【病毒外文文献】2018 Synthesis, biological evaluation and molecular modeling of a novel series of fused 1,2,3-triazoles as potential ant

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Accepted Manuscript Synthesis biological evaluation and molecular modeling of a novel series of fused 1 2 3 triazoles as potential anti coronavirus agents Konstantina Karypidou Sergio R Ribone Mario A Quevedo Leentje Persoons Christophe Pannecouque Christine Helsen Frank Claessens Wim Dehaen PII S0960 894X 18 30750 9 DOI https doi org 10 1016 j bmcl 2018 09 019 Reference BMCL 26040 To appear in Bioorganic 767 769 23 2 Drosten C G nther S Preiser W Van der Werf S Brodt HR Becker S Rabenau H Panning M 24 Kolesnikova L Fouchier RAM Berger A Burgui re AM Cinatl J Eickmann M Escriou N Grywna K 25 Kramme S Manuguerra JC M ller S Rickerts V St rmer M Vieth S Klenk HD Osterhaus ADME 26 Schmitz H Doerr HW Identification of a novel coronavirus in patients with severe acute respiratory 27 syndrome N Engl J Med 2003 348 1967 1976 DOI https doi org 10 1056 NEJMoa030747 28 3 Kuiken T Fouchier RAM Schutten M Rimmelzwaan GF Van Amerongen G Van Riel D Laman JD De 29 Jong T Van Doornum G Lim W Ling AE Chan PKS Tam JS Zambon MC Gopal R Drosten C Van 30 der Werf S Escriou N Manuguerra JC St hr K Peiris JSM Osterhaus ADME Newly discovered 31 coronavirus as the primary cause of severe acute respiratory syndrome Lancet 2003 362 263 270 32 https doi org 10 1016 S0140 6736 03 13967 0 33 4 Communicable Disease Surveillance and response WHO SARS case fatality ratio incubation period 34 http www who int csr sars archive 2003 05 07a en Published 7 May 2003 35 5 Van Der Hoek L Pyrc K Jebbink MF Vermeulen Oost W Berkhout RJM Wolthers KC Wertheim van 36 Dillen PME Kaandorp J Spaargaren J Berkhout B Identification of a new human coronavirus Nat 37 Med 2004 10 368 373 https doi org 10 1038 nm1024 38 6 Woo PCY Lau SKP Chu C Chan K Tsoi H Huang Y Wong BHL Poon RWS Cai JJ Luk W Poon 39 LLM Wong SSY Guan Y Peiris JSM Yuen K Characterization and Complete Genome Sequence of a 40 Novel Coronavirus Coronavirus HKU1 from Patients with Pneumonia J Virol 2005 79 884 895 41 https doi org 10 1128 JVI 79 2 884 895 2005 1 7 Zaki AM Van Boheemen S Bestebroer TM Osterhaus ADME Fouchier RAM Isolation of a Novel 2 Coronavirus from a Man with Pneumonia in Saudi Arabia N Engl J Med 2012 367 1814 1820 3 https doi org 10 1056 NEJMoa1211721 4 8 Chan JFW Lau SKP To KKW Cheng VCC Woo PCY Yuen KY Middle East Respiratory syndrome 5 coronavirus Another zoonotic betacoronavirus causing SARS like disease Clin Microbiol Rev 2015 6 28 465 522 https doi org 10 1128 CMR 00102 14 7 9 Zumla A Chan JFW Azhar EI Hui DSC Yuen KY Coronaviruses drug discovery and therapeutic 8 options Nat Rev Drug Discov 2016 15 327 347 https doi org 10 1038 nrd 2015 37 9 10 Pillaiyar T Manickam M Namasivayam V Hayashi Y Jung SH An overview of severe acute 10 respiratory syndrome coronavirus SARS CoV 3CL protease inhibitors Peptidomimetics and small 11 molecule chemotherapy J Med Chem 2016 59 6595 6628 12 https doi org 10 1021 acs jmedchem 5b01461 13 11 Anand K Ziebuhr J Wadhwani P Mesters JR Hilgenfeld R Coronavirus Main Proteinase 3CL pro 14 Structure Basis for Design of Anti SARS Drugs Science 2003 300 15 1763 1767 https