1,239
Views
15
CrossRef citations to date
0
Altmetric
Research Article

Synthesis of some new amide-linked bipyrazoles and their evaluation as anti-inflammatory and analgesic agents

, , , , , , & show all
Pages 1079-1094 | Received 09 Jun 2015, Accepted 05 Aug 2015, Published online: 20 Oct 2015

References

  • Nathan C. Points of control in inflammation. Nature 2002;420:846–52
  • Vane RJ, Botting RM. Mechanism of action of anti-inflammatory drugs. Scand J Rheumatol Suppl 1996;102:9–21
  • Meade EA, Smith WL, DeWitt DL. Differential inhibition of prostaglandin endoperoxide synthase (cyclooxygenase) isozymes by aspirin and other non-steroidal anti-inflammatory drugs. J Biol Chem 1993;268:6610–14
  • Vane JR, Botting RM. Anti-inflammatory drugs and their mechanism of action. Inflamm Res 1998;47:78–87
  • Qiu KM, Yan R, Xing M, et al. Synthesis, biological evaluation and molecular modeling of dihydro-pyrazolyl-thiazolinone derivatives as potential COX-2 inhibitors. Bioorg Med Chem 2012;20:6648–54
  • Feldmann M, Brennan FM, Maini RN. Role of cytokines in rheumatoid arthritis. Annu Rev Immunol 1996;14:397–440
  • Maini RN, Taylor PC. Anti-cytokine therapy for rheumatoid arthritis. Annu Rev Med 2000;51:207–29
  • Parente L, Perretti M. Advances in the pathophysiology of constitutive and inducible cyclooxygenases: two enzymes in the spotlight. Biochem Pharmacol 2003;65:153–9
  • Allison MC, Howatson AG, Torrance CJ, et al. Gastrointestinal damage associated with the use of nonsteroidal antiinflammatory drugs. N Engl J Med 1992;327:749–54
  • Hajjar ER, Cafiero AC, Hanlon JT. Polypharmacy in elderly patients. Am J Geriatr Pharmacother 2007;5:345–51
  • Burnier M. The safety of rofecoxib. Expert Opin Drug Saf 2005;4:491–9
  • Sharma PK, Kumar S, Kumar P, et al. Synthesis and biological evaluation of some pyrazolylpyrazolines as anti-inflammatory-antimicrobial agents. Eur J Med Chem 2010;45:2650–5
  • Jadhav SY, Shirame SP, Kulkarni SD, et al. PEG mediated synthesis and pharmacological evaluation of some fluoro substituted pyrazoline derivatives as antiinflammatory and analgesic agents. Bioorg Med Chem Lett 2013;23:2575–8
  • Youssef AM, White MS, Villanueva EB, et al. Synthesis and biological evaluation of novel pyrazolyl-2,4-thiazolidinediones as anti-inflammatory and neuroprotective agents. Bioorg Med Chem 2010;18:2019–28
  • Vijesh AM, Isloor AM, Shetty P, et al. New pyrazole derivatives containing 1,2,4-triazoles and benzoxazoles as potent antimicrobial and analgesic agents. Eur J Med Chem 2013;62:410–15
  • Ragab FA, Abdel Gawad NM, Georgey HH, et al. Synthesis of novel 1,3,4-trisubstituted pyrazoles as anti-inflammatory and analgesic agents. Eur J Med Chem 2013;63:645–54
  • Fioravanti R, Bolasco A, Manna F, et al. Synthesis and biological evaluation of N-substituted-3,5-diphenyl-2-pyrazoline derivatives as cyclooxygenase (COX-2) inhibitors. Eur J Med Chem 2010;45:6135–8
  • El-Sayed MA, Abdel-Aziz N, Abdel-Aziz I. AA, et al. Design, synthesis, and biological evaluation of substituted hydrazone and pyrazole derivatives as selective COX-2 inhibitors: molecular docking study. Bioorg Med Chem 2011;19:3416–24
