Design, synthesis, molecular modelling and biological evaluation of novel 3-(2-naphthyl)-1-phenyl-1H-pyrazole derivatives as potent antioxidants and 15-Lipoxygenase inhibitors

References

• Lobo V, Patil A, Phatak A, Chandra N. Free radicals, antioxidants and functional foods: impact on human health. Pharm Rev 2010;4:118–26.
   PubMedGoogle Scholar
• Lu JM, Lin PH, Yao Q, Chen C. Chemical and molecular mechanisms of antioxidants: experimental approaches and model systems. J Cellular Mol Med 2010;14:840–60.
   PubMed Web of Science ®Google Scholar
• Singh PP, Chandra A, Mahdi F, et al. Reconvene and reconnect the antioxidant hypothesis in human health and disease. Indian J Clin Biochem 2010;25:225–43.
   PubMedGoogle Scholar
• Wiernsperger NF. Oxidative stress as a therapeutic target in diabetes: revisiting the controversy. Diabet Metabol 2003;29:579–85.
   PubMed Web of Science ®Google Scholar
• Valko M, Izakovic M, Mazur M, et al. Role of oxygen radicals in DNA damage and cancer incidence. Mol Cellular Biochem 2004;266:37–56.
   PubMed Web of Science ®Google Scholar
• Craft BD, Kerrihard AL, Amarowicz R, Pegg RB. phenol-based antioxidants and the in vitro methods used for their assessment. Comprehensive Rev Food Sci Food Safety 2012;11:148–73.
   Web of Science ®Google Scholar
• Rahman K. Studies on free radicals, antioxidants, and co-factors. Clin Intervent Aging 2007;2:219–36.
   PubMed Web of Science ®Google Scholar
• Halliwell B. Biochemistry of oxidative stress. Biochem Soc Trans 2007;35:1147–50.
   PubMed Web of Science ®Google Scholar
• Akhtar MJ, Khan AA, Ali Z, et al. Synthesis of stable benzimidazole derivatives bearing pyrazole as anticancer and EGFR receptor inhibitors. Bioorgan Chem 2018;78:158–69.
   PubMed Web of Science ®Google Scholar
• Farghaly TA, Abdel Hafez NA, Ragab EA, et al. Synthesis, anti-HCV, antioxidant, and peroxynitrite inhibitory activity of fused benzosuberone derivatives. Eur J Med Chem 2010;45:492–500.
   PubMed Web of Science ®Google Scholar
• Maurya HK, Verma R, Alam S, et al. Studies on substituted benzo[h]quinazolines, benzo[g]indazoles, pyrazoles, 2,6-diarylpyridines as anti-tubercular agents. Bioorgan Med Chem Lett 2013;23:5844–9.
   PubMed Web of Science ®Google Scholar
• Sayed GH, Azab ME, Anwer KE, et al. Pyrazole, pyrazolone and enaminonitrile pyrazole derivatives: Synthesis, characterization and potential in corrosion inhibition and antimicrobial applications. J Mol Liquids 2018;252:329–38.
   Web of Science ®Google Scholar
• Bekhit AA, Hassan AM, Abd El Razik HA, et al. New heterocyclic hybrids of pyrazole and its bioisosteres: design, synthesis and biological evaluation as dual acting antimalarial-antileishmanial agents. Eur J Med Chem 2015;94:30–44.
   PubMed Web of Science ®Google Scholar
• Taher AT, Mostafa Sarg MT, El-Sayed Ali NR, Hilmy Elnagdi N. Hilmy Elnagdi N. Design, synthesis, modeling studies and biological screening of novel pyrazole derivatives as potential analgesic and anti-inflammatory agents. Bioorgan Chem 2019;89:103023.
   PubMed Web of Science ®Google Scholar
• Hasui T, Ohyabu N, Ohra T. Discovery of 6-[5-(4-fluorophenyl)-3-methyl-pyrazol-4-yl]-benzoxazin-3-one derivatives as novel selective nonsteroidal mineralocorticoid receptor antagonists. Bioorgan Med Chem 2014;22:5428–45.
