Synthesis of some imidazolyl-thioacetyl-pyrazolinone derivatives and their antinociceptive and anticancer activities

References

• Pariet M, Ryn JV. COX-2 Inhibitors. Berlin: Birkhauser Verlag, 2004:15–40, 227–43.
   Google Scholar
• Talley JJ. Selective inhibitors of cyclooxygenase-2. Prog Med Chem 1999;36: 201–34.
   PubMed Web of Science ®Google Scholar
• Leval X, Delarge J, Somers F, Tullio P, Henrotin Y, Pirotte B, et al. Recent advances in inducible cyclooxygenase (COX-2) inhibition. Curr Med Chem 2000;7:1041–62.
   PubMed Web of Science ®Google Scholar
• Dannhardt G, Kiefer W. Cyclooxygenase inhibitors—current status and future prospects. Eur J Med Chem 2001;36:109–26.
   PubMed Web of Science ®Google Scholar
• Penning TD, Talley JJ, Bertenshaw SR, Carter JS, Collins PW, Docter S, et al. Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: identification of 4-5-(4-metylphenyl)-3-(trifluorometyl)-1h-pyrazol-1-yl-benzenesulfonamide (sc-58635, celecoxib). J Med Chem 1997;40:1347–65.
   PubMed Web of Science ®Google Scholar
• Khanna IK, Weier RM, Yu Y, Collins PW, Miyashiro JM, Koboldt CM, et al. 1,2-Diarylpyrroles as potent and selective inhibitors of cyclooxygenase-2. J Med Chem 1997;40:1619–33.
   PubMed Web of Science ®Google Scholar
• Talley JJ, Brown DL, Carter JS, Graneto MJ, Koboldt CM, Masferrer JL, et al. 4-[5-Methyl-3-phenylisoxazol-4-yl]-benzenesulfonamide, valdecoxib: a potent and selective inhibitor of COX-2. J Med Chem 2000;43:775–7.
   PubMed Web of Science ®Google Scholar
• Habeeb AG, Rao PNP, Knaus EE. Design and syntheses of diarylisoxazoles: novel inhibitors of cyclooxygenase-2 (COX-2) with analgesic-antiinflammatory activity. Drug Dev Res 2000;51:273–86.
   Web of Science ®Google Scholar
• Almansa C, Arriba AF, Cavalcanti FL, Gomez LA, Miralles A, Merios M, et al. Synthesis and SAR of a new series of COX-2-selective inhibitors: pyrazolo[1,5-a]pyrimidines. J Med Chem 2001;44:350–61.
   PubMed Web of Science ®Google Scholar
• Hashimoto H, Imamura K, Haruta J, Wakitani K. 4-(4-Cycloalkyl/aryl-oxazol-5-yl)benzenesulfonamides as selective by introduction of a fluorine atom and identification of a potent, highly selective, an orally active COX-2 inhibitor jte-522. J Med Chem 2002;45:1511–17.
   PubMed Web of Science ®Google Scholar
• Laufer SA, Wagner GK. From imidazoles to pyrimidines: new inhibitors of cytokine release. J Med Chem 2002;45:2733–40.
   PubMed Web of Science ®Google Scholar
• Liu H, Huang X, Shen J, Luo X, Li M, Xiong B, et al. Inhibitory mode of 1,5-diarylpyrazole derivatives against cyclooxygenase-2 and cyclooxygenase-1: molecular docking and 3D QSAR analyses. J Med Chem 2002;45:4816–27.
   PubMed Web of Science ®Google Scholar
• Almansa C, Alfon J, Arriba A, Cavalcanti FL, Escamilla I, Gomez LA, et al. Synthesis and structure-activity relationship of a new series of COX-2 selective inhibitors: 1,5-diarylimidazoles. J Med Chem 2003;46:3463–75.
   PubMed Web of Science ®Google Scholar
• Rao PNP, Amini M, Li H, Habeeb AG, Knaus EE. Design, synthesis, and biological evaluation of 6-substituted-3-(4-methanesulfonylphenyl)-4-phenylpyran-2-ones: a novel class of diarylheterocyclic selective cyclooxygenase-2-inhibitors. J Med Chem 2003;46:4872–82.
   PubMed Web of Science ®Google Scholar
• Hu W, Guo Z, Chu F, Bai A, Yi X, Cheng G, et al. Synthesis and biological evaluation of substituted 2-sulfonyl-phenyl-3-phenyl-indoles: a new series of selective COX-2 inhibitors. Bioorg Med Chem 2003;11:1153–60.
   PubMed Web of Science ®Google Scholar
• Singh SK, Vobbalareddy S, Shivaramakrishna S, Krishnamraju A, Rajjak SA, Casturi SR, et al. Methanesulfonamide group at position-4 of the c-5-phenyl ring of 1,5-diarylpyrazole affords as a potent class of cyclooxygenase-2 (COX-2) inhibitors. Bioorg Med Chem Lett 2004;14:1683–8.
