메뉴 건너뛰기




Volumn 5, Issue 5, 2009, Pages 440-445

QSAR investigations on benzylideneamino and phenyliminomethyl scaffolds for selective COX-2 inhibition: A Hansch approach

Author keywords

4 benzylideneamino; 4 phenyliminomethyl; Aryl sulfonamide; COX 1; COX 2; NSAIDs; QSAR; Selectivity

Indexed keywords

CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; SULFONAMIDE;

EID: 70349122563     PISSN: 15734064     EISSN: None     Source Type: Journal    
DOI: 10.2174/157340609789117877     Document Type: Article
Times cited : (4)

References (20)
  • 1
    • 0032807819 scopus 로고    scopus 로고
    • Nonsteroidal antiinflammatory agents
    • Botting, J. H. Nonsteroidal antiinflammatory agents. Drugs Today, 1999, 35, 225-235.
    • (1999) Drugs Today , vol.35 , pp. 225-235
    • Botting, J.H.1
  • 2
    • 0015237292 scopus 로고
    • Inhibition of prostaglandin synthesis as a mechanism of action of Asprin-like drugs
    • Vane, J. R. Inhibition of prostaglandin synthesis as a mechanism of action of Asprin-like drugs. Nature (London), 1971, 231, 232-235.
    • (1971) Nature (London) , vol.231 , pp. 232-235
    • Vane, J.R.1
  • 4
    • 13444266910 scopus 로고    scopus 로고
    • Penning, T. D.; Talley, J. J.; Bertenshaw, S. R.; Carter, J. S.; Collins, P. W.; Doctor, S.; Graneto, M. J.; Lee, L. F.; Malecha, J. W.; Miyashiro, J. M.; Rogers, R. S.; Rogier, D. J.; Yu, S. S.; Anderson, G. D.; Burton, E. G.; Cogburn, J. N.; Gregory, S. A.; Koboldt, C. M.; Perkins, W. E.; Seibert, K.; Veenhuizen, A. W.; Zhang, Y. Y.; Isakson, P. C. 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., 1997, 40, 1347-1365.
    • Penning, T. D.; Talley, J. J.; Bertenshaw, S. R.; Carter, J. S.; Collins, P. W.; Doctor, S.; Graneto, M. J.; Lee, L. F.; Malecha, J. W.; Miyashiro, J. M.; Rogers, R. S.; Rogier, D. J.; Yu, S. S.; Anderson, G. D.; Burton, E. G.; Cogburn, J. N.; Gregory, S. A.; Koboldt, C. M.; Perkins, W. E.; Seibert, K.; Veenhuizen, A. W.; Zhang, Y. Y.; Isakson, P. C. 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., 1997, 40, 1347-1365.
  • 5
    • 0033526928 scopus 로고    scopus 로고
    • Prasit, P.; Wang, Z.; Brideau, C.; Chan, C. C.; Charleson, S.; Cromlish, W.; Ethier, D.; Evans, J. F.; Ford-Hutchinson, A. W.; Gauthier, J. Y.; Gordon, R.; Guay, J.; Gresser, M.; Kargman, S.; Kennedy, B.; Leblanc, Y.; Leger, S.; Mancini, J.; O_Neill, G. P.; Ouellet, M.; Percival, M. D.; Perrier, H.; Riendeau, D.; Rodger, I. W.; Tagari, P.; Therien, M.; Vickers, P.; Wong, E.; Xu, L.-J.; Young, R. N.; Zambani, R.; Boyce, S.; Rupniak, N.; Forest, M.; Visco, D.; Patrick, D. 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., 1999, 9, 1773-1778.
    • Prasit, P.; Wang, Z.; Brideau, C.; Chan, C. C.; Charleson, S.; Cromlish, W.; Ethier, D.; Evans, J. F.; Ford-Hutchinson, A. W.; Gauthier, J. Y.; Gordon, R.; Guay, J.; Gresser, M.; Kargman, S.; Kennedy, B.; Leblanc, Y.; Leger, S.; Mancini, J.; O_Neill, G. P.; Ouellet, M.; Percival, M. D.; Perrier, H.; Riendeau, D.; Rodger, I. W.; Tagari, P.; Therien, M.; Vickers, P.; Wong, E.; Xu, L.-J.; Young, R. N.; Zambani, R.; Boyce, S.; Rupniak, N.; Forest, M.; Visco, D.; Patrick, D. 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., 1999, 9, 1773-1778.
