메뉴 건너뛰기




Volumn 57, Issue 1, 2007, Pages 13-30

Studies in 3,4-diaryl-1,2,5-oxadiazoles and their N-oxides: Search for better COX-2 inhibitors

Author keywords

1,2,5 oxadiazole; 1,2,5 oxadiazole N oxide; COX 2 inhibitor

Indexed keywords

3,4 DI(4 METHOXYPHENYL) 1,2,5 OXADIAZOLE N OXIDE; 3,4 DIARY 1,2,5 OXADIAZOLE; 3,4 DIARY 1,2,5 OXADIAZOLE N OXIDE; CELECOXIB; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITOR; OXADIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33847644608     PISSN: 13300075     EISSN: None     Source Type: Journal    
DOI: 10.2478/v10007-007-0002-z     Document Type: Article
Times cited : (28)

References (22)
  • 1
    • 2142695733 scopus 로고    scopus 로고
    • Cyclooxygenases: New forms, new inhibitors, and lessons from the clinic
    • T. D. Warner and J. A. Mitchell, Cyclooxygenases: new forms, new inhibitors, and lessons from the clinic, FASEB J. 18 (2004) 790-804.
    • (2004) FASEB J , vol.18 , pp. 790-804
    • Warner, T.D.1    Mitchell, J.A.2
  • 2
    • 23244445988 scopus 로고    scopus 로고
    • Cyclooxygenase inhibition and cardiovascular risk
    • E. M. Antman, D. DeMets and J. Loscalzo, Cyclooxygenase inhibition and cardiovascular risk, Circulation 112 (2005) 759-770.
    • (2005) Circulation , vol.112 , pp. 759-770
    • Antman, E.M.1    DeMets, D.2    Loscalzo, J.3
  • 4
    • 85176837996 scopus 로고    scopus 로고
    • T. D. Penning, J. J. Talley, S. R. Bertenshaw, J. S. Carter, P. W. Collins, S. Docter, M. J. Graneto, F. J. Lee, J. W. Malecha, J. M. Miyashiro, R. S. Rogers, D. J. Rogier, S. S. Yu, G. A. Anderson, F. G. Burton, J. N. Cogburn, S. A. Gragory, C. M. Koboldt, W. E. Perkins, K. Seibert, A. W. Veenhuizen, Y. Y. Zhang and P. C. Isakson, Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: Identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl) -1H-pyrazol-1-yl]benzenesulfonamide (SC-58635, Celecoxib), J. Med. Chem. 40 (1997) 1347-1365.
    • T. D. Penning, J. J. Talley, S. R. Bertenshaw, J. S. Carter, P. W. Collins, S. Docter, M. J. Graneto, F. J. Lee, J. W. Malecha, J. M. Miyashiro, R. S. Rogers, D. J. Rogier, S. S. Yu, G. A. Anderson, F. G. Burton, J. N. Cogburn, S. A. Gragory, C. M. Koboldt, W. E. Perkins, K. Seibert, A. W. Veenhuizen, Y. Y. Zhang and P. C. Isakson, Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: Identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl) -1H-pyrazol-1-yl]benzenesulfonamide (SC-58635, Celecoxib), J. Med. Chem. 40 (1997) 1347-1365.
  • 5
    • 0035246513 scopus 로고    scopus 로고
    • Cyclooxygenase inhibitors - current status and future prospects
    • G. Dannhardt and W. Kiefer, Cyclooxygenase inhibitors - current status and future prospects, Eur. J. Med. Chem. 36 (2001) 109-126.
    • (2001) Eur. J. Med. Chem , vol.36 , pp. 109-126
    • Dannhardt, G.1    Kiefer, W.2
  • 6
    • 85176849549 scopus 로고    scopus 로고