   PubMed Web of Science ®Google Scholar
• Xu Y, Zhang Z, Jiang X, et al. Discovery of delta-sultone-fused pyrazoles for treating Alzheimer’s disease: design, synthesis, biological evaluation and SAR studies. Eur J Med Chem 2019;181:111598.
   PubMed Web of Science ®Google Scholar
• Hoveyda HR, Roy MO, Blanc S, et al. Discovery of 3-aryl-5-acylpiperazinyl-pyrazoles as antagonists to the NK3 receptor. Bioorgan Med Chem Lett 2011;21:1991–6.
   PubMed Web of Science ®Google Scholar
• Jimenez HN, Liu KG, Hong SP, et al. 4-(1-Phenyl-1H-pyrazol-4-yl)quinolines as novel, selective and brain penetrant metabotropic glutamate receptor 4 positive allosteric modulators. Bioorgan Med Chem Lett 2012;22:3235–9.
   PubMed Web of Science ®Google Scholar
• Hassan GS, Abou-Seri SM, Kamel G, Ali MM. Celecoxib analogs bearing benzofuran moiety as cyclooxygenase-2 inhibitors: design, synthesis and evaluation as potential anti-inflammatory agents. Eur J Med Chem 2014;76:482–93.
   PubMed Web of Science ®Google Scholar
• Sun HY, Ji FQ. A molecular dynamics investigation on the crizotinib resistance mechanism of C1156Y mutation in ALK. Biochem Biophys Res Commun 2012;423:319–24.
   PubMed Web of Science ®Google Scholar
• Tripodi A, Padovan L, Veena C, et al. How the direct oral anticoagulant apixaban affects thrombin generation parameters. Thrombosis Res 2015;135:1186–90.
   PubMed Web of Science ®Google Scholar
• Wyde PR, Gilbert BE, Ambrose MW. Comparison of the anti-respiratory syncytial virus activity and toxicity of papaverine hydrochloride and pyrazofurin in vitro and in vivo. Antiviral Res 1989;11:15–26.
   PubMed Web of Science ®Google Scholar
• Luttinger DHD. Antidepressant agents. Annu Rep Med Chem 1987; 22:21–30.
   Web of Science ®Google Scholar
• Prabhu VV, Kannan N, Guruvayoorappan C. 1,2-Diazole prevents cisplatin-induced nephrotoxicity in experimental rats. Pharmacol Rep 2013;65:980–90.
   PubMed Web of Science ®Google Scholar
• Watanabe T, Egawa M. Effects of an antistroke agent MCl-186 on cerebral arachidonate cascade. J Pharmacol Exp Ther 1994;271:1624–9.
   PubMed Web of Science ®Google Scholar
• Watanabe T, Yuki S, Egawa M, Nishi H. Protective effects of MCI-186 on cerebral ischemia: possible involvement of free radical scavenging and antioxidant actions. J Pharmacol Exp Ther 1994;268:1597–604.
   PubMed Web of Science ®Google Scholar
• Okatani Y, Wakatsuki A, Enzan H, Miyahara Y. Edaravone protects against ischemia/reperfusion-induced oxidative damage to mitochondria in rat liver. Eur J Pharmacol 2003;465:163–70.
   PubMed Web of Science ®Google Scholar
• Sribalan R, Banuppriya G, Kirubavathi M, et al. Multiple biological activities and molecular docking studies of newly synthesized 3-(pyridin-4-yl)-1H-pyrazole-5-carboxamide chalcone hybrids. Bioorgan Med Chem Lett 2016;26:5624–30.
   PubMed Web of Science ®Google Scholar
• Achutha D, Hamse V, Ningappa M, et al. Synthesis and in vitro biological evaluation for antioxidant, anti-inflammatory activities and molecular docking studies of novel pyrazole derivatives. Biointer Res Appl Chem 2017;7:2040–7.
