Docking Study, Synthesis, and Anti-Inflammatory Potential of Some New Pyridopyrimidine-Derived Compounds

References

• Medzhitov R. Origin and physiological roles of inflammation. Nature. 2008;454(7203):428. doi:10.1038/nature07201
   PubMed Web of Science ®Google Scholar
• Nathan C. Points of control in inflammation. Nature. 2002;420(6917):846. doi:10.1038/nature01320
   PubMed Web of Science ®Google Scholar
• Kolls JK, Lindén A. Interleukin-17 family members and inflammation. Immunity. 2004;21(4):467–476. doi:10.1016/j.immuni.2004.08.018
   PubMed Web of Science ®Google Scholar
• Nathan C, Ding A. Nonresolving inflammation. Cell. 2010;140(6):871–882. doi:10.1016/j.cell.2010.02.029
   PubMed Web of Science ®Google Scholar
• Levine B, Mizushima N, Virgin HW. Autophagy in immunity and inflammation. Nature. 2011;469(7330):323. doi:10.1038/nature09782
   PubMed Web of Science ®Google Scholar
• Olefsky JM, Glass CK. Macrophages, inflammation, and insulin resistance. Annu Rev Physiol. 2010;72(1):219–246. doi:10.1146/annurev-physiol-021909-135846
   PubMed Web of Science ®Google Scholar
• Abdellatif KR, Abdelgawad MA, Labib MB, Zidan TH. Synthesis and biological evaluation of new diarylpyrazole and triarylimidazoline derivatives as selective cox‐2 inhibitors. Arch Pharm. 2017;350(8):1600386. doi:10.1002/ardp.201600386
   Web of Science ®Google Scholar
• Vane JR, Botting RM. Mechanism of action of nonsteroidal anti-inflammatory drugs. Am J Med. 1998;104(3):2S–8S. doi:10.1016/S0002-9343(97)00203-9
   PubMedGoogle Scholar
• Brune K, Patrignani P. New insights into the use of currently available non-steroidal anti-inflammatory drugs. J Pain Res. 2015;8:105. doi:10.2147/JPR.S75160
   PubMed Web of Science ®Google Scholar
• Hla T, Neilson K. Human cyclooxygenase-2 cDNA. Proc Nat Acad Sci. 1992;89(16):7384–7388. doi:10.1073/pnas.89.16.7384
   PubMed Web of Science ®Google Scholar
• Abdellatif K, Abdelall E, Bakr R. Nitric oxide-NSAIDs donor prodrugs as hybrid safe anti-inflammatory agents. Curr Top Med Chem. 2017;17(8):941–955. doi:10.2174/1568026616666160927153435
   PubMed Web of Science ®Google Scholar
• Abdelgawad MA, Bakr RB, Omar HA. Design, synthesis and biological evaluation of some novel benzothiazole/benzoxazole and/or benzimidazole derivatives incorporating a pyrazole scaffold as antiproliferative agents. Bioorg Chem. 2017;74:82–90. doi:10.1016/j.bioorg.2017.07.007
   PubMed Web of Science ®Google Scholar
• Bakr RB, Azouz AA, Abdellatif KR. Synthesis, cyclooxygenase inhibition, anti-inflammatory evaluation and ulcerogenic liability of new 1-phenylpyrazolo [3, 4-d] pyrimidine derivatives. J Enzyme Inhib Med Chem. 2016;31:6–12. doi:10.1080/14756366.2016.1186018
   PubMed Web of Science ®Google Scholar
• Abdellatif KR, Abdelgawad MA, Elshemy HA, Alsayed SS, Kamel G. Synthesis and anti-inflammatory evaluation of new 1, 3, 5-triaryl-4, 5-dihydro-1h-pyrazole derivatives possessing an aminosulphonyl pharmacophore. Arch Pharm Res. 2015;38(11):1932–1942. doi:10.1007/s12272-015-0606-7
   PubMed Web of Science ®Google Scholar
• Wang D, DuBois RN. The role of cox-2 in intestinal inflammation and colorectal cancer. Oncogene. 2010;29(6):781. doi:10.1038/onc.2009.421
   PubMed Web of Science ®Google Scholar
• Griswold DE, Adams JL. Constitutive cyclooxygenase (cox‐1) and inducible cyclooxygenase (cox‐2): rationale for selective inhibition and progress to date. Med Res Rev. 1996;16(2):181–206. doi:10.1002/(SICI)1098-1128(199603)16:2<181::AID-MED3>3.0.CO;2-X
   PubMed Web of Science ®Google Scholar
