Design, synthesis and anti-HBV activity evaluation of new substituted imidazo[4,5-b]pyridines

Bioorganic Chemistry - Tập 98 - Trang 103580 - 2020
Maria Gerasi1, Efseveia Frakolaki2, Georgios Papadakis1, Anna Chalari2, Nikolaos Lougiakis1, Panagiotis Marakos1, Nicole Pouli1, Niki Vassilaki2
1Division of Pharmaceutical Chemistry, Department of Pharmacy, National and Kapodistrian University of Athens, Panepistimiopolis-Zografou, Athens 15771, Greece
2Molecular Virology Laboratory, Hellenic Pasteur Institute, 127 Vas. Sofias ave., 11521 Athens, Greece

Tài liệu tham khảo

MacLachlan, 2015, Hepatitis B virus epidemiology, Cold Spring Harb Perspect Med, 5, a021410, 10.1101/cshperspect.a021410 Hepatitis B, World Health Organization 2018: 2019). https://www.who.int/news-room/fact-sheets/detail/hepatitis-b. Lin, 2015, Hepatitis B virus genotypes and variants, Cold Spring Harb. Perspect. Med., 5, a021436, 10.1101/cshperspect.a021436 Lau, 1993, Molecular virology and pathogenesis of hepatitis B, Lancet, 342, 1335, 10.1016/0140-6736(93)92249-S Venkatakrishnan, 2016, The structural biology of hepatitis B Virus: form and function, Annu. Rev. Virol., 3, 429, 10.1146/annurev-virology-110615-042238 Tu, 2017, HBV DNA integration molecular mechanisms and clinical implications, Viruses, 9, 75, 10.3390/v9040075 Hu, 2015, Hepadnavirus genome replication and persistence, Cold Spring Harbor Perspect. Med., 5, a021386, 10.1101/cshperspect.a021386 Clark, 2015, Unveiling the roles of HBV polymerase for new antiviral strategies, Future Virol., 10, 283, 10.2217/fvl.14.113 Basagoudanavar, 2006, Regulation of hepadnavirus reverse transcription by dynamic nucleocapsid phosphorylation, J. Virol., 81, 1641, 10.1128/JVI.01671-06 Blondot, 2016, Intracellular transport and egress of hepatitis B virus, J. Hepatol., 64, S49, 10.1016/j.jhep.2016.02.008 Lentz, 2011, Roles of the envelope proteins in the amplification of covalently closed circular DNA and completion of synthesis of the plus-strand DNA in hepatitis B virus, J. Virol., 85, 11916, 10.1128/JVI.05373-11 Siddiqui, 2019, DNA Polymerase alpha is essential for intracellular amplification of hepatitis B virus covalently closed circular DNA, PLoS Pathog., 15, e1007742, 10.1371/journal.ppat.1007742 Lee, 2019, Updates on chronic HBV: current challenges and future goals, Curr. Treat Opt. Gastroenterol., 17, 271, 10.1007/s11938-019-00236-3 Konerman, 2016, Interferon treatment for hepatitis B, Clin. Liver Dis., 20, 645, 10.1016/j.cld.2016.06.002 E.E.E. European Association for the Study of the Liver. Electronic address, L. European Association for the Study of the, EASL 2017 Clinical Practice Guidelines on the management of hepatitis B virus infection, Journal of hepatology 67(2) (2017) 370-398. Terrault, 2018, Update on prevention, diagnosis, and treatment of chronic hepatitis B: AASLD 2018 hepatitis B guidance, Hepatology, 67, 1560, 10.1002/hep.29800 Rivkin, 2005, A review of entecavir in the treatment of chronic hepatitis B infection, Curr. Med. Res. Opin., 21, 1845, 10.1185/030079905X65268 Clark, 2015, Hepatitis B virus reverse transcriptase - Target of current antiviral therapy and future drug development, Antiviral Res., 123, 132, 10.1016/j.antiviral.2015.09.011 Yeo, 2019, Factors associated with rates of HBsAg seroclearance in adults with chronic HBV Infection: a systematic review and meta-analysis, Gastroenterology, 156, 10.1053/j.gastro.2018.10.027 Yang, 2014, Persistence of hepatitis B virus covalently closed circular DNA in hepatocytes: molecular mechanisms and clinical significance, Emerging Microbes Infect., 3, e64 Mak, 2019, Novel developments of hepatitis B: treatment goals, agents and monitoring tools, Expert Rev. Clin. Pharmacol., 12, 109, 10.1080/17512433.2019.1567327 Painter, 2007, Evaluation of hexadecyloxypropyl-9-R-[2-(Phosphonomethoxy)propyl]- adenine, CMX157, as a potential treatment for human immunodeficiency virus type 1 and hepatitis B virus infections, Antimicrob. Agents Chemother., 51, 3505, 10.1128/AAC.00460-07 Wedemeyer, 2018, Final results of a multicenter, open-label phase 2b clinical trial to assess safety and efficacy of Myrcludex B in combination with Tenofovir in patients with chronic HBV/HDV co-infection, J. Hepatol., 68, 10.1016/S0168-8278(18)30224-1 Gish, 2015, Synthetic RNAi triggers and their use in chronic hepatitis B therapies with curative intent, Antiviral Res., 121, 97, 10.1016/j.antiviral.2015.06.019 Mak, 2017, Hepatitis B core protein as a therapeutic target, Expert Opin Ther Targets, 21, 1153, 10.1080/14728222.2017.1397134 Mohebbi, 2018, An overview of hepatitis B virus surface antigen secretion