Design, synthesis, and biological evaluation of crenatoside analogues as novel influenza neuraminidase inhibitors

European Journal of Medicinal Chemistry

Volumn 109, Issue , 2016, Pages 199-205

  Chen, Bao Long ^a   Wang, Ya Jing ^b   Guo, Hong ^a   Zeng, Guang Yao ^a  

^a CENTRAL SOUTH UNIVERSITY   (China)

^b HUNAN UNIVERSITY OF CHINESE MEDICINE   (China)

Author keywords

Crenatoside derivatives; Design; Influenza virus; Neuraminidases inhibitors; Synthesis

Indexed keywords

CRENATOSIDE; CRENATOSIDE DERIVATIVE; GLYCOSIDE; ISOCRENATOSIDE; NATURAL PRODUCT; SIALIDASE INHIBITOR; UNCLASSIFIED DRUG; ANTIVIRUS AGENT; CAFFEIC ACID DERIVATIVE; ENZYME INHIBITOR; GLUCOSIDE; SIALIDASE;

ANTIVIRAL ACTIVITY; ARTICLE; BIOLOGICAL ACTIVITY; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; IC50; INFLUENZA VIRUS; NONHUMAN; POGOSTEMON CABLIN; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; ANTAGONISTS AND INHIBITORS; CHEMISTRY; DRUG EFFECTS; ENZYMOLOGY; HUMAN; INFLUENZA A VIRUS; INFLUENZA A VIRUS (H1N1); INFLUENZA, HUMAN; METABOLISM; MOLECULAR MODEL; STRUCTURE ACTIVITY RELATION; VIROLOGY;

ANTIVIRAL AGENTS; CAFFEIC ACIDS; DRUG DESIGN; ENZYME INHIBITORS; GLUCOSIDES; HUMANS; INFLUENZA A VIRUS; INFLUENZA A VIRUS, H1N1 SUBTYPE; INFLUENZA, HUMAN; MODELS, MOLECULAR; NEURAMINIDASE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84954045279     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2015.12.031     Document Type: Article

References (17)

1. R. Salomon, and R.G. Webster The influenza virus enigma Cell 136 3 2009 402 410
2. J. An, D.C.W. Lee, A.H.Y. Law, C.L.H. Yang, L.L.M. Poon, A.S.Y. Lau, and S.J.M. Jones A novel small-molecule inhibitor of the avian influenza H5N1 virus determined through computational screening against the neuraminidase J. Med. Chem. 52 9 2009 2667 2672
3. W. Fiers, M. De Filette, A. Birkett, S. Neirynck, and W. Min Jou A "universal" human influenza A vaccine Virus Res. 103 1-2 2004 173 176
4. M.I. Lin, B.H. Su, C.H. Lee, S.T. Wang, W.C. Wu, P. Dangate, S.Y. Wang, W.I. Huang, T.J. Cheng, O.A. Lin, Y.S. Cheng, Y.J. Tseng, and C.M. Sun Synthesis and inhibitory effects of novel pyrimido-pyrrolo-quinoxalinedione analogues targeting nucleoproteins of influenza A virus H1N1 Eur. J. Med. Chem. 102 2015 477 486
5. S. Niu, L. Si, D. Liu, A. Zhou, Z. Zhang, Z. Shao, S. Wang, L. Zhang, D. Zhou, and W. Lin Spiromastilactones: a new class of influenza virus inhibitors from deep-sea fungus Eur. J. Med. Chem. 108 2016 229 244
6. A.S. Sokolova, O.I. Yarovaya, A.V. Shernyukov, Y.V. Gatilov, Y.V. Razumova, V.V. Zarubaev, T.S. Tretiak, A.G. Pokrovsky, O.I. Kiselev, and N.F. Salakhutdinov Discovery of a new class of antiviral compounds: camphor imine derivatives Eur. J. Med. Chem. 105 2015 263 273
7. M.N. Matrosovich, T.Y. M, T. Gray, N.A. Roberts, and H.D. Klenk Neuraminidase is important for the initiation of influenza virus infection in human airway epithelium J. Virol. 78 2004 12665 12667
8. A. Moscona Global transmission of oseltamivir-resistant influenza N. Engl. J. Med. 360 2009 953 956
9. D.J. Newman, and G.M. Cragg Natural products as sources of new drugs over the 30 years from 1981 to 2010 J. Nat. Prod. 75 3 2012 311 335
10. J. Clardy, and C. Walsh Lessons from natural molecules Nature 432 2004 829 837
11. Z. Zhao, J. Lu, K. Leung, C.L. Chan, and Z.-H. Jiang Determination of patchoulic alcohol in herba pogostemonis by GC-MS-MS Chem. Pharm. