Novel tetrazole and cyanamide derivatives as inhibitors of cyclooxygenase-2 enzyme: design, synthesis, anti-inflammatory evaluation, ulcerogenic liability and docking study

References

• Cheng-Xi W, Ming B, Guo-Hua G. Tetrazolium compounds: synthesis and applications in medicine. Molecules 2015; 20:5528–53.
   PubMed Web of Science ®Google Scholar
• Demko ZP, Sharpless KB. Preparation of 5-substituted 1H-tetrazoles from nitriles in water. J Org Chem 2001;66:7945–50.
   PubMed Web of Science ®Google Scholar
• Vinoth KS, Ranjith KR, Silpa B, et al. The therapeutic journey of tetrazoles: a review. J Compr Pharm 2015;2:42–7.
   Google Scholar
• Bachar SC, Lahiri SC. Synthesis of chloro and bromo substituted 5-(indan-1′-yl)tetrazoles and 5-(indan-1′-yl)methyltetrazoles as possible analgesic agents. Pharmazie 2004;59:435–8.
   PubMed Web of Science ®Google Scholar
• Nazariy TP, Vasyl SM, Mykola DO. New convenient synthesis of 2,3-diaminotheino[2,3-d]pyrimidin-4 (3H)-one derivates from substituted alkyl 2-(1H-tetrazol-1-yl)thiophene-3-carboxylates. Tetrahydron 2008;64:1430–4.
   Web of Science ®Google Scholar
• Bhaskar VH, Mohite PB, Pandhare RB, Khanage SG. In vitro evaluation of tetrazoles as a novel class of Antimycobacterium tuberculosis agents. Acta Pharm Sci 2010;52:502–10.
   Google Scholar
• Mohite PB, Bhaskar VH. Potential pharmacological activities of tetrazoles in the new millennium. Int J PharmTech Res 2011;3:1557–66.
   Google Scholar
• Moustafa MA, El-Sherbeny MA, El-Sherbiny DT, El-Sayed SM. Molecular modeling, synthesis and antimicrobial evaluation of new molecular hybrids of tetrazole derivatives. J Am Sci 2012;8:973–86.
   Google Scholar
• Dhayanithi V, Syed SS, Kumaran K, et al. Synthesis of selected 5-thio-substituted tetrazole derivatives and evaluation of their antibacterial and antifungal activities. J Serb Chem Soc 2011;76:165–75.
   Web of Science ®Google Scholar
• Wu J, Wang Q, Guo J, et al. Characterization of angiotensin II antagonism displayed by Ib, a novel nonpeptide angiotensin AT(1) receptor antagonist. Eur J Pharmacol 2008;589:220–24.
   PubMed Web of Science ®Google Scholar
• Yan B, Wang G, Sun J, et al. Identification of the major metabolites of 5-n-butyl-4-{4-[2-(1H-tetrazole-5-yl)-1H-pyrrol-1-yl]phenylmethyl}-2,4-dihydro-2-(2,6-dichloridephenyl)-3H-1,2,4-triazol-3-one, a new angiotensin type 1 receptor antagonist, in rat bile by HPLC-diode array detection-MS and HPLC-MS/MSJ. Biomed Chromatogr 2007;21:912–24.
   PubMed Web of Science ®Google Scholar
• Berghmans S, Hunt J, Roach A, Goldsmith P. Zebra fish offer the potential for a primary screen to identify a wide variety of potential anticonvulsants. Epilepsy Res 2007;75:18–28.
   PubMed Web of Science ®Google Scholar
• Rostom SA, Ashour HM, El Razik HA, et al. Azole antimicrobial pharmacophore-based tetrazoles: synthesis and biological evaluation as potential antimicrobial and anticonvulsant agents. Bioorg Med Chem 2009;17:2410–22.
   PubMed Web of Science ®Google Scholar
• Bhaskar VH, Mohite PB. Synthesis, characterization and evaluation of anticancer activity of some tetrazole derivatives. J Optoelect Biomed Mat 2010;2:249–59.
   Google Scholar
• Romagnoli R, Baraldi PG, Salvador MK, et al. Synthesis and evaluation of 1,5-disubstituted tetrazoles as rigid analogues of combretastatin A-4 with potent antiproliferative and antitumor activity. J Med Chem 2012;55:475–88.
   PubMed Web of Science ®Google Scholar
• Gürsoy A, Demiravak S, Capan G, et al. Synthesis and preliminary evaluation of new 5-pyrazolinone derivatives as analgesic agents. Eur J Med Chem 2000;35:359–64.
   PubMed Web of Science ®Google Scholar
• Uchida M, Komatsu M, Morita S, et al. Studies on gastric antiulcer active agents. II.: synthesis of tetrazole alkanamides and related compounds. Chem Pharm Bull 1989;37:322–6.
   PubMed Web of Science ®Google Scholar
• Bepary S, Das BK, Bachar SC, et al. Anti-inflammatory activity of indanyltetrazole derivatives. Pak J Pharm Sci 2008;21:295–8.
   PubMed Web of Science ®Google Scholar
• Kumar P, Knaus EE. Synthesis and antiinflammatory activity of 5-(1,6-dihydropyridyl)-tetrazol-2-acetic acids, esters and amides. Drug Des Discov 1994;11:15–20.
   PubMedGoogle Scholar
• Vicini P, Amoretti L, Barocelli E, et al. Synthesis and anti-inflammatory, antipyretic and analgesics properties of 5-(1,2-benzisothiazolyl)tetrazoles. Farmaco Sci 1986;41:111–8.
   PubMedGoogle Scholar
• Pande K, Tandon M, Bhalla TN, et al. Tetrazoles as potent anti-inflammatory agents. Pharmacology 1987;35:333–8.
   PubMed Web of Science ®Google Scholar
• Ikeda T, Kakegawa H, Miyataka H, et al. Anti-allergic and anti-inflammatory actions of 2′-(tetrazole-5-yl)-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxanilide 1,1-dioxide. Bioorg Med Chem Lett 1992;2:709–14.
   Web of Science ®Google Scholar
• Abou-Ghalia MH, Amr AE, Abdulla MM. Synthesis of some new (Nα-dipicolinoyl)-bis-L-leucyl-DL-norvalyl linear tetra and cyclic octa bridged peptides as new anti-inflammatory Agents. Z Naturforsch 2003;58b:903–10.
   Google Scholar
• Sondhia SM, Jaina S, Dinodiaa M, Kumarb A. Synthesis of some thiophene, imidazole and pyridine derivatives exhibiting good anti-inflammatory and analgesic activities. Med Chem 2008;4:146–54.
   PubMed Web of Science ®Google Scholar
• Thirumurugan P, Mahalaxmi S, Perumal PT. Synthesis and anti-inflammatory activity of 3-indolyl pyridine derivatives through one-pot multi component reaction. J Chem Sci 2010;122:819–32.
   Web of Science ®Google Scholar
• Rathish IG, Javed K, Ahmad S, et al. Synthesis and anti-inflammatory activity of some new 1,3,5-trisubstituted pyrazolines bearing benzene sulfonamide. Bioorg Med Chem Lett 2009;19:255–8.
   PubMed Web of Science ®Google Scholar
• Ovais S, Bashir R, Yaseen S, et al. Synthesis and pharmacological evaluation of some novel 2-pyrazolines bearing benzenesulfonamide as anti-inflammatory and blood glucose lowering agents. Med Chem Res 2012; 22:1378–85.
   Web of Science ®Google Scholar
• Ovais S, Yaseen S, Bashir R, et al. Synthesis and anti-inflammatory activity of celecoxib like compounds. J Enzyme Inhib Med Chem 2013;28:1105–12.