doi org 10 1126 science 1085658 16 12 Thomas J Jana S John J Liekens S Dehaen W A general metal free route towards the synthesis of 17 1 2 3 triazoles from readily available primary amines and ketones Chem Commun 2016 52 2885 18 2888 https doi org 10 1039 c5cc08347h 19 13 Yang S Chen SJ Hsu MF Wu JD Tseng CTK Liu YF Chen HC Kuo CW Wu CS Chang LW Chen 20 WC Liao SY Chang TY Hung HH Shr HL Liu CY Huang YA Chang LY Hsu JC Peters CJ Wang 21 AHJ Hsu MC Synthesis crystal structure structure activity relationships and antiviral activity of a 22 potent SARS coronavirus 3CL protease inhibitor J Med Chem 2006 49 4971 4980 https doi org 23 10 1021 jm0603926 24 14 Chen LR Wang YC Lin YW Chou SY Chen SF Liu LT Wu YT Kuo CJ Chen TSS Juang SH 25 Synthesis and evaluation of isatin derivatives as effective SARS coronavirus 3CL protease inhibitors 26 Bioorg Med Chem Lett 2005 15 3058 3062 https doi org 10 1016 j bmcl 2005 04 027 27 15 Wu CY King KY Kuo CJ Fang JM Wu YT Ho MY Liao CL Shie JJ Liang PH Wong CH Stable 28 Benzotriazole Esters as Mechanism Based Inactivators of the Severe Acute Respiratory Syndrome 3CL 29 Protease Chem Biol 2006 13 261 268 https doi org 10 1016 j chembiol 2005 12 008 30 16 Ghosh AK Gong G Grum Tokars V Mulhearn DC Baker SC Coughlin M Prabhakar BS Sleeman K 31 Johnson ME Mesecar AD Design synthesis and antiviral efficacy of a series of potent chloropyridyl 32 ester derived SARS CoV 3CLpro inhibitors Bioorg Med Chem Lett 2008 18 5684 5688 33 https doi org 10 1016 j bmcl 2008 08 082 34 17 Zhang J Huitema C Niu C Yin J James MNG Eltis LD Vederas JC Aryl methylene ketones and 35 fluorinated methylene ketones as reversible inhibitors for severe acute respiratory syndrome SARS 36 3Clike proteinase Bioorg Chem 2008 36 229 240 https doi org 10 1016 j bioorg 2008 01 001 37 18 Jacobs J Grum Tokars V Zhou Y Turlington M Saldanha SA Chase P Eggler A Dawson ES 38 BaezSantos YM Tomar S Mielech AM Baker SC Lindsley CW Hodder P Mesecar A Stauffer SR 39 Discovery synthesis and structure based optimization of a series of N tert Butyl 2 N arylamido 40 2 pyridin 3 yl acetamides ML188 as potent noncovalent small molecule inhibitors of the severe acute 41 respiratory syndrome coronavirus SARS CoV 3CL J Med Chem 2013 56 534 546 42 https doi org 10 1021 jm301580n 43 19 Turlington M Chun A Tomar S Eggler A Grum Tokars V Jacobs J Daniels JS Dawson E Saldanha 44 A Chase P Baez Santos YM Lindsley CW Hodder P Mesecar AD Stauffer SR Discovery of 45 N benzo 1 2 3 triazol 1 yl N benzyl acetamido phenyl carboxamides as severe acute respiratory 46 syndrome coronavirus SARS CoV 3CLpro inhibitors Identification of ML300 and noncovalent 47 nanomolar inhibitors with an induced fit binding Bioorg Med Chem Lett 2013 23 6172 6177 48 http doi org 10 1016 j bmcl 2013 08 112 1 20 Gallagher MJ Mann FG The structure and properties of certain polycyclic indolo and 2 quinolinoderivatives Part XV Derivatives of 1 phenyl 4 piperidone and its phosphorus and arsenic 3 analogues J Chem Soc 1962 23 5110 4 21 Sch n U Messinger J Buckendahl M Prabhu MS Konda A An improved synthesis of N aryl and 5 Nheteroaryl substituted piperidones Tetrahedron Lett 2007 48 2519 2525 6 http doi org 10 1016 j tetlet 2007 02 053
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