Synthesis, biological activity, and molecular dynamic studies of new triazolopyrimidine derivatives

De Clercq E. Antivirals: past, present and future. Biochem Pharmacol. 2013;15;85(6):727-44. doi: 10.1016/j.bcp.2012.12.011. Guschin, 2015, Treatment efficacy, treatment failures and selection of macrolide resistance in patients with high load of Mycoplasma genitalium during treatment of male urethritis with josamycin, BMC Infect. Dis., 15, 40, 10.1186/s12879-015-0781-7 Martin I, Sawatzky P, Liu G, Mulvey MR. Antimicrobial resistance toNeisseria gonorrhoeaein Canada: 2009-2013. Can Commun. Dis Rep. 2015 5;41(2):35-41. doi: 10.14745/ccdr.v41i02a04. Ragab, 2023, Design, synthesis, molecular dynamic simulation studies, and antibacterial evaluation of new spirocyclic aminopyrimidines, J. Mol. Struct.., 1278, 10.1016/j.molstruc.2023.134912 O’Neill, 2016 O’Neill, 2014 De Clercq, 2019, Fifty Years in Search of Selective Antiviral Drugs, J. Med. Chem., 62, 7322, 10.1021/acs.jmedchem.9b00175 Eweas, 2014, Design, synthesis, molecular docking of new thiopyrimidine-5-carbonitrile derivatives and their cytotoxic activity against HepG2 cell line, J. App. Pharm. Sci., 4, 102 Ibrahim, 2010, Design, synthesis, and biological evaluation of novel pyrimidine derivatives as CDK2 inhibitors, Eur. J. Med. Chem., 45, 1158, 10.1016/j.ejmech.2009.12.026 Mahran, 2016, Synthesis and biological evaluation of novel pyrimidines derived from 6-aryl-5-cyano-2-thiouracil, Z. Naturforsch. C, 71, 133, 10.1515/znc-2015-0265 Ragab, 2022, Design, Synthesis, and Antibacterial Activity of Spiropyrimidinone Derivatives Incorporated Azo Sulfonamide Chromophore for Polyester Printing Application, Fib. Polym., 23, 2114, 10.1007/s12221-022-4032-4 Renyu, 2018, Recent Applications of Triazolopyrimidine-Based Bioactive Compounds in Medicinal and Agrochemical Chemistry, Mini-Rev. Med. Chem., 18, 781, 10.2174/1389557517666171101112850 Swinson, 2005, Fluorine – A vital element in the medicine chest, PharmaChem., 26 Inoue, 2020, Contribution of Organofluorine Compounds to Pharmaceuticals, ACS Omega, 5, 10633, 10.1021/acsomega.0c00830 Nelson, 2007, Clin. Infect. Dis., 44, 977, 10.1086/512369 Abdelhamid, 2006, Reactions With Hydrazonoyl Halides 45: Synthesis of Some New Triazolino[4,3-a]pyrimidines, Pyrazolo[3,4-d]pyridazines, Isoxazolo[3,4-d]pyridazines, and Thieno[2,3-b]pyridines, Synth. Commun., 36, 97, 10.1080/00397910500330593 Shawali, 2007, Synthesis and antimicrobial activity of new functionalized derivatives of [1,2,4]triazolo[4,3-a]pyrimidin-5(1H)-one, Heteroat. Chem, 18, 393, 10.1002/hc.20311 Gaillard, 2015, Replication stress and cancer, Nat. Rev. Cancer, 15, 276, 10.1038/nrc3916 Ravichandran, 2014, Mononuclear zinc (ii) complexes of 2-((2-(piperazin-1-yl)ethylimino)methyl)-4-substituted phenols: synthesis, structural characterization, DNA binding and cheminuclease activities, J. Mol. Struct., 1062, 147, 10.1016/j.molstruc.2014.01.026 Mahran, 2008, A-One Pot regioselective Synthesis of New Functionalized Derivatives of [1,2,4]triazolo[4,3-a]pyrimidin-5(1H)-one, Egypt. J. Chem., 52, 793 Shawali AS, Osman A. Synthesis and reactions of phenylcarbamoylarylhydrazidic chlorides, Tetrahedron, 1971;27(12): 2517-2528. Doi: 10.1016/S0040-4020(01)90753-7. Nemr, 2020, New fused pyrimidine derivatives with anticancer activity: Synthesis, topoisomerase II inhibition, apoptotic inducing