   PubMed Web of Science ®Google Scholar
• Tuyen TN, Sin K, Kim HP, Park H. Synthesis and antiinflammatory activity of 1,5-diarylimidazoles. Arch Pharm Res 2005;28:1013–18.
   PubMed Web of Science ®Google Scholar
• Mozziconacci J, Arnoult E, Bernard P, Do QT, Marot C, Morin-Allory L. Optimization and validation of a docking-scoring protocol; application to virtual screening for COX-2 inhibitors. J Med Chem 2005;48:1055–68.
   PubMed Web of Science ®Google Scholar
• Laufer SA, Zimmermann W, Ruff KJ. Tetrasubstituted imidazole inhibitors of cytokine release: probing substituents in the n-1 position. J Med Chem 2004;47:6311–25.
   PubMed Web of Science ®Google Scholar
• Navidpour L, Shadnia H, Shafaroodi H, Amini M, Dehpour AR, Shafiee A. Design, synthesis and biological evaluation of substituted 2-alkylthio-1,5-diarylimidazoles as selective COX-2 inhibitors. Bioorg Med Chem 2007;15:1976–82.
   PubMed Web of Science ®Google Scholar
• Borne RF. Nonsteroidal antiinflammatory drugs. In: Foye WO, Lemke TL, Williams DA, eds. Principles of Medicinal Chemistry, 4th ed. Philadelphia, PA: Williams & Wilkins, 1995:535–80.
   Google Scholar
• Hida T, Kozaki K, Muramatsu H, Masuda A, Shimizu S, Mitsudomi T, et al. Cyclooxygenase-2 inhibitor induces apoptosis and enhances cytotoxicity of various anticancer agents in non-small cell lung cancer cell lines. Clin Cancer Res 2000;6:2006–11.
   PubMed Web of Science ®Google Scholar
• Petersen C, Baumann M, Petersen S. New targets for the modula- tion of radiation response-selective inhibition of the enzyme cyclo- oxygenase 2. Curr Med Chem Anticancer Agents 2003; 3:354–9.
   PubMedGoogle Scholar
• Gust R, Busch S, Keilitz R, Schmidt K, Rauch M. Investigations on the influence of halide substituents on the estrogen receptor interaction of 2,4,5-tris(4-hydroxyphenyl)imidazoles. Arch Pharm Pharm Med Chem 2003;336:456–65.
   PubMed Web of Science ®Google Scholar
• Ye F, Wu J, Dunn T, Yi J, Tong X, Zhang D. Inhibition of clclooxygenase-2 activity in head and neck cancer cells by genistein. Cancer Lett 2004;211:39–46.
   PubMed Web of Science ®Google Scholar
• Johnsen JI, Lindskog M, Ponthan F, Pettersen I, Elfman L, Orrego A. Cyclooxygenase-2 is expressed in neuroblastoma, and nonsteroidal anti-inflammatory drugs induce apoptosis and inhibit tumor growth in vivo. Cancer Res 2004;64:7210–15.
   PubMed Web of Science ®Google Scholar
• Kaufmann HP, Huang S, Buckmann HJ. über antipyril-ketone. Berichte 1942;75B:1214.
   Google Scholar
• Korohoda MJ, Bojarska AB. Methylation of 4-imidazoline-2-thiones. J Prakt Chem 1991;333:355–60.
   Google Scholar
• Biancchi C, Franceschini J. Experimental observations on Haffners method for testing analgesic drugs. Br J Pharmacol 1954;9:280–4.
   Web of Science ®Google Scholar
• Eddy NB, Leimbach D. Synthetic analgesic (II). Dithienylbutenyl- and dithienylbutylamines. J Pharmacol Exp Ther 1953;107:385–93.
   PubMed Web of Science ®Google Scholar
• Noble F, Smadja C, Roques BP. Role of endogenous cholecystokinin in the facilitation of mu-mediated antinociception by delta opioid agonists. J Pharmacol Exp Ther 1994;271:1127–34.
   PubMed Web of Science ®Google Scholar
• Bastos GNT, Santos ARS, Ferreira VMM, Costa AMR, Bispo CI, Silveira AJA, et al. Antinociceptive effect of aqueous extract obtained from roots of physalis angulata L. on mice. J Ethnopharmacol 2006;103:241–5.
   PubMed Web of Science ®Google Scholar
• Koster R, Anderson M, Beer EJ. Acetic acid for analgesic screening. Fed Proc 1959;18:412.
   Google Scholar
• Boyd MR. Status of the NCI preclinical antitumor drug discovery screen. Princ Pract Oncol 1989;3:2–11.
   Google Scholar
• Gürsoy A, Demirayak S, Capan G, Erol K, Vural K. Synthesis and preliminary evaluation of new 5-pyrazolinone derivatives as analgesic agents. Eur J Med Chem 2000;35:359–64.
   PubMed Web of Science ®Google Scholar