  • Singh P, Mittal A. Current status of COX-2 inhibitors. Mini Rev Med Chem 2008;8:73–90
  • Ranatunge RR, Garvey DS, Janero DR, et al. Synthesis and selective cyclooxygenase-2 (COX-2) inhibitory activity of a series of novel bicyclic pyrazoles. Bioorg Med Chem 2004;12:1357–66
  • Bekhit AA, Hymete A, El-Din ABA, et al. Pyrazoles as promising scaffold for the synthesis of anti-inflammatory and/or antimicrobial agent: a review. Mini Rev Med Chem 2010;10:1014–33
  • Bandgar BP, Gawande SS, Bodade RG, et al. Synthesis and biological evaluation of a novel series of pyrazole chalcones as anti-inflammatory, antioxidant and antimicrobial agents. Bioorg Med Chem 2009;17:8168–73
  • Bekhit AA, Fahmy HT, Rostom SA, et al. Synthesis and biological evaluation of some thiazolylpyrazole derivatives as dual anti-inflammatory antimicrobial agents. Eur J Med Chem 2010;45:6027–38
  • Bekhit AA, Abdel-Aziem T. Design, synthesis and biological evaluation of some pyrazole derivatives as anti-inflammatory-antimicrobial agents. Bioorg Med Chem 2004;12:1935–45
  • Khalil NA, Ahmed EM, El-Nassan HB, et al. Synthesis and biological evaluation of novel pyrazoline derivatives as anti-inflammatory and antioxidant agents. Arch Pharm Res 2012;35:995–1002
  • Bandgar BP, Adsul LK, Chavan HV, et al. Synthesis, biological evaluation, and docking studies of 3-(substituted)-aryl-5-(9-methyl-3-carbazole)-1H-2-pyrazolines as potent anti-inflammatory and antioxidant agents. Bioorg Med Chem Lett 2012;22:5839–44
  • Bekhit AA, Ashour HMA, Guemei A. Novel pyrazole derivatives as potential promising anti-inflammatory antimicrobial agents. Arch Pharm (Weinheim) 2005;338:167–74
  • Bekhit AA, Ashour HM, Bekhit A-D, et al. Synthesis of some pyrazolyl benzenesulfonamide derivatives as dual anti-inflammatory antimicrobial agents. J Enzyme Inhib Med Chem 2009;24:296–309
  • Bekhit AA, Ashour HM, Abdel Ghany YS, et al. Synthesis and biological evaluation of some thiazolyl and thiadiazolyl derivatives of 1H-pyrazole as anti-inflammatory antimicrobial agents. Eur J Med Chem 2008;43:456–63
  • Bekhit AA, Ashour HM, Bekhit A-D, et al. Synthesis and biological evaluation of novel pyrazole derivatives as anti-inflammatory antimicrobial agents. Med Chem 2009;5:103–17
  • Rostom SA, el-Ashmawy IM, Abd el Razik HA, et al. Design and synthesis of some thiazolyl and thiadiazolyl derivatives of antipyrine as potential non-acidic anti-inflammatory, analgesic and antimicrobial agents. Bioorg Med Chem 2009;17:882–95
  • Tominaga Y, Honkawa Y, Hara M, et al. Synthesis of pyrazolo[3,4-d]pyrimidine derivatives using ketene dithioacetals. J Heterocycl Chem 1990;27:775–83
  • Claudino RF, Kassuya CA, Ferreira J, et al. Pharmacological and molecular characterization of the mechanisms involved in prostaglandin E2-induced mouse paw edema. J Pharmacol Exp Ther 2006;318:611–18
  • Abbas SE, Awadallah FM, Ibrahin NA, et al. New quinazolinone-pyrimidine hybrids: synthesis, anti-inflammatory, and ulcerogenicity studies. Eur J Med Chem 2012;53:141–9
  • Güvenç A, Küpeli Akkol E, Süntar I, et al. Biological activities of Pseudevernia furfuracea (L.) Zopf extracts and isolation of the active compounds. J Ethnopharmacol 2012;144:726–34