   PubMed Web of Science ®Google Scholar
• Bashir R, Ovais S, Yaseen S, et al. Synthesis of some new 1,3,5-trisubstituted pyrazolines bearing benzene sulfonamide as anticancer and anti-inflammatory agents. Bioorg Med Chem Lett 2011;21:4301–5.
   PubMed Web of Science ®Google Scholar
• Kajal A, Bala S, Sharma N, et al. Therapeutic potential of hydrazones as anti-Inflammatory agents. Int J Med Chem 2014;2014:1–11.
   Google Scholar
• Won SJ, Liu CT, Tsao LT, et al. Synthetic chalcones as potential anti-inflammatory and cancer chemopreventive agents. Eur J Med Chem 2005;40:103–12.
   PubMed Web of Science ®Google Scholar
• Mohite PB, Pandhare RB, Khanage SG. Synthesis, characterization and anti-inflammatory activity of novel N-substituted tetrazoles. Analele UniversităŃii Din Bucureşti – Chimie (Serie Nouă) 2011;20:107–13.
   Google Scholar
• Ghosh R, Das A. Synthesis and biological activities of chalcones and their heterocyclic derivatives: a review. World J Pharm Pharm Sci 2014;3:578–95.
   Google Scholar
• Al-Hourania BJ, McDonald R, El-Barghouthi MI, et al. Molecular docking studies and X-ray structure determination of 1-{4-(methylsulfonyl)phenyl}-5-phenyl-1H-tetrazole. Jord J Chem 2015;10:34–40.
   Google Scholar
• Al-Hourani BJ, El-Barghouthi MI, Mcdonald R, et al. Docking studies and the crystal structure of two tetrazole derivatives:5-(4-chlorophenyl)-1-{4-(methylsulfonyl)phenyl}-1H-tetrazole and4-{5-(4-methoxyphenyl)-1H-tetrazol-1-yl}benzenesul-fonamide. J Mol Struc 2015;1101:21–7.
   Web of Science ®Google Scholar
• Wuest F, Tang X, Kniess T, et al. Synthesis and cyclooxygenase inhibition of various (aryl-1,2,3-triazole-1-yl)-methanesulfonylphenyl derivatives. Bioorg Med Chem 2009;17:1146–51.
   PubMed Web of Science ®Google Scholar
• Al-Hourani BJ, Sharma SK, Suresh M, Wuest F. Novel 5-substituted 1H-tetrazoles as cyclooxygenase-2 (COX-2) inhibitors. Bioorg Med. Chem Lett 2012;22:2235–8.
   PubMed Web of Science ®Google Scholar
• Al-Hourani BJ, Sharma SK, Kaur J, Wuest F. Synthesis, bioassay studies, and molecular docking of novel 5-substituted 1H tetrazoles as cyclooxygenase-2 (COX-2) Inhibitors. Med Chem Res 2015;24:78–94.
   Web of Science ®Google Scholar
• Al-Hourani BJ, Sharma SK, Mane JY, et al. Synthesis and evaluation of 1,5-diaryl-substituted tetrazoles as novel selective cyclooxygenase-2 (COX-2) inhibitors. Bioorg Med Chem Lett 2011;21:1823–6.
   PubMed Web of Science ®Google Scholar
• Eman KA, Phoebe FL, Waleed AM. Cyclooxygenase-2 and 15-lipoxygenase inhibition, synthesis, anti-inflammatory activity and ulcer liability of new celecoxib analogues: determination of region-specific pyrazole ring formation by NOESY. Bioorg Med Chem Lett 2016;26:2893–9.
   PubMed Web of Science ®Google Scholar
• Catella-Lawson F, McAdam B, Morrison BW, et al. Effects of specific inhibition of cyclooxygenase-2 on sodium balance, hemodynamics, and vasoactive eicosanoids. J Pharmacol Exp Ther 1999;289:735–41.
