Synthesis, in silico analysis and antidepressant activity of 1,3,4-oxadiazole derivatives
DOI:
https://doi.org/10.3329/bjp.v17i1.58728Keywords:
Antidepressant, 1,3,4-Oxadiazole1,3,4-oxadiazoleAbstract
The compounds 1,3,4-oxadiazole derivatives (1-8) were synthesized by the cyclization of 4-hydroxy benzhydrazide (1) with various substituted aroma-tic aldehydes (2) using FeCl3 as catalyst and methanol as a solvent medium. The structures of the newly synthesized compounds were assigned based on FT-IR, 1H-NMR, and mass spectral data. In vivo antidepressant activity was performed by tail suspension test and forced swimming test models. Using the Schrodinger Maestro, the in silico analysis was performed and docked to the glycogen synthase kinase 3β binding site (PDB: 3GB2). Compounds 8 [4,4'-(1,3,4-oxadiazole-2,5-diyl)diphenol] and 3 [3-(5-(4-hydroxyphenyl)-1,3,4-oxadiazol-2-yl) phenol] showed both potent inhibitory activity against GSK-3β with a docking score of -7.800 kcal/mol as well as good antidepressant activity in both tail suspension and forced swimming tests models. The synthesized derivatives showed good antidepressive potential.
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Aboraia AS, Abdel-Rahman HM, Mahfouz NM, El-Gendy MA. Novel 5-(2-hydroxyphenyl)-3-substituted-2, 3-dihydro-1, 3, 4-oxadiazole-2-thione derivatives: Promising anticancer agents. Bioorg Med Chem. 2006; 14: 1236-46.
Arshad M. 1, 3, 4-oxadiazole nucleus with versatile pharmacological applications: A review. Int J Pharm Sci Res. 2014; 5: 1124-37.
Aslam M. Tail suspension test to evaluate the antidepressant activity of experimental drugs. Bangladesh J Pharmacol. 2016; 11: 292-94.
Beurel E, Grieco SF, Jope RS. Glycogen synthase kinase-3 (GSK3): Regulation, actions, and diseases. Pharmacol Ther. 2015; 148: 114-31.
Bhandari SV, Bothara KG, Raut MK, Patil AA, Sarkate AP, Mokale VJ. Design, synthesis and evaluation of anti-inflammatory, analgesic and ulcerogenicity studies of novel S-substituted phenacyl-1, 3, 4-oxadiazole-2-thiol and Schiff bases of diclofenac acid as nonulcerogenic derivatives. Bioorg Med Chem. 2008; 16: 1822-31.
Can A, Dao DT, Arad M, Terrillion CE, Piantadosi SC, Gould TD. The mouse forced swim test. JoVE. 2012; 29: e3638.
Casey DE. Metabolic issues and cardiovascular disease in patients with psychiatric disorders. Am J Med (Suppl). 2005; 118: 15-22.
Chemicals DO. OECD Guideline for testing of chemicals. The Organization for Economic Co-operation and Development. Paris, 2005, pp 1-3.
Chen CJ, Song BA, Yang S, Xu GF, Bhadury PS, Jin LH, Hu DY, Li QZ, Liu F, Xue W, Lu P. Synthesis and antifungal activities of 5-(3, 4, 5-trimethoxyphenyl)-2-sulfonyl-1, 3, 4-thiadiazole and 5-(3, 4, 5-trimethoxyphenyl)-2-sulfonyl-1, 3, 4-oxadiazole derivatives. Bio-org Med Chem. 2007; 15: 3981-89.
Desai NC, Kotadiya GM, Trivedi AR, Khedkar VM, Jha PC. Design, synthesis, and biological evaluation of novel fluorinated pyrazole encompassing pyridyl 1, 3, 4-oxadiazole motifs. Med Chem Res. 2016; 25: 2698-17.
Duda P, Hajka D, Wójcicka O, Rakus D, Gizak A. GSK3β: A Master player in depressive disorder pathogenesis and treatment responsiveness. Cells 2020; 9: 727-40.
Haq IU, Aslam M, Ahmed H, Sultana N. Antidepressant-like activity of hydroalcoholic extract of Agaricus blazei in stressed and unstressed mice. Bangladesh J Pharmacol. 2019; 14: 136-43.
Karege F, Perroud N, Burkhardt S, Fernandez R, Ballmann E, La Harpe R, Malafosse A. Protein levels of beta-catenin and activation state of glycogen synthase kinase-3beta in major depression: A study with post-mortem prefrontal cortex. J Affect Disord. 2012; 136: 185-88
Kramer T, Schmidt B, Lo Monte F. Small-molecule inhibitors of GSK-3: Structural insights and their application to Alzhei-mer's disease models. Int J Alzheimer’s Dis. 2012; 2012.
