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Research Article

Synthesis of some pyrazolyl benzenesulfonamide derivatives as dual anti-inflammatory antimicrobial agents

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Pages 296-309 | Received 19 Nov 2007, Accepted 17 Mar 2008, Published online: 01 Feb 2009

References

  • JM Scheiman. (2005). Effects of nonsteroidal anti-inflammatory drugs, including COX-2 specific inhibitors on the GI tract. Clin Update 12:1–4.
  • S Fiorucci, L Santucci, and E Distrutti. (2007). NSAIDs, coxibs, CINOD and H2S-releasing NSAIDs: What lies beyond the horizon. Digest Liver Dis 39:1043–1051.
  • DC Kosegarten, EF LaSala, SF Long In: , L Shargel, AH Mutnick, PF Souncy, LN Swanson, and LH Block. editors. Comprehensive pharmacy review. Philadelphia: Williams and Wilkins; (2001). p 289–291.
  • MR Griffin, A Yared, and WA Ray. (2000). Nonsteroidal Antiinflammatory Drugs and Acute Renal Failure in Elderly Persons. Am J Epidemiol 151:488–496.
  • G Singh, and G Triadafilopoulos. (1999). Epidemiology of NSAID induced gastrointestinal complications. J Rheumatol 26:18–24.
  • Y Song, DT Connor, R Doubleday, RJ Sorenson, AD Sercel, PC Unangst, BD Roth, RB Gilbertsen, K Chan, DJ Schrier, A Guglietta, DA Bornemeier, and RD Dyer. (1999). Synthesis, structure-activity relationships, and in vivo evaluations of substituted Di-tert-butylphenols as a novel class of potent, selective, and orally active Cyclooxygenase-2 inhibitors 1. Thiazolone and Oxazolone Series. J Med Chem 42:1151–1160.
  • NV Chandrasekharan, H Dai, KL Turepu Roos, NK Evanson, J Tomsik, TS Elton, and DL Simmons. (2002). COX-3, a cyclooxygenase-1 variant inhibited by acetaminophen and other analgesic/antipyretic drugs: Cloning, structure and expression. PNAS 99:13926–13931.
  • A Palomer, F Cabre, J Pascual, J Campos, MA Trujillo, A Entrena, MA Callo, L Garcia, D Mauleon, and A Espinosa. (2002). Identification of novel Cyclooxygenase-2 selective inhibitors using pharmacophore models. J Med Chem 45:1402–1411.
  • AK Gadad, BS Kittur, SG Kapsi, CS Mahajanshetti, and SB Rajur. (1996). Synthesis, analgesic and anti-inflammatory activities of some 1-acyl/aracyl-5-aminopyrazole derivatives. Arzneim Forsch 46:1082–1085.
  • TD Penning, JJ Talley, SR Bertenshaw, JS Carter, PW Collins, S Docter, MJ Graneto, LF Lee, JW Malecha, JM Miyashiro, RS Rogers, DJ Rogier, SS Yu, GD Anderson, EG Burton, JN Cogburn, SA Gregory, CM Koboldt, WE Perkins, K Seibert, AW Veenhuizen, YY Zhang, and PC Isakson. (1997). 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 40:1347–1365.
  • K Tsuji, K Nakamura, T Ogino, N Konishi, T Tojo, T Ochi, N Seki, and M Matsuo. (1998). Studies on anti-inflammatory agents. VI. Synthesis and pharmacological properties of 2,3-diarylthiophenes. Chem Pharm Bull 46:279–286.
  • SA Beers, EA Malloy, W Wu, M Wachter, J Ansell, M Singer, M Steber, A Barbone, T Kirchner, D Ritchie, and D Argentieri. (1997). N-(5-substituted) thiophene-2-alkylsulfonamides as potent inhibitors of 5-lipoxygenase. Bioorg Med Chem Lett 5:779–786.
  • DH Boschelli, DT Connor, DA Bornemeier, RD Dyer, JA Kennedy, PJ Kuipers, GC Okonkwo, DJ Schrier, and CD Wright. (1993). 1,3,4-oxadiazole 1,3,4-thiadiazole, and 1,2,4-triazole analogs of the fenamates: In vitro inhibition of cyclooxygenase and 5-lipoxygenase activities. J Med Chem 36:1802–1810.
  • A Tanitame, Y Oyamada, K Ofuji, Y Kyoya, K Suziki, H Ito, M Kawasaki, K Nagai, M Wachi, and J Yamagishi. (2004). Design, synthesis and structure-activity relationship studies of novel indazole analogues as DNA gyrase inhibitors with Gram-positive antibacterial activity. Bioorg Med Chem Lett 14:2857–2862.
  • A Tanitame, Y Oyamada, K Ofuji, K Suziki, H Ito, M Kawasaki, M Wachi, and J Yamagishi. (2004). Potent DNA gyrase inhibitors; novel 5-vinylpyrazoleanalogues with Gram-positive antibacterial activity. Bioorg Med Chem Lett 14:2863–2866.
  • A Tanitame, Y Oyamada, K Ofuji, M Fujimoto, N Iwai, Y Hiyama, K Suziki, H Ito, H Terauchi, M Kawasaki, K Nagai, M Wachi, and J Yamagishi. (2004). Design, synthesis and antibacterial activity of a novel series of potent DNA gyrase inhibitor. Pyrazole derivatives. J Med Chem 47:3693–3696.
