Recent advances in the discovery and synthesis of neuraminidase inhibitors

Bibliography

• SERVICE RF: Researchers seek new weapon against the flu. Science (1997) 275:756–757.
   PubMed Web of Science ®Google Scholar
• GIEZEN WP: Serious morbidity and mortality associated with influenza epidemics. Epidemiol. Rev. (1982) 4:25–44.
   PubMed Web of Science ®Google Scholar
• •A review of the epidemiology of influenza.
   Google Scholar
• NICHOLSON KG: Impact of influenza and respiratory syncytial virus on mortality in England and Wales from January 1975 to December 1990. Epidemiol. Infic. (1996) 116:51–63.
   PubMed Web of Science ®Google Scholar
• FISCHETTI M: Preparing for battle. Sci. Am. (2001) 284:82–83.
   Web of Science ®Google Scholar
• WEBSTER RG: Influenza: an emerging disease. Emerg-. Infect. Dis. (1998) 4(3).
   Web of Science ®Google Scholar
• HILEMAN B: preparing for avian flu. Chem. Eng. News (April 4, 2005):47–52.
   Google Scholar
• GOVORKOVA EA, REHG JE, KRAUSS S et al.: Lethality to ferrets of H5N1 influenza viruses isolated from humans and poultry in 2004.1 Virol. (2005) 79:2191–2198.
   Google Scholar
• CDC: Recent avian influenza outbreaks in Asia. CDC-influenza (Flu)/recent outbreaks in Asia (19 May 2005).
   Google Scholar
• WOOD JM: Standardization of inactivated influenza vaccines. In: Textbook ofInfluenza. Nicholson KG, Webster RG, Hay AJ (Eds), Oxford, UK (1990333–345.
   Google Scholar
• CDC: Delayed supply of influenza vaccine and adjunct ACIP influenza vaccine recommendations for the 2000-01 influenza season. Advisory Committee on Immunization Practices. MMWR Morb. Mortal. Wkly. Rep. (2000) 49:619–622.
   PubMedGoogle Scholar
• WANG GT: Recent advances in the discovery and development of anti-influenza drugs. Expert Opin. Ther. Patents (2002) 12(6):845–861.
   Web of Science ®Google Scholar
• •Previous review article on the same topic.
   Google Scholar
• Orthomyxoviridae: the viruses and their replication. In: Fields' Virology, Fourth Edition. Knipe DM, Howley PM (Eck), Lippincott Williams & Wilkins, Philadelphia (2001).
   Google Scholar
• STIVER G: The treatment of influenza with antiviral drugs. CMAJ (2003) 168(1):49–56.
   PubMed Web of Science ®Google Scholar
• McKIMM-BRESCHKIN JL: Neuraminidase inhibitors for the treatment and prevention of influenza. Expert Opin. Pharmacother. (2002) 3(2):103–112.
   PubMedGoogle Scholar
• DE CLERCQ E. Strategies in the design of antiviral drugs. Nat. Rev. Drug Discov. (2002) 1(1):13–25.
   PubMed Web of Science ®Google Scholar
• MEINDL P, BODO G, PALESE P et al.: Inhibition of neuraminidase activity by derivatives of 2-deoxy-2,3-dehydro-N-acetylneuraminic acid. Virology (1974) 58:457–463.
   PubMed Web of Science ®Google Scholar
• PALESE P, COMPANS RW: Inhibition of influenza virus replication in tissue culture by 2-deoxy-2,3 dehydro-N-trifluoroacetylneuraminic acid (FANA): mechanism of action. J. Gen. Wrol. (1976) 33:139–163.
   Google Scholar
• PALESE P, SCHULMAN JL, BODO G et al.: Inhibition of influenza and parainfluenza virus replication in tissue culture by 2-deoxy-2,3 dehydro-N-trifluoroacetylneuraminic acid (FANA). Virology (1974) 59:490–498.
   PubMed Web of Science ®Google Scholar
• COLMAN PM, VARGHESE JN, LAVER WG: Structure of the catalytic and antigenic sites in influenza virus neuraminidase. Nature (1983) 303:41–44.
   PubMed Web of Science ®Google Scholar
• •One of the first two papers on the X-ray crystallographic structure of influenza NA.
   Google Scholar
• VARGHESE JN, LAVER WG, COLMAN PM: Structure of the influenza virus glycoprotein antigen neuraminidase at 2.9 A resolution. Nature (1983) 303:35–40.
   PubMed Web of Science ®Google Scholar
• •One of the first two papers on the X-ray crystallographic structure of influenza NA.
   Google Scholar
• BURMEISTER WP, RUIGROK RW, CUSACK S: The 2.2 A resolution crystal structure of influenza B neuraminidase and its complex with sialic acid. EMBO J. (1992) 11:49–56.