• Lazzaroni M, Bianchi Porro G. Gastrointestinal side‐effects of traditional non‐steroidal anti‐inflammatory drugs and new formulations. Aliment Pharmacol Ther. 2004;20:48–58. doi:10.1111/j.1365-2036.2004.02037.x
   PubMed Web of Science ®Google Scholar
• Vane J, Bakhle Y, Botting R. Cyclooxygenases 1 and 2. Annu Rev Pharmacol Toxicol. 1998;38(1):97–120. doi:10.1146/annurev.pharmtox.38.1.97
   PubMed Web of Science ®Google Scholar
• Abdelrahman MH, Youssif BG, Abdelazeem AH, et al. 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. 2017;127:972–985. doi:10.1016/j.ejmech.2016.11.006
   PubMed Web of Science ®Google Scholar
• Abdelgawad MA, Bakr RB, El-Gendy AO, Kamel GM, Azouz AA, Bukhari SNA. Discovery of a cox-2 selective inhibitor hit with anti-inflammatory activity and gastric ulcer protective effect. Future Med Chem. 2017;9(16):1899–1912. doi:10.4155/fmc-2017-0115
   PubMed Web of Science ®Google Scholar
• Lacerda RB, de Lima CK, da Silva LL, et al. Discovery of novel analgesic and anti-inflammatory 3-arylamine-imidazo [1, 2-a] pyridine symbiotic prototypes. Bioorg Med Chem. 2009;17(1):74–84. doi:10.1016/j.bmc.2008.11.018
   PubMed Web of Science ®Google Scholar
• Abdelgawad MA, Bakr RB, Azouz AA. Novel pyrimidine-pyridine hybrids: synthesis, cyclooxygenase inhibition, anti-inflammatory activity and ulcerogenic liability. Bioorg Chem. 2018;77:339–348. doi:10.1016/j.bioorg.2018.01.028
   PubMed Web of Science ®Google Scholar
• Girgis AS, Mishriky N, Ellithey M, Hosni HM, Farag H. Novel synthesis of [1]-benzothiepino [5, 4-b] pyridine-3-carbonitriles and their anti-inflammatory properties. Bioorg Med Chem. 2007;15(6):2403–2413. doi:10.1016/j.bmc.2007.01.015
   PubMed Web of Science ®Google Scholar
• Renard J-F, Lecomte F, Hubert P, de Leval X, Pirotte B. N-(3-arylaminopyridin-4-yl) alkanesulfonamides as pyridine analogs of nimesulide: cyclooxygenases inhibition, anti-inflammatory studies and insight on metabolism. Eur J Med Chem. 2014;74:12–22. doi:10.1016/j.ejmech.2013.12.033
   PubMed Web of Science ®Google Scholar
• Chung S-T, Huang W-H, Huang C-K, et al. Synthesis and anti-inflammatory activities of 4h-chromene and chromeno [2, 3-b] pyridine derivatives. Res Chem Intermed. 2016;42(2):1195–1215. doi:10.1007/s11164-015-2081-7
   Web of Science ®Google Scholar
• Lu X, Zhang H, Li X, et al. Design, synthesis and biological evaluation of pyridine acyl sulfonamide derivatives as novel cox-2 inhibitors. Bioorg Med Chem. 2011;19(22):6827–6832. doi:10.1016/j.bmc.2011.09.034
   PubMed Web of Science ®Google Scholar
• Bekhit AA, Fahmy HT, Rostom SA, Baraka AM. Design and synthesis of some substituted 1h-pyrazolyl-thiazolo [4, 5-d] pyrimidines as anti-inflammatory–antimicrobial agents. Eur J Med Chem. 2003;38(1):27–36. doi:10.1016/S0223-5234(02)00009-0
   PubMed Web of Science ®Google Scholar
• Sondhi SM, Singh N, Johar M, Kumar A. Synthesis, anti-inflammatory and analgesic activities evaluation of some mono, bi and tricyclic pyrimidine derivatives. Bioorg Med Chem. 2005;13(22):6158–6166. doi:10.1016/j.bmc.2005.06.063
   PubMed Web of Science ®Google Scholar
• Keche AP, Hatnapure GD, Tale RH, Rodge AH, Birajdar SS, Kamble VM. A novel pyrimidine derivatives with aryl urea, thiourea and sulfonamide moieties: synthesis, anti-inflammatory and antimicrobial evaluation. Bioorg Med Chem Lett. 2012;22(10):3445–3448. doi:10.1016/j.bmcl.2012.03.092
   PubMed Web of Science ®Google Scholar
• Garjani A, Davaran S, Rashidi M, Malek N. Protective effects of some azo derivatives of 5-aminosalicylic acid and their pegylated prodrugs on acetic acid-induced rat colitis. DARU J Pharmaceut Sci. 2004;12:24–30.
   Google Scholar
• Abdu-Allah HH, El-Shorbagi A-NA, Abdel-Moty SG, El-Awady R, Abdel-Alim A. 5-aminosalyclic acid (5-asa): a unique anti-inflammatory salicylate. Med Chem. 2016;6(05):306–315. doi:10.4172/2161-0444.1000361
   Google Scholar
• Sheng SF, Zheng HX, Liu J, Zhao ZB. Synthesis of phenol-class azo derivatives of 4-aminosalicylic acid. Chin Chem Lett. 2008;19(4):419–422. doi:10.1016/j.cclet.2008.01.042
   Web of Science ®Google Scholar
• Hassan GS, Soliman GA. Design, synthesis and anti-ulcerogenic effect of some of furo-salicylic acid derivatives on acetic acid-induced ulcerative colitis. Eur J Med Chem. 2010;45(9):4104–4112. doi:10.1016/j.ejmech.2010.05.071
   PubMed Web of Science ®Google Scholar
• Mohamed MS, Awad SM, Sayed AI. Synthesis of certain pyrimidine derivatives as antimicrobial agents and anti-inflammatory agents. Molecules. 2010;15(3):1882–1890. doi:10.3390/molecules15031882
   PubMed Web of Science ®Google Scholar
• Abdelgawad MA, Labib MB, Ali WA, Kamel G, Azouz AA, EL-Shaymaa E-N. Design, synthesis, analgesic, anti-inflammatory activity of novel pyrazolones possessing aminosulfonyl pharmacophore as inhibitors of cox-2/5-lox enzymes: histopathological and docking studies. Bioorg Chem. 2018;78:103–114. doi:10.1016/j.bioorg.2018.03.011
   PubMed Web of Science ®Google Scholar
• Abdelgawad MA, Labib MB, Abdel-Latif M. Pyrazole-hydrazone derivatives as anti-inflammatory agents: design, synthesis, biological evaluation, cox-1, 2/5-lox inhibition and docking study. Bioorg Chem. 2017;74:212–220. doi:10.1016/j.bioorg.2017.08.014
   PubMed Web of Science ®Google Scholar
• Abdelgawad MA, Mohamed AM, Musa A, Mostafa EM, Awad HM. Synthesis, chromatographic separation and antimicrobial evolution of new azoquinoline-8-ol. J Pharmaceut Sci Res. 2018;10:1314–1318.
   Google Scholar
• Bakr RB, Elkanzi NA, Ghoneim AA, Moustafa S. Synthesis, molecular docking studies and in vitro antimicrobial evaluation of novel pyrimido [1, 2-a] quinoxaline and triazino [4, 3-a]-quinoxaline derivatives. Heterocycles. 2018;96(11):1941–1957. doi:10.3987/COM-18-13955
   Web of Science ®Google Scholar
• Elkanzi NA, Bakr RB, Ghoneim AA. Design, synthesis, molecular modeling study, and antimicrobial activity of some novel pyrano [2, 3‐b] pyridine and pyrrolo [2, 3‐b] pyrano [2.3‐d] pyridine derivatives. J Heterocycl Chem. 2019;56:406–416.