  • Lee SH, Son MJ, Ju HK, et al. Dual inhibition of cyclooxygenases-2 and 5-lipoxygenase by deoxypodophyllotoxin in mouse bone marrow-derived mast cells. Biol Pharm Bull 2004;27:786–8
  • Rodríguez RE, Rodríguez FD, Sacristán MP, et al. Antinociceptive activity of glycosidic enkephalin analogues. Psychopharmacology (Berl) 1990;101:222–5
  • Salaheldin AM. Cyanoacetylation of 5-Aminopyrazole: synthesis of 2-(1-Aryl-4-substituted pyrazolo[3,4-d]pyrimidin-6-yl)acetonitrile Derivatives. Z Naturforsch 2009;64b:840–6
  • Shams HZ, Mohareb RM, Helal MH, et al. Novel synthesis and antitumor evaluation of polyfunctionally substituted heterocyclic compounds derived from 2-cyano-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-acetamide. Molecules 2010;16:52–73
  • Fadda AA, Elattar KM. Synthesis of novel azo disperse dyes derived from 4-aminoantipyrine and their applications to polyester fabrics. Am J Org Chem 2012;2:52–7
  • Bernard M, Hulley E, Molenda H, et al. [Azoles. 17. Beta-(4-pyrazol)acrylic and propionic acids and their anti-inflammatory activity]. Pharmazie 1986;41:560–2
  • Ibrahim HM, Makhseed S, Abdel-Motaleb RM, et al. Utility of cyanoacetamides as precursors to pyrazolo[3,4-d]pyrimidine-4-ones, 2-aryl-6-substituted 1,2,3-triazolo[4,5-d]pyrimidines and pyrazolo[1,5-a]pyrimidine-3-carboxamides. Heterocycles 2007;71:1951–66
  • Behbehani H, Ibrahim HM, Makhseed S, et al. 2-Aminothiophenes as building blocks in heterocyclic synthesis: synthesis and antimicrobial evaluation of a new class of pyrido[1,2-a]thieno[3,2-e]pyrimidine, quinoline and pyridin-2-one derivatives. Eur J Med Chem 2012;52:51–65
  • Gouda MA, Berghot MA, Shoeib AI, et al. Synthesis and antimicrobial of new anthraquinone derivatives incorporating pyrazole moiety. Eur J Med Chem 2010;45:1843–8
  • Elgemeie GH, Widyan K, Kurz T. Novel synthesis of fluorinated cyanoketene N,S acetals and their conversions to fluorinated pyrazole derivatives. Phosphorus Sulfur Silicon 2006;181:299–304
  • Frisch MJ, Trucks W, Schlegel GHB, et al. Gaussian 09, Revision B.01. Wallingford, CT: Gaussian, Inc.; 2010
  • Ammar YA, El-Sharief AMS, Al-Sehemi AG, et al. Cyanoacetanilides intermediates in heterocyclic synthesis. Part 2: preparation of some hitherto unknown ketene dithioacetal, benzoazole and pyridone derivatives. J Chinese Chem Soc 2005;52:553–8
  • Goodwin DC, Landino LM, Marnett LJ. Effects of nitric oxide and nitric oxide-derived species on prostaglandin endoperoxide synthase and prostaglandin biosynthesis. FASEB J 1999;13:1121–36
  • Kim SF, Huri DA, Snyder SH. Inducible nitric oxide synthase binds, S-nitrosylates, and activates cyclooxygenase-2. Science 2005;310:1966–70
  • Mollace V, Muscoli C, Masini E, et al. Modulation of prostaglandin biosynthesis by nitric oxide and nitric oxide donors. Pharmacol Rev 2005;57:217–52
  • Vassalle C, Domenici C, Lubrano V, et al. Interaction between nitric oxide and cyclooxygenase pathways in endothelial cells. J Vasc Res 2003;40:491–9
  • Sibilia V, Pagani F, Rindi G, et al. Central ghrelin gastroprotection involves nitric oxide/prostaglandin cross-talk. Br J Pharmacol 2008;154:688–97

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.