   Google Scholar
• VARGHESE JN, EPA VC, COLMAN PM:Three-dimensional structure of the complex of 4-guanidino-Neu5Ac2en and influenza virus neuraminidase. Protein Sci. (1995) 4:1081–1087.
   PubMed Web of Science ®Google Scholar
• •X-ray crystallographic structure of influenza NA complexed to zanamivir.
   Google Scholar
• TAYLOR NR, CLEASBY A. SINGH 0 et al.: Dihydropyrancarboxamides related to zanamivir: A new class of inhibitors of influenza virus sialidase. 2. Crystallographic and molecular modeling study of complex of 4-amino-4H-pyran-6-carboxamides and sialidase from influenza virus A and B. 1 Med. Chem. (1998) 41:798–807.
   Google Scholar
• •X-ray crystallographic studies of the amide analogues of zanamivir (GlaxoSmithKline).
   Google Scholar
• ITZSTEIN MV, WU W-Y, KOK GB et al.: Rational design of potent sialidase-based inhibitors of influenza virus replication. Nature (1993) 363:418–423.
   PubMed Web of Science ®Google Scholar
• •Design and properties of zanamivir.
   Google Scholar
• COLACINO JM, STASCHKE KA, LAVER WG: Approaches and strategies for the treatment of influenza virus infections. Antiviral Chem. Chemother. (1999) 10:155–185.
   PubMed Web of Science ®Google Scholar
• •A recent review of anti-influenza therapy.
   Google Scholar
• KIM CU, CHEN X, MENDEL DB: Neuraminidase inhibitors as anti-influenza virus agents. Antiviral Chem. Chemother. (1999) 10:141–154.
   PubMed Web of Science ®Google Scholar
• •A recent review of NA inhibition.
   Google Scholar
• GRAVENSTEIN S, JOHNSTON SL, LOESCHEL E et al.: Zanamivir: a review of clinical safety in individuals at high risk of developing influenza-related complications. Drug Saf (2001) 24(15):1113–1125.
   PubMed Web of Science ®Google Scholar
• DRINNAN NB, VARI F: Aspects of the stability and bioavailability of carbohydrates and carbohydrate derivatives. Mini Rev. Med. Chem. (2003) 3(7):633–649.
   PubMed Web of Science ®Google Scholar
• MACDONALD SJF, CAMERON R, DEMAINE DA et al.: Dimeric zanamivir conjugates with various linking groups are potent, long-lasting inhibitors of influenza neuraminidase including H5N1 avian influenza. 1 Med. Chem. (2005) 48:2964–2971.
   Google Scholar
• HAYDEN FG, TREANOR JJ, SCOTT FRet al.: Use of the oral neuraminidase inhibitor oseltamivir in experimental human influenza: randomized controlled trials for prevention and treatment. J. Am. Med. Assoc. (1999) 282:1240–1246.
   Google Scholar
• •Results of the clinical trials of oseltamivir.
   Google Scholar
• HAYDEN FG, ATMAR RL, MARGO S et al.: Use of the selective oral neuraminidase inhibitor oseltamivir to prevent influenza. N Engl. J. Med. (1999) 341:1336–1343.
   PubMed Web of Science ®Google Scholar
• •Results of the clinical trials of oseltamivir.
   Google Scholar
• TREANOR JJ, HAYDEN FG, VROOMAN PS et al.: Efficacy and safety of the oral neuraminidase inhibitor oseltamivir in treating acute influenza: a randomized controlled trial. /AMA (2000) 283:1016–1024.
   PubMed Web of Science ®Google Scholar
• •Results of the clinical trials of oseltamivir.
   Google Scholar
• HAYDEN FG, JENNINGS L, ROBSON R et al.: Oral oseltamivir in human experimental influenza B infection. Antiviral Ther. (2000) 5:205–213.
   PubMed Web of Science ®Google Scholar
• •Results of the clinical trials of oseltamivir.
   Google Scholar
• BABU YS, CHAND P, BANTIA S et al.: BCX-1812 (RWJ-270201): Discovery of a novel, highly potent, orally active, and selective influenza neuraminidase inhibitor through structure-based drug design. J. Med. Chem. (2000) 43:3482–3486.
   PubMed Web of Science ®Google Scholar
• CHAND P, KOTIAN PL, DEHGHANI A et al.: Systematic structure-based design and stereoselective synthesis of novel multisubstituted cyclopentane derivatives with potent antiinfluenza activity. J. Med. Chem. (2001) 44:4379–4392.
   PubMed Web of Science ®Google Scholar
• •Synthesis of BCX-1812.
   Google Scholar
• CHAND P, BABU YS, BANTIA S et al.: Syntheses and neuraminidase inhibitory activity of multisubstituted cyclopentane amide derivatives. J. Med. Chem. (2004) 47:1919–1929.
   PubMed Web of Science ®Google Scholar
• BANTIA S, PARKER CD, ANANTH SL et al.: Comparison of the anti-influenza virus activity of RWJ-270201 with those of oseltamivir and zanamivir. Antimicrob. Agents Chemother. (2001) 45:1162–1167.