    • P. Prasit, Z. Wang, C. Brideau, C. C. Chan, S. Charleson, W. Cromlish, D. Either, J. F. Evans, A. W. Ford-Hutchinson, J. Y. Gauthier, R. Gordon, J. Guay, M. Gresser, S. Kargman, B. Kennedy, Y. Leblanc, S. Leger, J. Mancini, G. P. O'Neil, M. Ouellet, M. D. Percieval, H. Perrier, D. Riendeau, I. Rodger, P. Tagari, M. Therien, P. Vickers, E. Wong, L. J. Xu, R. N. Young, R. Zamboni, S. Boyce, N. Rupniak, M. Forrest, D. Visco and D. Patrick, The discovery of rofecoxib, [MK 966, VIOXX®, 4-(4′-methylsulfonylphenyl)-3-phenyl- 2(5H)-furanone], an orally active cyclooxy-genase-2 inhibitor, Bioorg. Med. Chem. Lett. 9 (1999) 1773-1778.
    • P. Prasit, Z. Wang, C. Brideau, C. C. Chan, S. Charleson, W. Cromlish, D. Either, J. F. Evans, A. W. Ford-Hutchinson, J. Y. Gauthier, R. Gordon, J. Guay, M. Gresser, S. Kargman, B. Kennedy, Y. Leblanc, S. Leger, J. Mancini, G. P. O'Neil, M. Ouellet, M. D. Percieval, H. Perrier, D. Riendeau, I. Rodger, P. Tagari, M. Therien, P. Vickers, E. Wong, L. J. Xu, R. N. Young, R. Zamboni, S. Boyce, N. Rupniak, M. Forrest, D. Visco and D. Patrick, The discovery of rofecoxib, [MK 966, VIOXX®, 4-(4′-methylsulfonylphenyl)-3-phenyl- 2(5H)-furanone], an orally active cyclooxy-genase-2 inhibitor, Bioorg. Med. Chem. Lett. 9 (1999) 1773-1778.
  • 8
    • 0034030366 scopus 로고    scopus 로고
    • N-[[(5-Methyl-3-phenylisoxazol-4-yl)-phenyl]sulfonyl]propanamide, sodium salt, parecoxib sodium: A potent and selective inhibitor of COX-2 for parenteral administration
    • J. J. Tally, S. R. Bertenshaw, D. L. Brown, J. S. Carter, M. J. Graneto, M. S. Kellogg, C. M. Koboldt, J. Yuan, Y. Y. Zhang and K. Seibert, N-[[(5-Methyl-3-phenylisoxazol-4-yl)-phenyl]sulfonyl]propanamide, sodium salt, parecoxib sodium: A potent and selective inhibitor of COX-2 for parenteral administration, J. Med. Chem. 43 (2000) 1661-1663.
    • (2000) J. Med. Chem , vol.43 , pp. 1661-1663
    • Tally, J.J.1    Bertenshaw, S.R.2    Brown, D.L.3    Carter, J.S.4    Graneto, M.J.5    Kellogg, M.S.6    Koboldt, C.M.7    Yuan, J.8    Zhang, Y.Y.9    Seibert, K.10
  • 10
    • 85176837760 scopus 로고    scopus 로고
    • M. R. Yadav, R. Giridhar and H. B. Prajapati, A Process for Preparation of 3-[o-/m-/p-Mono/DisubstitutedPhenyl]-4-[o-/p-Substitutedphenyl] furazans and Furoxans, Indian Patent Appl. No. 109/MUM/2004, Feb. 2004
    • M. R. Yadav, R. Giridhar and H. B. Prajapati, A Process for Preparation of 3-[o-/m-/p-Mono/DisubstitutedPhenyl]-4-[o-/p-Substitutedphenyl] furazans and Furoxans, Indian Patent Appl. No. 109/MUM/2004, Feb. 2004.
  • 11
    • 12344273021 scopus 로고    scopus 로고
    • Pharmacological properties of furoxans and benzofuroxans: Recent developments
    • H. Cerecetto and W. Porcal, Pharmacological properties of furoxans and benzofuroxans: Recent developments, Mini-Rev. Med. Chem. 5 (2005) 57-71.
    • (2005) Mini-Rev. Med. Chem , vol.5 , pp. 57-71
    • Cerecetto, H.1    Porcal, W.2
  • 12
    • 0141611660 scopus 로고    scopus 로고
    • Nitric oxide synthase inhibitors: Biology and Chemistry
    • V. G. Granik and N. B. Grigor, Nitric oxide synthase inhibitors: Biology and Chemistry, Russ. Chem. Bull. 51 (2002) 1973-1995.
    • (2002) Russ. Chem. Bull , vol.51 , pp. 1973-1995
    • Granik, V.G.1    Grigor, N.B.2
  • 13
    • 15244340003 scopus 로고    scopus 로고
