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Synthesis and Antiinflammatory-analgesic Activity of Monovalent and Bivalent Aminoantipyrines  

김승재 (중앙대학교 약학대학 의약품화학교실)
권오혁 (중앙대학교 약학대학 의약품화학교실)
전상철 (중앙대학교 약학대학 의약품화학교실)
박상민 (중앙대학교 약학대학 의약품화학교실)
임채욱 (중앙대학교 약학대학 의약품화학교실)
임철부 (중앙대학교 약학대학 의약품화학교실)
Publication Information
YAKHAK HOEJI / v.46, no.3, 2002 , pp. 149-154 More about this Journal
Abstract
Six novel 4-aminoantipyrine derivatives as potential nonsteroidal antiinflammatory and analgesic compounds were prepared and their antiinflammatory-analgesic activity were compared with antiprine. Succinyl chloride and Ac $_2$O were reacted with glycine, respectively, to give glycine compounds (3-4, 9-10), which were treated with hydroxysuccinimide and dicyclohexyl carbodiimide to yield active esters (5-6, 11-12), and then reacted with 4-aminoantipyrine to prepare 4-aminoantipyrine derivatives (7-8, 13-14). 4-Aminoantipyrine reacted with succinyl chloride and Ac $_2$O, respectively, to give succinyl bis aminoantipyrine (15) and acetyl aminoantipyrine (16). Compounds (7), (8) and (13) gave comparable antiinflammatory activity to antipyrine.
Keywords
Antipyrine amide; analgesic agents; antiinflammatory agents;
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1 Rang, H. P., Dale, M. M. and Ritter, J. M. : Pharmacology, Churchill living-stone 3rd ed., 251 (1996)
2 Lombardino, J. G. : Nonsteroidal Antiinflammatory Drugs, John Wiley & Sons, New York, 1st ed. (1985)
3 Baraka, Y. M. and Bekemeier, H. : Antiinflammatory activity of 4-anisylidino(aminoantipyrine) in the carrageenin paw edema of the rat. J. Drug Res. 9(2), 183 (1977)
4 Winter, C. A., Riskey; E. A. and Nuss, G. W. : Carrageenininduced edema in hind paw of the rat as an assay for antiinflammatory drugs. Proc. Soc. Exp. Med. 111, 544 (1962)
5 Burdulene, D., Palaima, A., Stumbryavichyute, Z. and Talaikite, Z. : Synthesis and antiinflarnmatory activity of 4-aminoantipyrine derivatives of succinamides. Pharmaceutical Chemistry Journal 33(4), 191 (2000)
6 Sondhi, S. M., Sharma, V. K., Verma, R. P., Singhal, N., Shukla, R., Raghubir, R., Dubey, M. P. : Synthesis, anti-inflammatory, and analgesic activity evaluation of some mercapto pyrimidine and pyrimidobenzimidazole derivatives. Synthesis 5, 878 (1999)
7 Hammouda,M. : Synthesis of some new 4-substituted antipyrines as potential antipyretic analgesics. Arch. Pharmacal Res. 15(1), 1 (1992)
8 Khamees, H. A., Bayomi, S. M., Kandil, H. A. and Tahir, K. E.: Synthesis and pharmacological screening of a new series of 3( 4-antipyryl)-2-arylthiazolidin-4-ones. Eur. J. Med. Chem. 25(2), 103 (1990)
9 Portoghese, P. S., Larson, D. L., Yim, C. B., Sayre, L. M., Ronsisvall, G., Tam, S. W. and Takemori, A. Z. : Opioid agonist and antagonist bivalent ligands. The relationship between spacer length and selectivity at multiple opioid receptors. J. Med. Chem. 29, 1885 (1986)
10 Erez, M., Takemori, A. E. and Portoghese: Narcotic antagonistic potency of bivalent ligands which contain beta-naltrexamine. Evidence for bridging between proximal recognition sites. J. Med. Chem. 25, 847 (1982)
11 Fujimoto, Yasuo.: 4-Pyridoxylideneaminoantipyrine. Jpn. Kokai Tokkyo Koho, JP 49024972 19740305 Showa. (1974)
12 Koster, R., Anderson, M. and De Beer, E. J,: Acetic acid for analgesic screening. Fed. Proc. 18, 412 (1985)
13 Buchanan, W. W. and Kean, W. F. : Current Nonsteroidal Antiinflammatory Drug Therapy in Rheumatoid Arthritis, with Emphasis on Use in the Elderly, Nonsteroidal Antiinflammatary Drugs, Marcel Dekker, 9 (1987)