   PubMed Web of Science ®Google Scholar
• SMEE DF, HUFFMAN JH, MORRISON AC et al.: Cyclopentane neuraminidase inhibitors with potent in vitro anti-influenza virus activities. Antimicrob. Agents Chemother. (2001) 45:743–748.
   PubMed Web of Science ®Google Scholar
• CHAND P, BANTIA S, KOTIAN PL et al: Comparison of the anti-influenza virus activity of cyclopentane derivatives with oseltamivir and zanamivir in vivo. Bioorg Med. Chem. (2005) 13:4071–4077.
   PubMed Web of Science ®Google Scholar
• SWEET C, JAKEMAN KJ, BUSH K et al.: Oral administration of cyclopentane neuraminidase inhibitors protects ferrets against influenza virus infection. Antimicrob. Agents Chemother. (2002) 46:996–1004.
   PubMed Web of Science ®Google Scholar
• GOVORKOVA FA, LENEVA IA, GOLOUBEVA, OG et al.: Comparison of efficacies of RWJ-270201, zanamivir, and oseltamivir against H5N1, H9N2, and other avian influenza viruses. Antimicrob. Agents Chemother. (2001) 45:2723–2732.
   PubMed Web of Science ®Google Scholar
• GUBAREVA LV, WEBSTER RG, HAYDEN FG: Comparison of the activities of zanamivir, oseltamivir, and RWJ-270201 against clinical isolates of influenza virus and neuraminidase inhibitor-resistant variants. Antimicrob. Agents Chemother. (2001) 45:3403–3408.
   PubMed Web of Science ®Google Scholar
• STEWART K: Structure-based discovery ofnovel influenza neuraminidase inhibitors. Antimicrobial and Antiviral Drug Discovery Conference. Boston, MA, USA (17 August 2001).
   Google Scholar
• KATI W, MONTGOMERY D, CARRICK R et al.: In vitro characterization of A-315675, a highly potent inhibitor of A and B strain influenza virus neuraminidase and influenza replication. Antimicrob. Agents Chemother. (2002) 46:1014–1021.
   PubMed Web of Science ®Google Scholar
• VON ITZSTEIN M, WU W-Y, JIN B: The synthesis of 2,3-didehydro-2,4-dideoxy-4-guanidinyl-N-acetylneuraminic acid: a potent influenza virus sialiciase inhibitor. Carbohydr. Res. (1994) 259:301–305.
   PubMed Web of Science ®Google Scholar
• •First synthesis of zanamivir.
   Google Scholar
• ABDEL-MAGID AF, MARYANOFF CA, MEHRMAN SJ: Synthesis of influenza neuraminidase inhibitors. Curr. Opin. Drug Discov. Dev. (2001) 4:776–791.
   PubMedGoogle Scholar
• CHANDLER M, BAMFORD MJ, CONROY R et al.: Synthesis of the potent influenza neuraminidase inhibitor 4-guanidino Neu5Ac2en. X-ray molecular structure of 5-acetamido-4-amino-2,6-anhydro-3,4,5-trideoxy-D-erythro-L-gluco-nonionic acid. J. Chem. Soc. Perkin Trans. 1 (1995) 9:1173-1180.
   Google Scholar
• KIM CU, LEW W, WILLIAMS MA et al.:Influenza neuraminidase inhibitors possessing a novel hydrophobic interaction in the enzyme active site: design, synthesis, and structural analysis of carbocyclic sialic acid analogs with potent anti-influenza activity. J. Am. Chem. Soc. (1997) 119:681–690.
   PubMed Web of Science ®Google Scholar
• ROHLOFF JC, KENT KM, POSTICH MJ et al.: Practical total synthesis of the anti-influenza drug GS-4104.J. Org. Chem. (1998) 63:4545–4550.
   Google Scholar
• FEDERSPIEL M, FISCHER R, HENNIG M et al.: Industrial synthesis of the key precursor in the synthesis of the anti-influenza drug oseltamivir phosphate (Ro 64-0796/002, GS-4104-02): Ethyl (3R,45,55)-4,5-epoxy-3-(1-ethyl-propoxy)-1-cyclohex-1-ene-1-carboxylate. Org. Process Res. Dev. (1999) 3:266–274.
   Web of Science ®Google Scholar
• KARPF M, TRUSSARDI R: New, azide-free transformation of epoxides into 1,2-diamino compounds: synthesis of the anti-influenza neuraminidase inhibitor oseltamivir phosphate (Tamiflu). J. Org. Chem. (2001) 66:2044–2051.
   PubMed Web of Science ®Google Scholar
• DEGOEY DA, CHEN H-J, FLOSI WJ et al.: Enantioselective synthesis of antiinfluenza compound A-315675. J. Org. Chem. (2002) 67:5445–5453.
   PubMed Web of Science ®Google Scholar