cardiovascular safety of COX-2 selective non-steroidal anti-infammatory drugs?]. Rev Med Liege 2004;59:565-569. (Pubitemid 39573114)
    • (2004) Revue Medicale de Liege , vol.59 , Issue.10 , pp. 565-569
    • Scheen, A.J.1
  • 16
    • 6044274282 scopus 로고    scopus 로고
    • Coxibs and cardiovascular disease
    • Fitzgerald GA. Coxibs and cardiovascular disease. N Engl J Med 2004;351:1709-1711.
    • (2004) N Engl J Med , vol.351 , pp. 1709-1711
    • Fitzgerald, G.A.1
  • 17
    • 33745929924 scopus 로고    scopus 로고
    • Time-to-event analyses for long-term treatments - The APPROVe trial
    • DOI 10.1056/NEJMp068137
    • Lagakos SW. Time-to-event analyses for long-term treatments-the APPROVe trial. N Engl J Med 2006;355:113-117. (Pubitemid 44050391)
    • (2006) New England Journal of Medicine , vol.355 , Issue.2 , pp. 113-117
    • Lagakos, S.W.1
  • 20
    • 0036401149 scopus 로고    scopus 로고
    • Valdecoxib
    • Ormrod D, Wellington K, Wagstaf AJ. Valdecoxib. Drugs 2002;62:2059-2071; discussion 2072. (Pubitemid 35204038)
    • (2002) Drugs , vol.62 , Issue.14 , pp. 2059-2071
    • Ormrod, D.1    Wellington, K.2    Wagstaff, A.J.3
  • 24
    • 5144221835 scopus 로고    scopus 로고
    • Lessons from the withdrawal of rofecoxib: Patients would be safer if drug companies disclosed adverse events before licensing
    • Paul AD, Shah E, Richard MM, Peter J. Lessons from the withdrawal of rofecoxib: patients would be safer if drug companies disclosed adverse events before licensing. Br Med J 2004;329:867-868.
    • (2004) Br Med J , vol.329 , pp. 867-868
    • Paul, A.D.1    Shah, E.2    Richard, M.M.3    Peter, J.4
  • 25
    • 0242690224 scopus 로고    scopus 로고
    • COX-2 and beyond: Approaches to prostaglandin inhibition in human disease
    • FitzGerald GA. COX-2 and beyond: approaches to prostaglandin inhibition in human disease. Nat Rev Drug Discov 2003;2:879-890.
    • (2003) Nat Rev Drug Discov , vol.2 , pp. 879-890
    • Fitzgerald, G.A.1
  • 26
    • 16244365087 scopus 로고    scopus 로고
    • COX-2 selective inhibitors cardiac toxicity: Getting to the heart of the matter
    • Davies NM, Jamali F. COX-2 selective inhibitors cardiac toxicity: getting to the heart of the matter. J Pharm Pharm Sci 2004;7:332-336. (Pubitemid 41528882)
    • (2004) Journal of Pharmacy and Pharmaceutical Sciences , vol.7 , Issue.3 , pp. 332-336
    • Davies, N.M.1    Jamali, F.2
  • 27
  • 28
    • 17144393290 scopus 로고    scopus 로고
    • Adverse cardiovascular efects of the coxibs
    • Dogné JM, Supuran CT, Pratico D. Adverse cardiovascular efects of the coxibs. J Med Chem 2005;48:2251-2257.
    • (2005) J Med Chem , vol.48 , pp. 2251-2257
    • Dogné, J.M.1    Supuran, C.T.2    Pratico, D.3
  • 29
    • 33646010355 scopus 로고    scopus 로고
    • Coxibs and cardiovascular side-efects: From light to shadow
    • Dogné JM, Hanson J, Supuran C, Pratico D. Coxibs and cardiovascular side-efects: from light to shadow. Curr Pharm Des 2006;12:971-975.