activity and molecular modeling study, Bioorg. Chem., 103, 10.1016/j.bioorg.2020.104134 Cocco, 1985, Phytotoxic activity in pyrazole derivatives. II. Farmaco, Edizione, Scientifica, 40, 272 Mirzaei, 2020, Design, synthesis and biological evaluation of novel 5,6,7-trimethoxy-N-aryl-2-styrylquinolin-4-amines as potential anticancer agents and tubulin polymerization inhibitors, Bioorg. Chem., 98, 10.1016/j.bioorg.2020.103711 Hasanin, 2021, Synthesis of novel heterocyclic compounds based on dialdehyde cellulose: characterization, antimicrobial, antitumor activity, molecular dynamics simulation and target identification, Cellul., 28, 8355, 10.1007/s10570-021-04063-7 Pan, 2013, Molecular Dynamics Study of Zn(Aβ) and Zn(Aβ)2, PLoS One, 8, e70681, 10.1371/journal.pone.0070681 Wijffels, 2005, Conservation of Eubacterial Replicases, IUBMB Life, 57, 413, 10.1080/15216540500138246 Richmond, 1984, Solvent accessible surface area and excluded volume in proteins: Analytical equations for overlapping spheres and implications for the hydrophobic effect, J. Mol. Biol., 178, 63, 10.1016/0022-2836(84)90231-6 Sarker, 2007, Microtitre plate-based antibacterial assay incorporating resazurin as an indicator of cell growth, and its application in the in vitro antibacterial screening of phytochemicals, Methods, 42, 321, 10.1016/j.ymeth.2007.01.006 AbouAitah, 2021, Nanoformulation Composed of Ellagic Acid and Functionalized Zinc Oxide Nanoparticles Inactivates DNA and RNA Viruses, Pharmaceutics., 13, 2174, 10.3390/pharmaceutics13122174 Hersi, 2023, Discovery of novel papain-like protease inhibitors for potential treatment of COVID-19, Eur. J. Med. Chem., 254, 10.1016/j.ejmech.2023.115380 Ragab, 2022, Design, Synthesis, Antiviral Evaluation, and Molecular Dynamics Simulation Studies of New Spirocyclic Thiopyrimidinones as Anti HCoV-229E, Chem. Biodivers., 19, e202200632, 10.1002/cbdv.202200632 Pettersen, 2004, UCSF Chimera–a visualization system for exploratory research and analysis, J. Comput. Chem., 25, 1605, 10.1002/jcc.20084 Qiu, 2001, Refined structures of beta-ketoacyl-acyl carrier protein synthase III, J. Mol. Biol., 307, 341, 10.1006/jmbi.2000.4457 Zhang, 2020, Crystal structure of SARS-CoV-2 main protease provides a basis for design of improved α-ketoamide inhibitors, Science, 368, 409, 10.1126/science.abb3405 Li, 2005, Very fast empirical prediction and rationalization of protein pKa values, Proteins, 61, 704, 10.1002/prot.20660 Halford B. Reflections On ChemDraw. Chem Eng News Arch. 2014 Aug 18;92(33):26–7. Hanwell, 2012, Avogadro: an advanced semantic chemical editor, visualization, and analysis platform, J Cheminform, 4, 17, 10.1186/1758-2946-4-17 Hospital, 2015, Molecular dynamics simulations: advances and applications, Adv Appl Bioinform Chem., 8, 37 Wang, 2006, Automatic atom type and bond type perception in molecular mechanical calculations, J. Mol. Graph. Model., 25, 247, 10.1016/j.jmgm.2005.12.005 Roe, 2013, PTRAJ and CPPTRAJ: Software for Processing and Analysis of Molecular Dynamics Trajectory Data, J Chem Theory Comput [internet]., 9, 3084, 10.1021/ct400341p Pettersen, 2004, UCSF Chimera–a visualization system for exploratory research and analysis, J. Comput. Chem., 25, 1605, 10.1002/jcc.20084 Seifert, 2014, OriginPro 9.1: Scientific data analysis and graphing software - Software review, J. Chem. Inf. Model., 54, 1552, 10.1021/ci500161d