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Volumn 45, Issue 6, 1997, Pages 987-995

Studies on anti-inflammatory agents. IV. Synthesis and pharmacological properties of 1,5-diarylpyrazoles and related derivatives

Author keywords

1,5 diarylpyrazole; Anti inflammatory agent; Cyclooxygenase; Structure activity relationship; Synthesis

Indexed keywords

4' ACETYL 2' (2,4 DIFLUOROPHENOXY)METHANESULFONANILIDE; 5 (4 FLUOROPHENYL) 1 [(4 METHYLSULFONYL)PHENYL] 3 TRIFLUOROMETHYLPYRAZOLE; 5 BROMO 2 (4 FLUOROPHENYL) 3 (4 METHYLSULFONYLPHENYL)THIOPHENE; ANTIINFLAMMATORY AGENT; CYANIDE; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; NONSTEROID ANTIINFLAMMATORY AGENT; PROSTAGLANDIN E2; PROSTAGLANDIN SYNTHASE INHIBITOR; PYRAZOLE DERIVATIVE;

EID: 0030860775     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.45.987     Document Type: Article
Times cited : (48)

References (28)
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    • note
    • Compound 1 was metabolized to a 5-(methylsulfonyl)thiophene derivative in rats. Compound 1 also showed mutagenicity in a chromosome aberration test conducted by Toxicology Research Laboratories, Fujisawa Pharmaceutical Co., Ltd. (unpublished results).
  • 14
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    • note
    • The energy levels and the orbital distributions of HOMO and LUMO, and the torsion angles of the benzene rings of the most stable conformer of 5-bromo-3-(4-acetylphenyl)-2-(4-fluorophenyl)thiophene (38) and that of 3-bromo-5-(4-acetylphenyl)-1-(4-fluorophenyl)pyrazole (39) were calculated by the MNDO method: e.g., the torsion angle of the 4-acetylphenyl ring was +77.7° (38) and +79.1° (39) and that of the 4-fluorophenyl ring was +77.4° (38) and +77.3° (39), respectively.
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    • note
    • The production of the by-product 15 was suppressed when the reaction was conducted in AcOH.
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    • Manuscript in preparation.
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    • COX-2 inhibitors having a sulfonamide group were recently reported: a) Li J. J., Anderson G. D., Burton E. G., Cogburn J. N., Collins J. T., Garland D. J., Gregory S. A., Huang H.-C., Isakson P. C., Koboldt C. M., Logusch E. W., Norton M. B., Perkins W. E., Reinhard E. J., Seibert K., Veenhuizen A. W., Zhang Y., Reitz D. B., J. Med. Chem., 38, 4570-4578 (1995); b) Leblanc Y., Gauthier J. Y., Ethier D., Guay J., Mancini J., Riendeau D., Tagari P., Vickers P., Wong E., Prasit P., Bioorg. Med. Chem. Lett., 5, 2123-2128 (1995).
    • (1995) Bioorg. Med. Chem. Lett. , vol.5 , pp. 2123-2128
    • Leblanc, Y.1    Gauthier, J.Y.2    Ethier, D.3    Guay, J.4    Mancini, J.5    Riendeau, D.6    Tagari, P.7    Vickers, P.8    Wong, E.9    Prasit, P.10
  • 24
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    • note
    • COX-1 inhibition at 100 μM: 0% (33), 8% (37); COX-2 inhibition at 100 μM: 19% (33), 49% (37).
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    • note
    • This product was used for the next step in the synthesis without further purification.
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    • note
    • Supplied by Exploratory Research Laboratories, Fujisawa Pharmaceutical Co., Ltd. (Tsukuba, Ibaraki).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.