  • 7
    • 0028009093 scopus 로고
    • The X-ray crystal structure of the membrane protein prostaglandin H2 synthase-1
    • Picot, D.; Loll, P.J.; Gravito, R.M. The X-ray crystal structure of the membrane protein prostaglandin H2 synthase-1. Nature, 1994, 367, 243-249.
    • (1994) Nature , vol.367 , pp. 243-249
    • Picot, D.1    Loll, P.J.2    Gravito, R.M.3
  • 8
    • 0033031331 scopus 로고    scopus 로고
    • COX-2 inhibitors
    • Hawkey, C.J. COX-2 inhibitors. Lancet, 1999, 353, 307-314.
    • (1999) Lancet , vol.353 , pp. 307-314
    • Hawkey, C.J.1
  • 9
    • 0035960062 scopus 로고    scopus 로고
    • Three-dimensional quantitative structure-activity relationships of cyclooxygenase-2 (COX-2) inhibitors: A comparative molecular field analysis
    • Chavatte, P.; Yous, S.; Marot, C.; Baurin, N.; Lesieur, D. Three-dimensional quantitative structure-activity relationships of cyclooxygenase-2 (COX-2) inhibitors: a comparative molecular field analysis. J. Med. Chem., 2001, 44, 3223-3230.
    • (2001) J. Med. Chem , vol.44 , pp. 3223-3230
    • Chavatte, P.1    Yous, S.2    Marot, C.3    Baurin, N.4    Lesieur, D.5
  • 10
    • 0037364747 scopus 로고    scopus 로고
    • Cycloxygenase (COX) inhibitors: A comparative QSAR study
    • Garg, R.; Kurup, A.; Mekapati, S. B.; Hansch, C. Cycloxygenase (COX) inhibitors: a comparative QSAR study. Chem.Rev., 2003, 103, 703-731.
    • (2003) Chem.Rev , vol.103 , pp. 703-731
    • Garg, R.1    Kurup, A.2    Mekapati, S.B.3    Hansch, C.4
  • 11
    • 3042600821 scopus 로고    scopus 로고
    • Quantitative structure-activity relationship analysis of a series of 2,3-diaryl benzopyran analogues as novel selective cyclooxygenase-2 inhibitors
    • Prasanna, S.; Manivannan, E.; Chaturvedi, S.C. Quantitative structure-activity relationship analysis of a series of 2,3-diaryl benzopyran analogues as novel selective cyclooxygenase-2 inhibitors. Bioorg. Med. Chem. Lett., 2004, 14, 4005-4011.
    • (2004) Bioorg. Med. Chem. Lett , vol.14 , pp. 4005-4011
    • Prasanna, S.1    Manivannan, E.2    Chaturvedi, S.C.3
  • 12
    • 8844255455 scopus 로고    scopus 로고
    • QSAR analysis of 2,3-diaryl benzopyrans/pyrans as selective COX-2 inhibitors based on semiempirical AM1 Calculations
    • Prasanna, S.; Manivannan, E; Chaturvedi, S.C. QSAR analysis of 2,3-diaryl benzopyrans/pyrans as selective COX-2 inhibitors based on semiempirical AM1 Calculations. QSAR Comb. Sci., 2004, 23, 621-628.
    • (2004) QSAR Comb. Sci , vol.23 , pp. 621-628
    • Prasanna, S.1    Manivannan, E.2    Chaturvedi, S.C.3
  • 13
    • 4544314283 scopus 로고    scopus 로고
    • QSAR analysis of some fused pyrazoles as Cyclooxygenase inhibtors: A Hansch approach
    • Prasanna, S.; Manivannan, E.; Chaturvedi, S.C. QSAR analysis of some fused pyrazoles as Cyclooxygenase inhibtors: a Hansch approach. Arch. Pharm. Pharm. Med. Chem., 2004, 337, 440-444.
