Design, synthesis, analgesic, anti-inflammatory activity of novel pyrazolones possessing aminosulfonyl pharmacophore as inhibitors of COX-2/5-LOX enzymes: Histopathological and docking studies

Bioorganic Chemistry - Tập 78 - Trang 103-114 - 2018
Mohamed A. Abdelgawad1,2, Madlen B. Labib2, Waleed A.M. Ali3, Gehan Kamel4, Amany A. Azouz5, EL-Shaymaa EL-Nahass6
1Department of Pharmaceutical Chemistry, College of Pharmacy, Jouf University, Sakaka, Aljouf 2014, Saudi Arabia
2Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Beni-Suef University, Beni-Suef 62514, Egypt
3Biochemistry Department, Cairo General Hospital, Egypt
4Department of Pharmacology, Faculty of Veterinary, Cairo University, Cairo, Egypt
5Department of Pharmacology and Toxicology, Faculty of Pharmacy, Beni-Suef University, Beni-Suef, Egypt
6Department of Pathology, Faculty of Veterinary Medicine, Beni-Suef University, Beni-Suef, 62511, Egypt

Tài liệu tham khảo

G.F. Meresman, C.N. Olivares. Involvement of prostaglandins in the pathophysiology of endometriosis, in: K. Chaudhury, B. Chakravarty (Eds.), Endometriosis – Basic concepts and current research trends, ISBN: 978-953-51-0524-4, E-Publishing Inc., InTech, 2012, pp. 115-132, Available from: <http://www.intechopen.com/books/endometriosis-basicconcepts-and-current-research-trends/involvement-of-prostaglandins-in-the-pathophysiology-of-endometriosis>. S. Koontongkaew, K. Leelahavanichkul, Arachidonic acid metabolism and its implication on head and neck cancer, in: M. Agulnik (Ed.), Head and neck cancer, ISBN: 978-953-51-0236-6, E-Publishing Inc., InTech, 2012, pp. 167–184. Available from: <http://www.intechopen.com/books/head-and-neck-cancer/arachidonic-acid-metabolism-and-its-implication-on-head-and-neck-cancer>. Chowdhury, 2008, Synthesis of celecoxib analogs that possess a N-hydroxypyrid-2(1H)one 5-lipoxygenase pharmacophore: biological evaluation as dual inhibitors of cyclooxygenases and 5-lipoxygenase with anti-inflammatory activity, Bioorg. Med. Chem. Lett., 18, 6138, 10.1016/j.bmcl.2008.10.009 Szabó, 2008, New celecoxib derivatives as anti-inflammatory agents, J. Med. Chem., 51, 142, 10.1021/jm070821f Zebardast, 2009, Design and synthesis of 3-alkyl-2-aryl-1,3-thiazinan-4-one derivatives as selective cyclooxygenase (COX-2) inhibitors, Bioorg. Med. Chem. Lett., 19, 3162, 10.1016/j.bmcl.2009.04.125 Gao, 2011, Synthesis and preliminary in vitro biological evaluation of new carbon-11-labeled celecoxib derivatives as candidate PET tracers for imaging of COX-2 expression in cancer, Eur. J. Med. Chem., 46, 4760, 10.1016/j.ejmech.2011.05.024 Blankenbuehler, 2002, Synthesis of 4-(1,4-diaryl-2H-cyclopent[d]pyridazin-2-yl)-benzenesulfonamides, Heterocycles, 57, 2383, 10.3987/COM-02-9591 Hassan, 2014, Celecoxib analogs bearing benzofuran moiety as cyclooxygenase-2 inhibitors: design, synthesis and evaluation as potential anti-inflammatory agents, Eur. J. Med. Chem., 76, 482, 10.1016/j.ejmech.2014.02.033 Salgın-Goksen, 2007, 1-Acylthiosemicarbazides, 1,2,4-triazole-5(4H)-thiones, 1,3,4-thiadiazoles and hydrazones containing 5-methyl-2-benzoxazolinones: synthesis, analgesic-anti-inflammatory and antimicrobial activities, Bioorg. Med. Chem., 15, 5738, 10.1016/j.bmc.2007.06.006 El-Moghazy, 2012, Synthesis and anti-inflammatory activity of some pyrazole derivatives, Med. Chem. Res., 21, 1722, 10.1007/s00044-011-9691-4 Chowdhury, 2010, Celecoxib analogs possessing a N-(4-nitrooxybutyl)piperidin-4-yl or N-(4-nitrooxybutyl)-1,2,3,6-tetrahydropyridin-4-yl nitric oxide donor moiety: synthesis, biological evaluation and nitric oxide release studies, Bioorg. Med. Chem. Lett., 20, 1324, 10.1016/j.bmcl.2010.01.014 Bing, 2002, Why do cyclo-oxygenase-2 inhibitors cause cardiovascular events?, JACC, 39, 521, 10.1016/S0735-1097(01)01749-1 Abd El Razik, 2017, Benzodioxole-pyrazole hybrids as anti-inflammatory and analgesic agents with COX-1,2/5-LOX inhibition and antioxidant potential, Archiv der Pharmzie, 350 Martel-Pelletier, 2003, Therapeutic role of dual inhibitors of 5-LOX and COX, selective and non-selective non-steroidal anti-inflammatory drugs, Ann. Rheum. Dis., 62, 501, 10.1136/ard.62.6.501 Reddy, 2015, Exploration of binding site pattern in arachidonic acid metabolizing enzymes, Cyclooxygenases and Lipoxygenases, BMC Res. Notes, 8, 152, 10.1186/s13104-015-1101-4 Charlier, 2003, Dual inhibition of cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX) as a new strategy to provide safer non-steroidal