    • (2006) Curr Pharm des , vol.12 , pp. 971-975
    • Dogné, J.M.1    Hanson, J.2    Supuran, C.3    Pratico, D.4
  • 30
    • 31044441042 scopus 로고    scopus 로고
    • Biological basis for the cardiovascular consequences of COX-2 inhibition: Therapeutic challenges and opportunities
    • DOI 10.1172/JCI27291
    • Grosser T, Fries S, FitzGerald GA. Biological basis for the cardiovascular consequences of COX-2 inhibition: therapeutic challenges and opportunities. J Clin Invest 2006;116:4-15. (Pubitemid 43121782)
    • (2006) Journal of Clinical Investigation , vol.116 , Issue.1 , pp. 4-15
    • Grosser, T.1    Fries, S.2    FitzGerald, G.A.3
  • 31
    • 33749440081 scopus 로고    scopus 로고
    • Cyclooxygenase inhibition and atherothrombosis
    • DOI 10.2174/138945006778559102
    • Sohn HY, Krötz F. Cyclooxygenase inhibition and atherothrombosis. Curr Drug Targets 2006;7:1275-1284. (Pubitemid 44509690)
    • (2006) Current Drug Targets , vol.7 , Issue.10 , pp. 1275-1284
    • Sohn, H.-Y.1    Krotz, F.2
  • 32
    • 30344461256 scopus 로고    scopus 로고
    • Comparative cardiovascular safety of traditional nonsteroidal anti-inflammatory drugs
    • DOI 10.1517/14740338.5.1.83
    • Maillard M, Burnier M. Comparative cardiovascular safety of traditional nonsteroidal anti-infammatory drugs. Expert Opin Drug Saf 2006;5:83-94. (Pubitemid 43056441)
    • (2006) Expert Opinion on Drug Safety , vol.5 , Issue.1 , pp. 83-94
    • Maillard, M.1    Burnier, M.2
  • 33
    • 33645741614 scopus 로고    scopus 로고
    • Coxibs, non-steroidal anti-infammatory drugs and cardiovascular risk
    • Hermann M, Ruschitzka F. Coxibs, non-steroidal anti-infammatory drugs and cardiovascular risk. Intern Med J 2006;36:308-319.
    • (2006) Intern Med J , vol.36 , pp. 308-319
    • Hermann, M.1    Ruschitzka, F.2
  • 34
    • 40749135792 scopus 로고    scopus 로고
    • Novel 2-(4-methylsulfonylphenyl)pyrimidine derivatives as highly potent and specific COX-2 inhibitors
    • DOI 10.1016/j.bmc.2007.11.079, PII S0968089607010474
    • Orjales A, Mosquera R, López B, Olivera R, Labeaga L, Núñez MT. Novel 2-(4-methylsulfonylphenyl)pyrimidine derivatives as highly potent and specifc COX-2 inhibitors. Bioorg Med Chem 2008;16:2183-2199. (Pubitemid 351380955)
    • (2008) Bioorganic and Medicinal Chemistry , vol.16 , Issue.5 , pp. 2183-2199
    • Orjales, A.1    Mosquera, R.2    Lopez, B.3    Olivera, R.4    Labeaga, L.5    Nunez, M.T.6
  • 35
    • 78650177876 scopus 로고    scopus 로고
    • Pharmacophore generation and atom-based 3D-QSAR of novel 2-(4-methylsulfonylphenyl)pyrimidines as COX-2 inhibitors
    • Shah UA, Deokar HS, Kadam SS, Kulkarni VM. Pharmacophore generation and atom-based 3D-QSAR of novel 2-(4-methylsulfonylphenyl)pyrimidines as COX-2 inhibitors. Mol Divers 2010;14:559-568.
    • (2010) Mol Divers , vol.14 , pp. 559-568
    • Shah, U.A.1    Deokar, H.S.2    Kadam, S.S.3    Kulkarni, V.M.4
  • 36
    • 84861913917 scopus 로고    scopus 로고
    • Hansch analysis of novel pyrimidine derivatives as highly potent and specifc COX-2 inhibitors
    • DOI: 10.1007/s00044-011-9566-8
    • Khare A, Trivedi S, Rajak H, Pawar RS, Patil UK, Singour PK. Hansch analysis of novel pyrimidine derivatives as highly potent and specifc COX-2 inhibitors. Med Chem Res. DOI: 10.1007/s00044-011-9566-8.
    • Med Chem Res
    • Khare, A.1    Trivedi, S.2    Rajak, H.3    Pawar, R.S.4    Patil, U.K.5    Singour, P.K.6
  • 38
    • 84858146592 scopus 로고    scopus 로고
    • Chemdraw Ultra 6.0 and Chem3D Ultra, Cambridge Soft Corporation, Cambridge, USA
    • Chemdraw Ultra 6.0 and Chem3D Ultra, Cambridge Soft Corporation, Cambridge, USA.
  • 39
    • 0042970262 scopus 로고    scopus 로고
    • A combinatorial approach to the variable selection in multiple linear regression: Analysis of Selwood et al. data set - A case study
    • Prabhakar YS. A combinatorial approach to the variable selection in multiple linear regression: analysis of Selwood et al. Data Set-a case study. QSAR Comb Sci 2003;22:583-595. (Pubitemid 37010625)
    • (2003) QSAR and Combinatorial Science , vol.22 , Issue.6 , pp. 583-595
    • Prabhakar, Y.S.1
  • 40
    • 84951601886 scopus 로고
    • Cross-validatory estimation of the number of components in factor and principal components models
    • Wold S. Cross-validatory estimation of the number of components in factor and principal components models. Technometrics 1978;20:397-405.