    • (2004) Arch. Pharm. Pharm. Med. Chem , vol.337 , pp. 440-444
    • Prasanna, S.1    Manivannan, E.2    Chaturvedi, S.C.3
  • 14
    • 10344222115 scopus 로고    scopus 로고
    • Rationalization of physico-chemical properties of 5,6-diarylthiazolo [3,2-b]-1,2,4-triazoles towards cyclooxygenase-2 (COX-2) inhibition
    • Manivannan, E.; Prasanna, S.; Chaturvedi, S.C. 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. Biophy., 2004, 41, 179-183.
    • (2004) Indian J. Biochem. Biophy , vol.41 , pp. 179-183
    • Manivannan, E.1    Prasanna, S.2    Chaturvedi, S.C.3
  • 15
    • 10644276950 scopus 로고    scopus 로고
    • QSAR studies on structurally similar 2-(4-methanesulfonylphenyl) pyran-4-ones as selective COX-2 inhibitors: A Hansch approach
    • Prasanna, S.; Manivannan, E.; Chaturvedi, S.C. QSAR studies on structurally similar 2-(4-methanesulfonylphenyl) pyran-4-ones as selective COX-2 inhibitors: a Hansch approach. Bioorg. Med. Chem. Lett., 2005, 15, 313-320.
    • (2005) Bioorg. Med. Chem. Lett , vol.15 , pp. 313-320
    • Prasanna, S.1    Manivannan, E.2    Chaturvedi, S.C.3
  • 16
    • 28244470051 scopus 로고    scopus 로고
    • Quantitative structure-activity relationship analysis of 2,3 diaryl indoles as selective cyclooxygenase-2 inhibitors
    • Prasanna, S.; Manivannan, E.; Chaturvedi SC. Quantitative structure-activity relationship analysis of 2,3 diaryl indoles as selective cyclooxygenase-2 inhibitors. J. Enzyme Inhib. Med. Chem., 2005, 20, 455-461.
    • (2005) J. Enzyme Inhib. Med. Chem , vol.20 , pp. 455-461
    • Prasanna, S.1    Manivannan, E.2    Chaturvedi, S.C.3
  • 17
    • 23244462984 scopus 로고    scopus 로고
    • Quantitative structure-activity relationship studies of cyclooxygenase inhibitors: A comprehensive analysis
    • Prasanna, S.; Manivannan, E.; Chaturvedi, S.C. Quantitative structure-activity relationship studies of cyclooxygenase inhibitors: a comprehensive analysis. Drug Dev. Res., 2005, 64, 220-231.
    • (2005) Drug Dev. Res , vol.64 , pp. 220-231
    • Prasanna, S.1    Manivannan, E.2    Chaturvedi, S.C.3
  • 18
    • 40749088834 scopus 로고    scopus 로고
    • Selective COX-2 inhibitors. Part 2: Synthesis and biological evaluation of 4-benzylideneamino- and 4-phenyliminomethyl-benzenesulfonamides
    • Lin, S-J.; Tsai, W-J.; Chiou, W-F.; Yang, T-H.; Yang, L-H. Selective COX-2 inhibitors. Part 2: synthesis and biological evaluation of 4-benzylideneamino- and 4-phenyliminomethyl-benzenesulfonamides. Bioorg. Med. Chem., 2008, 16, 2697-2706.
    • (2008) Bioorg. Med. Chem , vol.16 , pp. 2697-2706
    • Lin, S.-J.1    Tsai, W.-J.2    Chiou, W.-F.3    Yang, T.-H.4    Yang, L.-H.5
  • 20
    • 30244459245 scopus 로고
    • Testing for serial correlation in least squares regression II
    • Durbin, J.; Watson, G. S. Testing for serial correlation in least squares regression II. Biometrika, 1951, 38, 159-178.
    • (1951) Biometrika , vol.38 , pp. 159-178
    • Durbin, J.1    Watson, G.S.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.