inhibitors, Front. Microbiol., 9, 662, 10.3389/fmicb.2018.00662 Zhang, 2014, A review of non-nucleoside anti-hepatitis B virus agents, Eur. J. Med. Chem., 75, 267, 10.1016/j.ejmech.2014.01.046 Pei, 2017, Past, current, and future developments of therapeutic agents for treatment of chronic hepatitis B virus infection, J. Med. Chem., 60, 6461, 10.1021/acs.jmedchem.6b01442 Li, 2006, Synthesis and anti-hepatitis B virus activity of novel benzimidazole derivatives, J. Med. Chem., 49, 4790, 10.1021/jm060330f Akhtar, 2017, Therapeutic evolution of benzimidazole derivatives in the last quinquennial period, Eur. J. Med. Chem., 126, 705, 10.1016/j.ejmech.2016.12.010 Tonelli, 2014, Antiviral activity of benzimidazole derivatives. III. novel anti-CVB-5, anti-RSV and anti-Sb-1 agents, Bioorg. Med. Chem., 22, 4893, 10.1016/j.bmc.2014.06.043 Luo, 2010, Design and synthesis of novel benzimidazole derivatives as inhibitors of hepatitis B virus, Bioorg. Med. Chem., 18, 5048, 10.1016/j.bmc.2010.05.076 Li, 2007, Identification of 1-isopropylsulfonyl-2-amine benzimidazoles as a new class of inhibitors of hepatitis B virus, Eur. J. Med. Chem., 42, 1358, 10.1016/j.ejmech.2007.03.005 Xu, 2014, Benzimidazole derivative, BM601, a novel inhibitor of hepatitis B virus and HBsAg secretion, Antiviral Res., 107, 6, 10.1016/j.antiviral.2014.04.002 Wang, 2016, Recent developments in antivirals against hepatitis B virus, Virus Res., 213, 205, 10.1016/j.virusres.2015.12.014 Lougiakis, 2017, Novel nucleoside analogues targeting HCV replication through an NS5A-dependent inhibition mechanism, Chem. Biol. Drug Des., 90, 352, 10.1111/cbdd.12966 Lougiakis, 2016, Design and synthesis of purine analogues as highly specific ligands for FcyB, a ubiquitous fungal nucleobase transporter, Bioorg. Med. Chem., 24, 5941, 10.1016/j.bmc.2016.09.055 Michailidou, 2016, Novel pyrazolopyridine derivatives as potential angiogenesis inhibitors: Synthesis, biological evaluation and transcriptome-based mechanistic analysis, Eur. J. Med. Chem., 121, 143, 10.1016/j.ejmech.2016.05.035 Ding, 2012, Convenient and practical synthesis of 6-chloro-2-(chloromethyl)-thiazolo[5,4-B]pyridine, Synth. Commun., 42, 2791, 10.1080/00397911.2011.566408 Turner, 1983, Regiospecific electrophilic substitution of aminopyridines - ortho lithiation of 2, 3, and 4-(pivaloylamino) pyridines, J. Org. Chem., 48, 3401, 10.1021/jo00168a007 Kettle, 2012, Diverse heterocyclic scaffolds as allosteric inhibitors of AKT, J. Med. Chem., 55, 1261, 10.1021/jm201394e Micheli, 1997, 2,3-Dihydro-6,7-dichloro-pyrido[2,3-b]pyrazine-8-oxide as selective glycine antagonist with in vivo activity, Bioorg. Med. Chem., 5, 2129, 10.1016/S0968-0896(97)00156-9 Feng, 2018, Discovery of MK-8722: a systemic direct pan-activator of AMP-activated protein kinase, ACS Med. Chem. Lett., 9, 39, 10.1021/acsmedchemlett.7b00417 Ladner, 1997, Inducible expression of human hepatitis B virus (HBV) in stably transfected hepatoblastoma cells: a novel system for screening potential inhibitors of HBV replication, Antimicrob. Agents Chemother., 41, 1715, 10.1128/AAC.41.8.1715 Ni, 2014, Hepatitis B and D viruses exploit sodium taurocholate co-transporting polypeptide for species-specific entry into hepatocytes, Gastroenterology, 146, 1070, 10.1053/j.gastro.2013.12.024 Delaney, 2006, Intracellular metabolism and in vitro activity of tenofovir against hepatitis B virus, Antimicrob. Agents Chemother., 50, 2471, 10.1128/AAC.00138-06 Cihlar, 2002, Tenofovir exhibits low cytotoxicity in various human cell types: comparison with other nucleoside reverse transcriptase inhibitors, Antiviral Res., 54, 37, 10.1016/S0166-3542(01)00210-8 Tan, 2018, When hepatitis B virus meets interferons, Front. Microbiol., 9, 10.3389/fmicb.2018.01611 Tsuge, 2017, Development of a novel site-specific pegylated interferon beta for antiviral therapy of chronic hepatitis B virus, Antimicrob. Agents Chemother., 61, 10.1128/AAC.00183-17 Liu, 2015, The Efficacy and safety of entecavir and interferon combination therapy for chronic hepatitis B virus infection: a meta-analysis, PLoS ONE, 10, e0132219, 10.1371/journal.pone.0132219 Seitz, 2016, A slow maturation process renders hepatitis B virus infectious, Cell Host Microbe., 20, 25, 10.1016/j.chom.2016.05.013 Scaglioni, 1997, Posttranscriptional regulation of hepatitis B virus replication by the precore protein, J. Virol., 71, 345, 10.1128/JVI.71.1.345-353.1997 Cai, 2012, Identification of disubstituted sulfonamide compounds as specific inhibitors of hepatitis B virus covalently closed circular DNA formation, Antimicrob. Agents Chemother., 56, 4277, 10.1128/AAC.00473-12