   Google Scholar
• Bakr RB, Ghoneim AA, Azouz AA. Selective cyclooxygenase inhibition and ulcerogenic liability of some newly prepared anti-inflammatory agents having thiazolo [4, 5-d] pyrimidine scaffold. Bioorg Chem. 2019;88:102964. doi:10.1016/j.bioorg.2019.102964
   PubMed Web of Science ®Google Scholar
• Belal A, Abdelgawad MA. New benzothiazole/benzoxazole-pyrazole hybrids with potential as cox inhibitors: design, synthesis and anticancer activity evaluation. Res Chem Intermed. 2017;43(7):3859–3872. doi:10.1007/s11164-016-2851-x
   Web of Science ®Google Scholar
• Oraby AK, Abdellatif KR, Abdelgawad MA, Attia KM, Dawe LN, Georghiou PE. 2, 4‐disubstituted phenylhydrazonopyrazolone and isoxazolone derivatives as antibacterial agents: synthesis, preliminary biological evaluation and docking studies. ChemistrySelect. 2018;3(11):3295–3301. doi:10.1002/slct.201800174
   Web of Science ®Google Scholar
• Abdellatif RA, Abdelgawad M, Elshemy. AH, Kahk M, El Amir M. Design, synthesis, antioxidant and anticancer activity of new coumarin derivatives linked with thiazole, isoxazole or pyrazole moiety. Lett Drug Des Discov. 2017;14(7):773–781. doi:10.2174/1570180813666161026153743
   Web of Science ®Google Scholar
• Bakr B, Mehany. BM, Abdellatif RA. Synthesis, egfr inhibition and anti-cancer activity of new 3, 6-dimethyl-1-phenyl-4-(substituted-methoxy) pyrazolo [3, 4-d] pyrimidine derivatives. Curr Med Chem Anticancer Agents. 2017;17:1389–1400.
   Google Scholar
• Taddei D, Slawin AM, Woollins JD. 2‐(benzylsulfanyl)‐6‐chloro‐9‐isopropylpurine, a valuable intermediate in the synthesis of diaminopurine cyclin dependent kinase inhibitors. European J Org Chem. 2005;2005(5):939–947. doi:10.1002/ejoc.200400748
   Web of Science ®Google Scholar
• Bhuvaneswari K, Nagasundaram N, Lalitha A. Synthesis, anti‐inflammatory activity, and molecular docking study of novel azo bis antipyrine derivatives against cyclooxygenase‐2 enzyme. J Chin Chem Soc. 2021;68:27–33.
   Web of Science ®Google Scholar
• Korade SN, Patil JD, Gaikwad DS, et al. Synthesis and biological activities of novel aryldiazo substituted heterocycles. Org Prep Proced Int. 2020;52(2):147–165. doi:10.1080/00304948.2020.1716625
   Web of Science ®Google Scholar
• Korade SN, Pore DM. Basic ionic liquid [DPPA] cl− catalyzed synthesis of fluorescent 3‐acetoacetyl− 6‐aryldiazenyl‐coumarins. ChemistrySelect. 2019;4:4804–4808. doi:10.1002/slct.201900332
   Web of Science ®Google Scholar
• Kurumbail RG, Stevens AM, Gierse JK, et al. Structural basis for selective inhibition of cyclooxygenase-2 by anti-inflammatory agents. Nature. 1996;384(6610):644–648. doi:10.1038/384644a0
   PubMed Web of Science ®Google Scholar
• Khanmohammadi H, Erfantalab M, Bayat A, Babaei A, Sohrabi M. New 1, 2, 4-triazole-based azo–azomethine dyes. Part ii: synthesis, characterization, electrochemical properties and computational studies. Spectrochim Acta a Mol Biomol Spectrosc. 2012;97:876–884. doi:10.1016/j.saa.2012.07.041
   PubMed Web of Science ®Google Scholar
• Arbabi HA, Soltani SS, Salehi H, Rezazadeh S, Zonouzi A, Toosibashi M. Convenient synthesis of heterocyclic azo dyes in the class of pyranopyrazoles and chromenes. J Chem Res. 2018;42(2):68–72. doi:10.3184/174751918X15177611816526
   Web of Science ®Google Scholar
• Cho CH, Ogle CW. Cholinergic-mediated gastric mast cell degranulation with subsequent histamine h1-and h2-receptor activation in stress ulceration in rats. Eur J Pharmacol. 1979;55(1):23–33. doi:10.1016/0014-2999(79)90144-4
   PubMed Web of Science ®Google Scholar