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Research Article

Structure-based design, synthesis, molecular docking study and biological evaluation of 1,2,4-triazine derivatives acting as COX/15-LOX inhibitors with anti-oxidant activities

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Pages 1602-1611 | Received 25 Dec 2015, Accepted 15 Feb 2016, Published online: 30 Mar 2016

References

  • Khanapure SP, Garvey DS, Janero DR, et al. Eicosanoids in inflammation: biosynthesis, pharmacology, and therapeutic frontiers. Curr Top Med Chem 2007;7:311–40
  • Samuelsson B. The discovery of the leukotrienes. Am J Respir Crit Care Med 2000;161:S2–6
  • Pairet M, Engelhardt G. Distinct isoforms (COX‐1 and COX‐2) of cyclooxygenase: possible physiological and therapeutic implications. Fundam Clin Pharmacol 1996;10:1–15
  • Simmons DL, Xie W, Chipman JG, et al. Multiple cyclooxygenases: cloning of a mitogen-inducible form. In: Bailey JM, ed. Prostaglandins, leukotrienes, lipoxins, and PAF. Springer US; 1991:67–78
  • Fosslien E. Adverse effects of nonsteroidal anti-inflammatory drugs on the gastrointestinal system. Ann Clin Lab Sci 1998;28:67–81
  • McGettigan P, Henry D. Cardiovascular risk and inhibition of cyclooxygenase: a systematic review of the observational studies of selective and nonselective inhibitors of cyclooxygenase 2. JAMA 2006;296:1633–44
  • Khoshneviszadeh M, Ghahremani MH, Foroumadi A, et al. Design, synthesis and biological evaluation of novel anti-cytokine 1,2,4-triazine derivatives. Bioorg Med Chem 2013;21:6708–17
  • Cignarella G, Vianello P, Berti F, et al. Synthesis and pharmacological evaluation of derivatives structurally related to nimesulide. Eur J Med Chem 1996;31:359–64
  • Jang M, Cai L, Udeani GO, et al. Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science 1997;275:218–20
  • Bhardwaj A, Kaur J, Sharma SK, et al. Hybrid fluorescent conjugates of COX-2 inhibitors: search for a COX-2 isozyme imaging cancer biomarker. Bioorg Med Chem Lett 2013;23:163–8
  • Jiang B, Huang X, Yao H, et al. Discovery of potential anti-inflammatory drugs: diaryl-1,2,4-triazoles bearing N-hydroxyurea moiety as dual inhibitors of cyclooxygenase-2 and 5-lipoxygenase. Org Biomol Chem 2014;12:2114–27
  • Navidpour L, Shadnia H, Shafaroodi H, et al. Design, synthesis, and biological evaluation of substituted 2-alkylthio-1,5-diarylimidazoles as selective COX-2 inhibitors. Bioorg Med Chem 2007;15:1976–82
  • Qiu K-M, 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
  • Ghodsi R, Zarghi A, Daraei B, et al. Design, synthesis and biological evaluation of new 2,3-diarylquinoline derivatives as selective cyclooxygenase-2 inhibitors. Bioorg Med Chem 2010;18:1029–33
  • Reddy M, Billa VK, Pallela VR, et al. Design, synthesis, and biological evaluation of 1-(4-sulfamylphenyl)-3-trifluoromethyl-5-indolyl pyrazolines as cyclooxygenase-2 (COX-2) and lipoxygenase (LOX) inhibitors. Bioorg Med Chem 2008;16:3907–16
  • Sharma B, Singh P, Pilania P, et al. QSAR of 2-(4-methylsulphonylphenyl) pyrimidine derivatives as cyclooxygenase-2 inhibitors: simple structural fragments as potential modulators of activity. J Enzyme Inhibit Med Chem 2012;27:249–60
  • Irannejad H, Kebriaieezadeh A, Zarghi A, et al. Synthesis, docking simulation, biological evaluations and 3D-QSAR study of 5-aryl-6-(4-methylsulfonyl)-3-(metylthio)-1, 2, 4-triazine as selective cyclooxygenase-2 inhibitors. Bioorg Med Chem 2014;22:865–73
  • Dadashpour S, Tuylu Kucukkilinc T, Unsal Tan O, et al. Design, synthesis and in vitro study of 5,6‐diaryl‐1,2,4‐triazine‐3‐ylthioacetate derivatives as COX‐2 and β‐amyloid aggregation inhibitors. Archiv Pharm 2015;348:179–87