anti-inflammatory drugs, Eur. J. Med. Chem., 38, 645, 10.1016/S0223-5234(03)00115-6 Chowdhury, 2009, Synthesis of new 1-(2-, 3-, or 4-methanesulfonylphenyl)-2-[5-(N-hydroxypyridin-2(1H)-one)]acetylene regioisomers: a search for novel cyclooxygenase and lipoxygenase inhibitors, J. Het. Chem., 46, 58, 10.1002/jhet.23 Sivakumar, 2013, Synthesis, in-vitro antimicrobial and antitubercular screening of some schiff base of 5-amino-4-[2-(4-phenyl-1,3-thiazol-2-yl)hydrazinylidene]-2,4-dihydro-3H-pyrazol-3-one, IJDDD, 4, 1065 Ragab, 2013, Pyrazolone derivatives: synthesis, anti-inflammatory, analgesic, quantitative structure–activity relationship and in vitro studies, Chem. Pharm. Bull., 61, 834, 10.1248/cpb.c13-00314 Gupta, 2015, Synthesis and biological significance of pyrazolones: a review, IJPSR, 6, 2291 Manojkumar, 2009, Antioxidant and antibacterial studies of arylazopyrazoles and arylhydrazonopyrazolones containing coumarin moiety, Eur. J. Med. Chem., 44, 4690, 10.1016/j.ejmech.2009.07.004 Almasirad, 2005, Synthesis and analgesic activity of N-arylhydrazone derivatives of mefenamic acid, J. Pharm. Pharmaceut. Sci., 8, 419 Asif, 2013, Analgesic, anti-inflammatory, and antiplatelet profile of hydrazones containing synthetic molecules, J. Appl. Chem., 2013, 1, 10.1155/2013/247203 Habeeb, 2001, Design and synthesis of celecoxib and rofecoxib analogues as selective cyclooxygenase-2 (cox-2) inhibitors: replacement of sulfonamide and methylsulfonyl pharmacophores by an azido bioisostere, J. Med. Chem., 44, 3039, 10.1021/jm010153c Mohammed, 2014, Synthesis, molecular docking, and biological evaluation of some novel hydrazones and pyrazole derivatives as anti-inflammatory agents, Chem. Biol. Drug Des., 84, 473, 10.1111/cbdd.12336 Mustafa, 2012, Synthesis of new sulfonamides as lipoxygenase inhibitors, Bioorg. Med. Chem., 20, 2535, 10.1016/j.bmc.2012.02.055 Abdellatif, 2015, Synthesis, cyclooxygenase inhibition, anti-inflammatory evaluation and ulcerogenic liability of novel triarylpyrazoline derivatives as selective COX-2 inhibitors, Bioorg. Med. Chem. Lett., 25, 5787, 10.1016/j.bmcl.2015.10.047 Abdellatif, 2017, Synthesis and biological evaluation of new diarylpyrazole and triarylimidazoline derivatives as selective COX-2 Inhibitors, Archiv der Pharmzie, 350 Abdelgawad, 2017, Pyrazole-hydrazone derivatives as anti-inflammatory agents: design, synthesis, biological evaluation, COX-1,2/5-LOX inhibition and docking study, Bioorg. Chem., 74, 212, 10.1016/j.bioorg.2017.08.014 Belal, 2017, New benzothiazole/benzoxazole-pyrazole hybrids with potential as COX inhibitors: design, synthesis and anticancer activity evaluation, Res. Chem. Intermediat., 10.1007/s11164-016-2851-x Abdellatif, 2015, Synthesis and anti-inflammatory evaluation of new 1,3,5-triaryl-4,5-dihydro-1H-pyrazole derivatives possessing an aminosulphonyl pharmacophore, Arch. Pharm. Res., 38, 10.1007/s12272-015-0606-7 Abdelrahman, 2017, Synthesis, biological evaluation, docking study and ulcerogenicity profiling of some novel quinoline-2-carboxamides as dual COXs/LOX inhibitors endowed with anti-inflammatory activity, Eur. J. Med. Chem., 127, 972, 10.1016/j.ejmech.2016.11.006 Yao, 1962, Azo-hydrazone conversion. I. The Japp-Klingemann reaction, J. Am. Chem. Soc., 84, 3514, 10.1021/ja00877a018 Fakhr, 2009, Synthesis and pharmacological evaluation of 2-substituted benzo[b]thiophenes as anti-inflammatory and analgesic agents, Eur. J. Med. Chem., 44, 1718, 10.1016/j.ejmech.2008.02.034 Rao, 2003, J. Med. Chem., 46, 4872, 10.1021/jm0302391 Yamamoto, 1992, Mammalian lipoxygenases: molecular structures and functions, Biochim. Biophys. Acta, 1128, 117, 10.1016/0005-2760(92)90297-9 Winter, 1962, Carrageenan-induced edema in hind paw of the rat as an assay for anti-inflammatory drugs, Proc. Soc. Exp. Biol., 111, 544, 10.3181/00379727-111-27849 R.A. Turner, P. Hebban, Analgesic Screening Methods in Pharmacology, vol. 100, Academic Press, New York, 1965. Cho, 1979, Cholinergic-mediated gastric mast cell degranulation with subsequent histamine H1-and H2-receptor activation in stress ulceration in rats, Eur. J. Pharmacol., 55, 23, 10.1016/0014-2999(79)90144-4 Bancroft, 2008 RCSB Protein Data Bank. Available online: <http://www.rcsb.org/pdb> (accessed on 1 Dec 2017). Wang, 2010, Thenovel benzopyran class of selective cyclooxygenase-2 inhibitors. Part 2: the second clinical candidate having a shorter and favorable human half-life, Bioorg. Med. Chem. Lett., 20, 7159, 10.1016/j.bmcl.2010.07.054