Syntheses and evaluation of anti-inflammatory, analgesic and ulcerogenic activities of 1,3,4-oxadiazole and 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole derivatives

References

• Ray WA, Stein CM, Byrd V, Shorr R, Pichert JW, Gideon P et al. Educational program for physicians to reduce use of non-steroidal anti-inflammatory drugs among community-dwelling elderly persons: A randomized controlled trial. Med Care 2001;39:425–435.
   PubMed Web of Science ®Google Scholar
• Rang HP, Dale MM, Ritter JM, Flower RJ. Anti-inflammatory and immunosuppressant drugs. Rang and dale’s pharmacology. Elsevier Science Health Science div; 2007, pp. 227.
   Google Scholar
• Cocco MT, Congiu C, Onnis V, Morelli M, Cauli O. Synthesis of ibuprofen heterocyclic amides and investigation of their analgesic and toxicological properties. Eur j Med Chem 2003;38:513–518.
   PubMed Web of Science ®Google Scholar
• Dannhardt G, Kiefer W. Cyclooxygenase inhibitors–current status and future prospects. Eur j Med Chem 2001;36:109–126.
   PubMed Web of Science ®Google Scholar
• Marnett LJ, Kalgutkar AS. Design of selective inhibitors of cyclooxygenase-2 as nonulcerogenic anti-inflammatory agents. Curr Opin Chem Biol 1998;2:482–490.
   PubMed Web of Science ®Google Scholar
• Herrmann U, Laube W, Roth F, Schultheiss HR, Berger M, Schürmann P et al. Analgesic effect of fluproquazone in postoperative patients. Clin Pharmacol Ther 1980;27:379–385.
   Google Scholar
• Kurumbail RG, Stevens AM, Gierse JK, McDonald JJ, Stegeman RA, Pak JY et al. Structural basis for selective inhibition of cyclooxygenase-2 by anti-inflammatory agents. Nature 1996;384:644–648.
   PubMed Web of Science ®Google Scholar
• Prasit P, Wang Z, Brideau C, Chan CC, Charleson S, Cromlish W et al. The 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.
   PubMed Web of Science ®Google Scholar
• Isanbor C, O’Hagan D. Fluorine in medicinal chemistry: A review of anti-cancer agents. J Fluorine Chem 2006;127:303–319.
   Web of Science ®Google Scholar
• Karthikeyan MS, Holla BS, Kumari NS. Synthesis and antimicrobial studies on novel chloro-fluorine containing hydroxy pyrazolines. Eur j Med Chem 2007;42:30–36.
   PubMed Web of Science ®Google Scholar
• Karthikeyan MS, Prasad DJ, Mahalinga M, Holla BS, Kumari NS. Antimicrobial studies of 2,4-dichloro-5-fluorophenyl containing oxadiazoles. Eur j Med Chem 2008;43:25–31.
   PubMed Web of Science ®Google Scholar
• Shah P, Westwell AD. The role of fluorine in medicinal chemistry. j Enzyme Inhib Med Chem 2007;22:527–540.
   PubMed Web of Science ®Google Scholar
• Goel B, Ram T, Tyagi R, Bansal E, Kumar A, Mukherjee D, Sinha JN. 2-Substituted-3-(4-bromo-2-carboxyphenyl)-5-methyl-4-thiazolidinones as potential anti-inflammatory agents. Eur J Med Chem 1999;34:265–269.
   Web of Science ®Google Scholar
• Zheng X, Li Z, Wang Y, Chen W, Huang Q, Liu C, Song G. Syntheses and insecticidal activities of novel 2,5-disubstituted 1,3,4-oxadiazoles. J Fluorine Chem 2003;123:163–169.
   Web of Science ®Google Scholar
• Knutsen LJ, Hobbs CJ, Earnshaw CG, Fiumana A, Gilbert J, Mellor SL et al. Synthesis and SAR of novel 2-arylthiazolidinones as selective analgesic N-type calcium channel blockers. Bioorg Med Chem Lett 2007;17:662–667.
   PubMed Web of Science ®Google Scholar
• Bhandari SV, Bothara KG, Raut MK, Patil AA, Sarkate AP, Mokale VJ. Design, synthesis and evaluation of antiinflammatory, analgesic and ulcerogenicity studies of novel S-substituted phenacyl-1,3,4-oxadiazole-2-thiol and Schiff bases of diclofenac acid as nonulcerogenic derivatives. Bioorg Med Chem 2008;16:1822–1831.
   PubMed Web of Science ®Google Scholar
• Chen CJ, Song BA, Yang S, Xu GF, Bhadury PS, Jin LH et al. Synthesis and antifungal activities of 5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-thiadiazole and 5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-oxadiazole derivatives. Bioorg Med Chem 2007;15:3981–3989.
   PubMed Web of Science ®Google Scholar
• Ali MA, Shaharyar M. Oxadiazole mannich bases: Synthesis and antimycobacterial activity. Bioorg Med Chem Lett 2007;17:3314–3316.
   PubMed Web of Science ®Google Scholar
• Aboraia AS, Abdel-Rahman HM, Mahfouz NM, El-Gendy MA. Novel 5-(2-hydroxyphenyl)-3-substituted-2,3-dihydro-1,3,4-oxadiazole-2-thione derivatives: Promising anticancer agents. Bioorg Med Chem 2006;14:1236–1246.