    • (1978) Technometrics , vol.20 , pp. 397-405
    • Wold, S.1
  • 42
    • 8544221331 scopus 로고    scopus 로고
    • Multivariate data analysis and experimental design
    • Ellis GP, West WB, eds Elsevier Science Publishers, BV
    • Stahle L, Wold S. Multivariate data analysis and experimental design, In: Ellis GP, West WB, eds. Biomedical Research, Progress in Medicinal Chemistry. Elsevier Science Publishers, BV,vol. 25, 1998, pp. 291-338.
    • (1998) Biomedical Research, Progress in Medicinal Chemistry , vol.25 , pp. 291-338
    • Stahle, L.1    Wold, S.2
  • 43
    • 0031434910 scopus 로고    scopus 로고
    • Three-dimensional quantitative structure-activity relationships from molecular similarity matrices and genetic neural networks. 1. Method and validations
    • DOI 10.1021/jm970487v
    • So SS, Karplus M. Tree-dimensional quantitative structure-activity relationships from molecular similarity matrices and genetic neural networks. 1. Method and validations. J Med Chem 1997;40:4347-4359. (Pubitemid 28042314)
    • (1997) Journal of Medicinal Chemistry , vol.40 , Issue.26 , pp. 4347-4359
    • So, S.-S.1    Karplus, M.2
  • 44
    • 8544239371 scopus 로고    scopus 로고
    • CP-MLR/PLS directed structure-activity modeling of the HIV-1 RT inhibitory activity of 2,3-diaryl-1,3-thiazolidin-4-ones
    • DOI 10.1002/qsar.200330854
    • Prabhakar YS, Solomon VR, Rawal RK, Gupta MK, Katti SB. CP-MLR/PLS directed structure-activity modeling of the HIV-1 RT inhibitory activity of 2,3-diaryl-1,3-thiazolidin-4-ones. QSAR Comb Sci 2004;23:234-244. (Pubitemid 39490415)
    • (2004) QSAR and Combinatorial Science , vol.23 , Issue.4 , pp. 234-244
    • Prabhakar, Y.S.1    Solomon, V.R.2    Rawal, R.K.3    Gupta, M.K.4    Katti, S.B.5
  • 45
    • 34250628103 scopus 로고    scopus 로고
    • Principles of QSAR models validation: Internal and external
    • DOI 10.1002/qsar.200610151
    • Gramatica P. Principles of QSAR models validation: internal and external. QSAR Comb Sci 2007;26:694-701. (Pubitemid 46932857)
    • (2007) QSAR and Combinatorial Science , vol.26 , Issue.5 , pp. 694-701
    • Gramatica, P.1
  • 48
    • 0013504617 scopus 로고
    • Applied Statistics
    • Springer-Verlag Berlin
    • Sachs L. Applied Statistics. A Handbook of Techniques. Springer-Verlag, Berlin, 1982.
    • (1982) A Handbook of Techniques
    • Sachs, L.1
  • 49
    • 41949116226 scopus 로고    scopus 로고
    • On some aspects of variable selection for partial least squares regression models
    • Roy PP, Roy K. On some aspects of variable selection for partial least squares regression models. QSAR Comb Sci 2008;27:302-313.
    • (2008) QSAR Comb Sci , vol.27 , pp. 302-313
    • Roy, P.P.1    Roy, K.2
  • 50
    • 67249129284 scopus 로고    scopus 로고
    • On two novel parameters for validation of predictive QSAR models
    • Pratim Roy P, Paul S, Mitra I, Roy K. On two novel parameters for validation of predictive QSAR models. Molecules 2009;14:1660-1701.
    • (2009) Molecules , vol.14 , pp. 1660-1701
    • Pratim Roy, P.1    Paul, S.2    Mitra, I.3    Roy, K.4
  • 51
    • 78649543896 scopus 로고    scopus 로고
    • Exploring quantitative structure-activity relationship studies of antioxidant phenolic compounds obtained from traditional Chinese medicinal plants
    • Mitra I, Saha A, Roy K. Exploring quantitative structure-activity relationship studies of antioxidant phenolic compounds obtained from traditional Chinese medicinal plants. Mol Simulat 2010;36:1067-1079.
    • (2010) Mol Simulat , vol.36 , pp. 1067-1079
    • Mitra, I.1    Saha, A.2    Roy, K.3
  • 53
    • 33244488303 scopus 로고    scopus 로고
    • Topological descriptors in modeling the antimalarial activity of 4-(3′,5′-disubstituted anilino)quinolines
    • DOI 10.1021/ci0501140
    • Gupta MK, Prabhakar YS. Topological descriptors in modeling the antimalarial activity of 4-(3′,5′-disubstituted anilino)quinolines. J Chem Inf Model 2006;46:93-102. (Pubitemid 43282103)
    • (2006) Journal of Chemical Information and Modeling , vol.46 , Issue.1 , pp. 93-102
    • Gupta, M.K.1    Prabhakar, Y.S.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.