   Web of Science ®Google Scholar
• Samshuddin S, Narayana B, Sarojini BK, et al. Synthesis, characterization and biological evaluation of some pyrazoles derived from α, β-dibromo 4, 4’-difluoro chalcone. Der Pharm Chem 2012;4:587–92.
   Google Scholar
• Adhikari A, Kalluraya B, Sujith KV, et al. Synthesis, characterization and pharmacological study of 4,5-dihydropyrazolines carrying pyrimidine moiety. Eur J Med Chem 2012;55:467–74.
   PubMed Web of Science ®Google Scholar
• Faidallah HM, Rostom SA, Khan KA. Synthesis and biological evaluation of pyrazole chalcones and derived bipyrazoles as anti-inflammatory and antioxidant agents. Arch Pharm Res 2015;38:203–15.
   PubMed Web of Science ®Google Scholar
• Mallikarjuna Reddy G, Muralikrishna A, Padmavathi V, et al. Synthesis and antioxidant activity of styrylsulfonylmethyl 1,3,4-oxadiazoles, pyrazolyl/isoxazolyl-1,3,4-oxadiazoles. Chem Pharm Bull 2013;61:1291–7.
   PubMed Web of Science ®Google Scholar
• Ningaiah S, Bhadraiah UK, Keshavamurthy S, Javarasetty C. Novel pyrazoline amidoxime and their 1,2,4-oxadiazole analogues: synthesis and pharmacological screening. Bioorgan Med Chem Lett 2013;23:4532–9.
   PubMed Web of Science ®Google Scholar
• Hamada NM, Abdo NY. Synthesis, characterization, antimicrobial screening and free-radical scavenging activity of some novel substituted pyrazoles. Molecules 2015;20:10468–86.
   PubMed Web of Science ®Google Scholar
• Heim KE, Tagliaferro AR, Bobilya DJ. Flavonoid antioxidants: chemistry, metabolism and structure-activity relationships. J Nutr Biochem 2002;13:572–84.
   PubMed Web of Science ®Google Scholar
• Pokorný J. Are natural antioxidants better – and safer – than synthetic antioxidants?. Eur J Lipid Sci Technol 2007;109:883.
   Web of Science ®Google Scholar
• Brash AR. Lipoxygenases: occurrence, functions, catalysis, and acquisition of substrate. J Biol Chem 1999;274:23679–23682.
   PubMed Web of Science ®Google Scholar
• Pontiki E, Hadjipavlou-Litina D. Lipoxygenases (LOs): an heterogenous family of lipid peroxidizing enzymes implicated in cell differentiation, inflammation, asthma, carcinogenesis, atherogenesis-an interesting target for the development of promising drugs. Curr Enzyme Inhibit 2005;1:309–327.
   Google Scholar
• Feltenmark S, Gautam N, Brunnstrom A, et al. Eoxins are proinflammatory arachidonic acid metabolites produced via the 15-lipoxygenase-1 pathway in human eosinophils and mast cells. Proc Natl Acad Sci USA 2008;105:680–685.
   PubMed Web of Science ®Google Scholar
• Kelavkar U, Lin Y, Landsittel D, et al. The yin and yang of 15-lipoxygenase-1 and delta-desaturases: dietary omega-6 linoleic acid metabolic pathway in prostate. J Carcinogenesis 2006;5:9.
   Google Scholar
• Bocan TMA, Rosebury WS, Mueller SB, et al. A specific 15-lipoxygenase inhibitor limits the progression and monocyte-macrophage enrichment of hypercholesterolemia-induced atherosclerosis in the rabbit. Atherosclerosis 1998;136:203–216.
   PubMed Web of Science ®Google Scholar
• Pratico D, Zhukareva V, Yao Y, et al. 12/15-lipoxygenase is increased in Alzheimer’s disease: possible involvement in brain oxidative stress. Am J Pathol 2004;164:1655–1662.