   PubMed Web of Science ®Google Scholar
• Lamie PF, Phillopes JN, El-Gendy AO, et al. Design, synthesis and evaluation of novel phthalimide derivatives as in vitro anti-microbial, anti-oxidant and anti-inflammatory agents. Molecules 2015;20:16620–42.
   PubMed Web of Science ®Google Scholar
• Navidpour L, Amini M, Shafaroodi H, et al. Design and synthesis of new water-soluble tetrazolide derivatives of celecoxib and rofecoxib as selective cyclooxygenase-2 (COX-2) inhibitors. Bioorg Med Chem Lett 2006;16:4483–7.
   PubMed Web of Science ®Google Scholar
• Hinz B, Brune K. Cyclooxygenase-2-10 years later. J Pharmacol Exp Ther 2002;300:367–75.
   PubMed Web of Science ®Google Scholar
• Khode S, Maddi V, Aragade P, et al. Synthesis and pharmacological evaluation of a novel series of 5-(substituted)aryl-3-(3-coumarinyl)-1-phenyl-2-pyrazolines as novel anti-inflammatory and analgesic agents. Eur J Med Chem 2009;44:1682–8.
   PubMed Web of Science ®Google Scholar
• Lamie PF, Ali WAM, Bazgier V, Rarova L. Novel N-substituted indole Schiff bases as dual inhibitors of cyclooxygenase-2 and 5-lipoxygenase enzymes: synthesis, biological activities in vitro and docking study. Eur J Med Chem 2016;123:803–13.
   PubMed Web of Science ®Google Scholar
• Yamamoto S. Mammalian lipoxygenases: molecular structures and functions. Biochim Biophys Acta 1992;1128:117–31.
   PubMed Web of Science ®Google Scholar
• Gaffney BJ. Lipoxygenases: structural principles and spectroscopy. Annu Rev Biophys Biomol Struct 1996;25:431–59.
   PubMedGoogle Scholar
• Winter CA, Risely EA, Nuss GW. Carrageenin-induced edema in hind paw of the rat as an assay for antiiflammatory drugs. Proc Soc Exp Biol Med 1962;111:544–47.
   PubMed Web of Science ®Google Scholar
• Cho CH, Ogle CW. Cholinergic-mediated gastric mast cell degranulation with subsequent histamine H 1- and H 2-receptor activation in stress ulceration in rats. Eur J Pharmacol 1979;55:23–33.
   PubMed Web of Science ®Google Scholar
• Eddy N, Leimback D. Synthetic analgesics. II. Dithylenylbutenylamines and dithylenylbutyl amines. Pharmacol Exper Therap 1953;3:131–47.
   Google Scholar
• Koster R, Anderson M,D, Beer E, Acetic acid-induced analgesic screening. In: Federation Proceedings, 1959.
   Google Scholar
• Bancroft JD, Gamble M, Theory and practice of histological techniques. 6th ed. North Hollywood, Philadelphia (PA): Churchill Livingstone/Elsevier; 2008.
   Google Scholar
• Vembu S, Parasuraman P, Gopalakrishnan M. Design, in silico molecular docking studies, synthesis, spectral characterization and in vitro antifungal evaluation of 1-(4-(1H-tetrazole-1-yl)phenyl)-3-arylprop-2-en-1-ones. Der Pharma Chemica 2014;6:35–44.
   Google Scholar
• Vorobiov AN, Gaponik PN, Petrov PT, Ivashkevich OA. One-pot syntheses of 5-amino-1-aryltetrazole derivatives. Synthesis 2006; 1307–12.
   Web of Science ®Google Scholar
• Gartner PL, Hiatt JL. Color atlas and text of histology, 6th ed. Philadelphia: Lippincott Williams & Wilkins; 2014.
   Google Scholar
• Günnur ÖD, Elif ÇY. Histopathologic evaluation of anti-ulcerogenic effect of montelukast in indomethacin-induced experimental ulcer model. Turk J Gastroenterol 2013; 24:88–92.
   PubMed Web of Science ®Google Scholar
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   Google Scholar