   PubMed Web of Science ®Google Scholar
• Joshi SD, Vagdevi HM, Vaidya VP, Gadaginamath GS. Synthesis of new 4-pyrrol-1-yl benzoic acid hydrazide analogs and some derived oxadiazole, triazole and pyrrole ring systems: A novel class of potential antibacterial and antitubercular agents. Eur j Med Chem 2008;43:1989–1996.
   PubMed Web of Science ®Google Scholar
• Amir M, Kumar H, Javed SA. Synthesis and pharmacological evaluation of condensed heterocyclic 6-substituted-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole derivatives of naproxen. Bioorg Med Chem Lett 2007;17:4504–4508.
   PubMed Web of Science ®Google Scholar
• Holla BS, Poojary KN, Rao BS, Shivananda MK. New bis-aminomercaptotriazoles and bis-triazolothiadiazoles as possible anticancer agents. Eur j Med Chem 2002;37:511–517.
   PubMed Web of Science ®Google Scholar
• Methew V, Keshavayya J, Vaidya VP. Heterocyclic system containing bridgehead nitrogen atom: Synthesis and pharmacological activities of some substituted 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles. Eur J Med Chem 2006;41:1048–1058.
   Google Scholar
• Chandrakantha B, Shetty P, Nambiyar V, Isloor N, Isloor AM. Synthesis, characterization and biological activity of some new 1,3,4-oxadiazole bearing 2-flouro-4-methoxy phenyl moiety. Eur j Med Chem 2010;45:1206–1210.
   PubMed Web of Science ®Google Scholar
• Husain A, Ahmad A, Alam MM, Ajmal M, Ahuja P. Fenbufen based 3-[5-(substituted aryl)-1,3,4-oxadiazol-2-yl]-1-(biphenyl-4-yl)propan-1-ones as safer antiinflammatory and analgesic agents. Eur j Med Chem 2009;44:3798–3804.
   PubMed Web of Science ®Google Scholar
• Palaska E, Sahin G, Kelicen P, Durlu NT, Altinok G. Synthesis and anti-inflammatory activity of 1-acylthiosemicarbazides, 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazole-3-thiones. Farmaco 2002;57:101–107.
   PubMedGoogle Scholar
• Karegoudar P, Prasad DJ, Ashok M, Mahalinga M, Poojary B, Holla BS. Synthesis, antimicrobial and anti-inflammatory activities of some 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles and 1,2,4-triazolo[3,4-b][1,3,4]thiadiazines bearing trichlorophenyl moiety. Eur j Med Chem 2008;43:808–815.
   PubMed Web of Science ®Google Scholar
• Akhter M, Husain A, Azad B, Ajmal M. Aroylpropionic acid based 2,5-disubstituted-1,3,4-oxadiazoles: Synthesis and their anti-inflammatory and analgesic activities. Eur j Med Chem 2009;44:2372–2378.
   PubMed Web of Science ®Google Scholar
• Sun XY, Hu C, Deng XQ, Wei CX, Sun ZG, Quan ZS. Synthesis and anti-inflammatory activity evaluation of some novel 6-alkoxy(phenoxy)-[1,2,4]triazolo[3,4-a]phthalazine-3-amine derivatives. Eur j Med Chem 2010;45:4807–4812.
   PubMed Web of Science ®Google Scholar
• Carson JL, Strom BL, Morse ML, West SL, Soper KA, Stolley PD et al. The relative gastrointestinal toxicity of the nonsteroidal anti-inflammatory drugs. Arch Intern Med 1987;147:1054–1059.
   PubMed Web of Science ®Google Scholar
• Chambers R, Skinner C, Atherton M, Moilliet J. Halogenation Reactions. US Patent, 667, 088 (2001).
   Google Scholar
• Winter CA, Risley EA, Nuss GW. Carrageenin-induced edema in hind paw of the rat as an assay for antiiflammatory drugs. Proc Soc Exp Biol Med 1962;111:544–547.
   PubMed Web of Science ®Google Scholar
• Siegmund E, Cadmus R, Lu G. A method for evaluating both non-narcotic and narcotic analgesics. Proc Soc Exp Biol Med 1957;95:729–731.
   PubMed Web of Science ®Google Scholar
• Cioli V, Putzolu S, Rossi V, Scorza Barcellona P, Corradino C. The role of direct tissue contact in the production of gastrointestinal ulcers by anti-inflammatory drugs in rats. Toxicol Appl Pharmacol 1979;50:283–289.
   PubMed Web of Science ®Google Scholar
• Ohkawa H, Ohishi N, Yagi K. Assay for lipid peroxides in animal tissues by thiobarbituric acid reaction. Anal Biochem 1979;95:351–358.
   PubMed Web of Science ®Google Scholar
• Bekhit AA, Fahmy HT. Design and synthesis of some substituted 1H-pyrazolyl-oxazolidines or 1H-pyrazolyl-thiazolidines as anti-inflammatory-antimicrobial agents. Arch Pharm (Weinheim) 2003;336:111–118.
   PubMed Web of Science ®Google Scholar
• Harrison JJ, Pellegrini JP, Selwitz CM. Bromination of deactivated aromatics using potassium bromate. J Org Chem 1981;46:2169–2171.
   Google Scholar