    • 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
    • C. Velazquez, P. N. P. Rao, R. McDonald and E. E. Knaus, 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. 13 (2005) 2749-2757.
    • (2005) Bioorg. Med. Chem , vol.13 , pp. 2749-2757
    • Velazquez, C.1    Rao, P.N.P.2    McDonald, R.3    Knaus, E.E.4
  • 14
  • 15
    • 0011939626 scopus 로고
    • Mixed benzoins. II
    • J. S. Buck and W. S. Ide, Mixed benzoins. II, J. Am. Chem. Soc. 52 (1930) 4107-4109.
    • (1930) J. Am. Chem. Soc , vol.52 , pp. 4107-4109
    • Buck, J.S.1    Ide, W.S.2
  • 16
    • 33744790617 scopus 로고    scopus 로고
    • An efficient and time saving microwave assisted selenium dioxide oxidation of 1,2-diarylethanones
    • S. T. Shirude, P. Patel, R. Giridhar and M. R. Yadav, An efficient and time saving microwave assisted selenium dioxide oxidation of 1,2-diarylethanones, Indian. J. Chem. 45B (2006) 1080-1085.
    • (2006) Indian. J. Chem , vol.45 B , pp. 1080-1085
    • Shirude, S.T.1    Patel, P.2    Giridhar, R.3    Yadav, M.R.4
  • 17
    • 16244383547 scopus 로고    scopus 로고
    • Design and synthesis of subtype-selective cyclooxygenase (COX) inhibitors derived from thalidomide
    • H. Sano, T. Noguchi, A. Tanatani, Y. Hashimoto and H. Miyachi, Design and synthesis of subtype-selective cyclooxygenase (COX) inhibitors derived from thalidomide, Bioorg. Med. Chem. 13 (2005) 3079-3091.
    • (2005) Bioorg. Med. Chem , vol.13 , pp. 3079-3091
    • Sano, H.1    Noguchi, T.2    Tanatani, A.3    Hashimoto, Y.4    Miyachi, H.5
  • 18
    • 67249094291 scopus 로고
    • Carrageenin-induced edema in hind paw of the rat as an assay for antiinflammatory drugs
    • C. A. Winter, E. A. Risley and G. W. Nuss, Carrageenin-induced edema in hind paw of the rat as an assay for antiinflammatory drugs, Proc. Soc. Exp. Biol. Med. 111 (1962) 544-547.
    • (1962) Proc. Soc. Exp. Biol. Med , vol.111 , pp. 544-547
    • Winter, C.A.1    Risley, E.A.2    Nuss, G.W.3
  • 19
    • 85176828903 scopus 로고    scopus 로고
    • SYBYL Molecular modeling system, version 6.9, Tripos, Inc, St. Louis, USA, 2003
    • SYBYL Molecular modeling system, version 6.9, Tripos, Inc., St. Louis, USA, 2003.
  • 21
    • 84988115618 scopus 로고
    • Validation of the General-Purpose Tripos 5.2 force field
    • M. Clark, R. D. Crammer and N. van Opdenbosh, Validation of the General-Purpose Tripos 5.2 force field, J. Comput. Chem. 10 (1989) 982-1012.
    • (1989) J. Comput. Chem , vol.10 , pp. 982-1012
    • Clark, M.1    Crammer, R.D.2    van Opdenbosh, N.3
  • 22
    • 0000821456 scopus 로고
    • The transformation of ψ-o-dinitroso aromatic compounds into o-nitroaryl amines
    • J. H. Boyer, R. F. Reinisch, M. J. Danzig, G. A. Stoner and F. Sahhar, The transformation of ψ-o-dinitroso aromatic compounds into o-nitroaryl amines, J. Am. Chem. Soc. 77 (1955) 5688-5690.
    • (1955) J. Am. Chem. Soc , vol.77 , pp. 5688-5690
    • Boyer, J.H.1    Reinisch, R.F.2    Danzig, M.J.3    Stoner, G.A.4    Sahhar, F.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.