   PubMed Web of Science ®Google Scholar
• Ngu K, Weinstein DS, Liu W, et al. Pyrazole-based sulfonamide and sulfamides as potent inhibitors of mammalian 15-lipoxygenase. Bioorgan Med Chem Lett 2011;21:4141–4145.
   PubMed Web of Science ®Google Scholar
• Rai G, Joshi N, Jung JE, et al. Potent and selective inhibitors of human reticulocyte 12/15-lipoxygenase as anti-stroke therapies. J Med Chem 2014;57:4035–4048.
   PubMed Web of Science ®Google Scholar
• Arbačiauskienė E, Martynaitis V, Krikštolaitytė S, et al. Synthesis of 3-substituted 1-phenyl-1H-pyrazole-4-carbaldehydes and the corresponding ethanones by Pd-catalysed cross-coupling reactions. Arkivoc 2011;11:1–21.
   Web of Science ®Google Scholar
• Vovk MV, Mel'nichenko NV, Chornous VA, Bratenko MK. Intramolecular cyclization of 4-isocyanato-3-(2-naphthyl)-1-phenylpyrazole under Friedel-crafts reaction conditions. Chem Heterocyc Comp 2002;38:1096–1097.
   Google Scholar
• Nahar L, Russell WR, Middleton M, et al. Antioxidant phenylacetic acid derivatives from the seeds of Ilex aquifolium. Acta Pharm 2005;55:187–193.
   PubMedGoogle Scholar
• Padmaja A, Rajasekhar C, Muralikrishna A, Padmavathi V. Synthesis and antioxidant activity of oxazolyl/thiazolylsulfonylmethyl pyrazoles and isoxazoles. Eur J Med Chem 2011;46:5034–5038.
   PubMed Web of Science ®Google Scholar
• Ho S-C, Tang Y-L, Lin S-M, Liew Y-F. Evaluation of peroxynitrite-scavenging capacities of several commonly used fresh spices. Food Chem 2010;119:1102–1107.
   Web of Science ®Google Scholar
• Li X. Improved pyrogallol autoxidation method: a reliable and cheap superoxide-scavenging assay suitable for all antioxidants. J Agric Food Chem 2012;60:6418–6424.
   PubMed Web of Science ®Google Scholar
• OECD, Test No. 425; Acute Oral Toxicity:Up- and Down-Procedure, OECD Guidelines for the Testing of Chemicals, Section 4, Paris: OECD Publishing, 2008. http://doi.org/10.1787/9789264071049-en
   Google Scholar
• Alam MN, Bristi NJ, Rafiquzzaman M. Review on in vivo and in vitro methods evaluation of antioxidant activity. Saudi Pharm J 2013;21:143–152.
   PubMed Web of Science ®Google Scholar
• Sinha AK. Colorimetric assay of catalase. Anal Biochem 1972;47:389–394.
   PubMed Web of Science ®Google Scholar
• Beutler E, Duron O, Kelly BM. Improved method for the determination of blood glutathione. J Labor Clin Med 1963;61:882–888.
   PubMed Web of Science ®Google Scholar
• Mihara M, Uchiyama M. Determination of malonaldehyde precursor in tissues by thiobarbituric acid test. Anal Biochem 1978;86:271–278.
   PubMed Web of Science ®Google Scholar
• Awad SM, Zohny YM, Ali SA, Mahgoub S, et al. Design, synthesis, molecular modeling, and biological evaluation of novel thiouracil derivatives as potential antithyroid agents. Molecules 2018;23:2913.
   Web of Science ®Google Scholar
• Kucerova-Chlupacova M, Dosedel M, Kunes J, et al. Chalcones and their pyrazine analogs: synthesis, inhibition of aldose reductase, antioxidant activity, and molecular docking study. Monat Für Chem 2018;149:921–929.
   Web of Science ®Google Scholar
• Ahmed NM, Youns M, Soltan MK, Said AM. Design, synthesis, molecular modelling, and biological evaluation of novel substituted pyrimidine derivatives as potential anticancer agents for hepatocellular carcinoma. J Enzyme Inhibit Med Chem 2019;34:1110–1120.