  • AM Farghaly, AA Bekhit, and JY Park. (2000). Design and synthesis of some oxadiazolyl, thiadiazolyl, thiazolidinyl, and thiazolyl derivatives of 1H-pyrazole as anti-inflammatory antimicrobial agents. Arch Pharm Pharm Med Chem 333:53–57.
  • AA Bekhit, and T Abdel-Azeim. (2004). Design, synthesis and biological evaluation of some pyrazole derivatives as anti-inflammatory-antimicrobial agents. Bioorg Med Chem 12:1935–1945.
  • AA Bekhit, HTY Fahmy, ShAF Rostom, and AM Baraka. (2003). Design and synthesis of some substituted 1H-pyrazolyl-thiazolo[4,5-d]pyrimidines as anti-inflammatory-antimicrobial agents. Eur J Med Chem 38:27–36.
  • AA Bekhit, and HTY Fahmy. (2003). Design and synthesis of some substituted 1H-pyrazolyl-oxazolidines or 1H-pyrazolyl-thiazolidines as anti-inflammatory-antimicrobial agents. Arch Pharm Pharm Med Chem 336:111–118.
  • Bekhit AA. Egyptian Patent GATT/TRIPS Treaty, Appl. No. 1117 12 2003..
  • AA Bekhit, HMA Ashour, and A Guemei. (2005). Novel Pyrazole Derivatives as Potential Promising Anti-inflammatory Antimicrobial Agents. Arch Pharm Chem Life Sci 338:167–174.
  • AA Bekhit, HM Abdel-Rahman, and A Guemei. (2006). Synthesis and biological evaluation of some hydroxypyrazole derivatives as anti-inflammatory-antimicrobial agents. Arch Pharm Chem Life Sci 339:81–87.
  • R Meier, W Schuler, and P Desaulles. (1950). On the mechanism of cortisone inhibition of connective tissue proliferation. Experientia 6:469–471.
  • M Di Rosa, and DA Willoughby. (1971). Screens for anti-inflammatory drugs. J Pharm Pharmacol 23:297–298.
  • K Wakitani, T Nanayama, M Masaki, and M Matsushita. (1998). Profile of JTE-522 as a human cyclooxygenase-2 inhibitor. Jpn J Pharmacol 78:365–371.
  • S Hammarström, P Falardeau. Resolution of prostaglandin endoperoxide synthase and thromboxane synthase of human platelets PNAS 1977;74:3691–3695.
  • MS Abou Zeit-Har, T Verimer, and JP Long. (1982). Effect of long term estrogen and lithium treatment on restraint induced gastric erosion in intact and ovariectomized rats. Pharmazie 37:593–595.
  • M Verma, M Tripathi, AK Saxena, and K Shanker. (1994). Anti-inflammatory activity of novel indole derivatives. Eur J Med Chem 29:941–946.
  • JT Litchfield, and F Wilcoxon. (1949). A simplified method of evaluating dose-effect experiments. J Pharmacol Exp Ther 96:99–113.
  • Molecular Operating Environment (MOE). Montreal, Canada: Chemical Computing Group, Inc; http://www.chemcomp.com.
  • GL Woods, and AW. Washington. In: PR Murray, EJ Baron, MA Pfaller, FC Tenover, and RH Yolken. editors. Manual of Clinical Microbiology. Washington, D.C: Am Soc Microbiol; (1995).
  • M Bernard, E Hulley, H Molenda, K Stochla, and U Wrzeciono. (1986). Azole. XVII: β-(4-Pyrazol)acryl- bzw. -propionsäure und ihre antiphlogistische Wirkung. Pharmazie 41:560–562.
  • E Pretsch, P Bühlmann, and C Affolter. Structure Determination of Organic Compounds. Berlin Heidelberg New York: Springer-Verlag; (2000) p212.
  • AK Sen, and AK Mukhopadhyay. (1984). Synthesis of compounds related to 4(5)-aminoimidazole-5(4)-carboxamides: Part VI – synthesis of 3-(6-methoxy-8-quinolyl)-7-methylpurin-6(3H)-one. Indian J Chem Sect B 28B (9):870–873.
  • E Pretsch, P Bühlmann, and C Affolter. editors Structure Determination of Organic Compounds. Berlin Heidelberg New York: Springer-Verlag; (2000). p 211.
  • VD Piaz, MP Giovannoni, C Castellana, JM Palacios, J Beleta, T Domench, and V Segarra. (1998). Heterocyclic-fused 3(2H)-pyridazinones as potent and selective PDE IV inhibitors: Further structure-activity relationships and molecular modelling studies. Eur J Med Chem 33:789–797.
  • RG Kurumbail, AM Stevens, JK Gierse, JJ McDonald, RA Stegeman, JY Pak, D Gildehaus, JM Iyashiro, TD Penning, K Seibert, PC Isakson, and WC Stallings. (1996). Structural basis for selective inhibition of cyclooxygenase-2 by anti-inflammatory agents. Nature 384:644–648.

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