Li X, Zhu W, Roh MS, Friedman AB, Rosborough K, Jope RS. In vivo regulation of glycogen synthase kinase-3 β (GSK3 β) by serotonergic activity in mouse brain. Neuropsychopharmacology 2004; 29: 1426-31.
Lou JS, Reeves A, Benice T, Sexton G. Fatigue, and depression are associated with poor quality of life in ALS. Neurology 2003; 60: 122-33.
Macaev F, Ribkovskaia Z, Pogrebnoi S, Boldescu V, Rusu G, Shvets N, Dimoglo A, Geronikaki A, Reynolds R. The structure–antituberculosis activity relationships study in a series of 5-aryl-2-thio-1, 3, 4-oxadiazole derivatives. Bioorg Med Chem. 2011; 19: 6792-807.
Maslat AO, Abussaud M, Tashtoush H, AL-Talib M. Synthesis, antibacterial, antifungal and genotoxic activity of bis-1, 3, 4-oxadiazole derivatives. Pol J Pharmacol. 2002; 54: 55-60.
McGuffin P, Katz R. The genetics of depression and manic-depressive disorder. The Bri J Psy. 1989; 155: 294-304.
Murray CJ, Lopez AD. Alternative projections of mortality and disability by cause 1990–2020: Global burden of disease study. Lancet 1997; 349: 1498-504.
Omar AM, Aboulwafa OM. Synthesis and anticonvulsant properties of a novel series of 2‐substituted amino‐5‐aryl‐1, 3, 4‐oxadiazole derivatives. J Het Chem. 1984; 21: 1415-18.
Omar FA, Mahfouz NM, Rahman MA. Design, synthesis and anti-inflammatory activity of some 1, 3, 4-oxadiazole deriva-tives. Eur J Med Chem. 1996; 31: 819-25.
Otte C, Gold SM, Penninx BW, Pariante CM, Etkin A, Fava M, Mohr DC, Schatzberg AF. Major depressive disorder. Nat Rev Dis Primers. 2016; 2:1-20.
Patel KD, Prajapati SM, Panchal SN, Patel HD. Review of synthesis of 1, 3, 4-oxadiazole derivatives. Syn Commun. 2014; 44: 1859-75.
Predictable SE. Side effects of antidepressants: An overview. Clevel Clin J Med. 2006; 73:351-53.
Puthiyapurayil P, Poojary B, Chikkanna C, Buridipad SK. Design, synthesis and biological evaluation of a novel series of 1, 3, 4-oxadiazole bearing N-methyl-4-(trifluoromethyl) phenyl pyrazole moiety as cytotoxic agents. Eur J Med Chem. 2012; 53:203-10.
Roy PP, Bajaj S, Maity TK, Singh J. Synthesis and evaluation of anticancer activity of 1, 3, 4-oxadiazole derivatives against ehrlich ascites carcinoma bearing mice and their correlation with histopathology of liver receptor. Indian J Pharm Edu Res. 2017; 51: 260-69.
Saitoh M, Kunitomo J, Kimura E, Iwashita H, Uno Y, Onishi T, Uchiyama N, Kawamoto T, Tanaka T, Mol CD, Dougan DR. 2-{3-[4-(Alkylsulfinyl) phenyl]-1-benzofuran-5-yl}-5-methyl-1, 3, 4-oxadiazole derivatives as novel inhibitors of glycogen synthase kinase-3β with good brain permeability. J Med Chem. 2009; 52: 6270-86.
Steru L, Chermat R, Thierry B, Simon P. The tail suspension test: A new method for screening antidepressants in mice. Psychopharmacology 1985; 85: 367-70.
Tamminga CA, Nemeroff CB, Blakely RD, Brady L, Carter CS, Davis KL, Dingledine R, Gorman JM, Grigoriadis DE, Henderson DC, Innis RB. Developing novel treatments for mood disorders: Accelerating discovery. Bio Psy. 2002; 52: 589-609.
Tantray MA, Khan I, Hamid H, Alam MS, Dhulap A, Kalam A. Synthesis of benzimidazole-linked-1, 3, 4-oxadiazole carboxamides as GSK-3β inhibitors with in vivo antidepressant activity. Bioorg Chem. 2018; 77: 393-401.
Tantray MA, Khan I, Hamid H, Alam MS, Dhulap A, Kalam A. Synthesis of benzimidazole-based 1,3,4-oxadiazole-1,2,3-triazole conjugates as glycogen synthase kinase-3β inhibitors with antidepressant activity in in vivo models. RSC Adv. 2016; 6: 43345-55.
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Copyright (c) 2022 Banylla Felicity Dkhar Gatphoh, Natasha Naval Aggarwal, S. Madan Kumar, M. Vijay Kumar, B. C. Revanasiddappa
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