   PubMed Web of Science ®Google Scholar
• Abd-Rabou AA, Abdel-Wahab BF, Bekheit MS. Synthesis, molecular docking, and evaluation of novel bivalent pyrazolinyl-1,2,3-triazoles as potential VEGFR TK inhibitors and anti-cancer agents. Chem Papers 2018;72:2225–2237.
   Web of Science ®Google Scholar
• Wei Q, Ning J-Y, Dai X, et al. Discovery of novel HSP90 inhibitors that induced apoptosis and impaired autophagic flux in A549 lung cancer cells. Eur J Med Chem 2018;145:551–558.
   PubMed Web of Science ®Google Scholar
• El-Desoky EI, Keshk EM, El-Sawi AA, et al. Synthesis, biological evaluation and in silico molecular docking of novel 1-hydroxy-naphthyl substituted heterocycles. Saudi Pharmaceutical J 2018;26:852–859.
   PubMed Web of Science ®Google Scholar
• Saueressig S, Tessmann J, Mastelari R, et al. Synergistic effect of pyrazoles derivatives and doxorubicin in claudin-low breast cancer subtype. Biomed Pharmacother 2018;98:390–398.
   PubMed Web of Science ®Google Scholar
• Muller K. 5-Lipoxygenase and 12-lipoxygenase: attractive targets for the development of novel antipsoriatic drugs. Arch Der Pharm 1994;327:3–19.
   PubMed Web of Science ®Google Scholar
• Kontogiorgis C, Litinas KE, Makri A, et al. Synthesis and biological evaluation of novel angular fused pyrrolocoumarins. J Enzyme Inhibit Med Chem 2008;23:43–49.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• Lobo PL, Poojary B, Kumsi M, et al. Synthesis, antimicrobial and antioxidant activities of 2-[1-{3,5-diaryl-4,5-dihydro-1H-pyrazolenyl}]-4-(4-nitrophenyl)-[1,3]-thiazoles. Med Chem Res 2013;22:1689–1699.
   Web of Science ®Google Scholar
• Lavanya G, Prakash TB, Sravya G, et al. Synthesis and antioxidant activity of bis unsaturated sulfones, bis pyrroles, and bis pyrazoles. Res Chem Interm 2015;41:8815–8828.
   Web of Science ®Google Scholar
• Kumar S, Kumar D, Manjusha Saroha K, et al. Antioxidant and free radical scavenging potential of Citrullus colocynthis (L.) Schrad. methanolic fruit extract. Acta Pharm 2008;58:215–220.
   PubMed Web of Science ®Google Scholar
• McCord JM. The evolution of free radicals and oxidative stress. Am J Med 2000;108:652–659.
   PubMed Web of Science ®Google Scholar
• Hochstein P, Atallah AS. The nature of oxidants and antioxidant systems in the inhibition of mutation and cancer. Mut Res 1988;202:363–375.
   PubMed Web of Science ®Google Scholar
• Yu BP, Yang R. Critical evaluation of the free radical theory of aging. A proposal for the oxidative stress hypothesis. Ann New York Acad Sci 1996;786:1–11.
   PubMed Web of Science ®Google Scholar
• Wu G, Fang YZ, Yang S, et al. Glutathione metabolism and its implications for health. J Nutr 2004;134:489–492.
   PubMed Web of Science ®Google Scholar
• Teixeira HD, Schumacher RI, Meneghini R. Lower intracellular hydrogen peroxide levels in cells overexpressing CuZn-superoxide dismutase. Proc Natl Acad Sci U.S.A. 1998;95:7872–7875.
   PubMed Web of Science ®Google Scholar
• Kobe MJ, Neau DB, Mitchell CE, et al. The structure of human 15-lipoxygenase-2 with a substrate mimic. The J Biol Chem 2014;289:8562–8569.
   PubMed Web of Science ®Google Scholar