  • Shivarama Holla B, Gonsalves R, Sooryanarayana Rao B, et al. Synthesis of some new biologically active bis-(thiadiazolotriazines) and bis-(thiadiazolotriazinyl) alkanes. Il Farmaco 2001;56:899–903
  • Abdel-Rahman RM, Morsy J, Hanafy F, et al. Synthesis of heterobicyclic nitrogen systems bearing the 1,2,4-triazine moiety as anti-HIV and anticancer drugs: Part I. Die Pharm 1999;54:347–51
  • Congreve M, Andrews SP, Doré AS, et al. Discovery of 1,2,4-triazine derivatives as adenosine A(2A) antagonists using structure based drug design. J Med Chem 2012;55:1898–903
  • Hunt JT, Mitt T, Borzilleri R, et al. Discovery of the pyrrolo [2, 1-f][1, 2, 4] triazine nucleus as a new kinase inhibitor template. J Med Chem 2004;47:4054–9
  • Walters T, Aur R, Hernandez K, et al. 6-Azauridine in combination chemotherapy of childhood acute myelocytic leukemia. Cancer 1972;29:1057–60
  • Mullick P, Khan SA, Begum T, et al. Synthesis of 1,2,4-triazine derivatives as potential anti-anxiety and anti-inflammatory agents. Acta Pol Pharm Drug Res 2009;66:379–85
  • Portevin B, Tordjman C, Pastoureau P, et al. 1,3-Diaryl-4,5,6,7-tetrahydro-2 H-isoindole derivatives: a new series of potent and selective COX-2 inhibitors in which a sulfonyl group is not a structural requisite. J Med Chem 2000;43:4582
  • Black W, Bayly C, Belley M, et al. From indomethacin to a selective COX-2 inhibitor: development of indolalkanoic acids as potent and selective cyclooxygenase-2 inhibitors. Bioorg Med Chem Lett 1996;6:725–30
  • Leblanc Y, Black W, Chan C, et al. Synthesis and biological evaluation of both enantiomers of L-761,000 as inhibitors of cyclooxygenase 1 and 2. Bioorg Med Chem Lett 1996;6:731–6
  • Niedballa U, Bottcher I. eds. US Patent 4,440,776, 1984. Chem Abstr; 1980
  • Zykova TA, Zhu F, Zhai X, et al. Resveratrol directly targets COX-2 to inhibit carcinogenesis. Mol Carcinogen 2008;47:797–805
  • Lin S-J, Tsai W-J, Chiou W-F, et al. Selective COX-2 inhibitors. Part 2: Synthesis and biological evaluation of 4-benzylideneamino- and 4-phenyliminomethyl-benzenesulfonamides. Bioorg Med Chem 2008;16:2697–706
  • Almasirad A, Hosseini R, Jalalizadeh H, et al. Synthesis and analgesic activity of 2-phenoxybenzoic acid and N-phenylanthranilic acid hydrazides. Biol Pharm Bull 2006;29:1180–5
  • Patrignani P, Panara MR, Greco A, et al. Biochemical and pharmacological characterization of the cyclooxygenase activity of human blood prostaglandin endoperoxide synthases. J Pharmacol Exp Ther 1994;271:1705–12
  • Benzie IF, Strain J. Ferric reducing/antioxidant power assay: direct measure of total antioxidant activity of biological fluids and modified version for simultaneous measurement of total antioxidant power and ascorbic acid concentration. Methods Enzymol 1999;299:15–27
  • Sidhu RS, Lee JY, Yuan C, et al. Comparison of cyclooxygenase-1 crystal structures: cross-talk between monomers comprising cyclooxygenase-1 homodimers. Biochemistry 2010;49:7069–79
  • Kurumbail RG, Stevens AM, Gierse JK, et al. Structural basis for selective inhibition of cyclooxygenase-2 by anti-inflammatory agents. Nature 1996;384:644–8
  • Baytas S, Turan Dural N, Ozkan Y, et al. Synthesis, anti-inflammatory, antiplatelet and in silico evaluations of (E)-3-(3-(2, 3-dihydro-3-methyl-2-oxo-3H-benzoxazole-6-yl)-1-phenyl-1H-pyrazole-4-yl) acrylamides. Turk J Chem 2012;36:367–82
  • Malterud KE, Rydland KM. Inhibitors of 15-lipoxygenase from orange peel. J Agric Food Chem 2000;48:5576–80

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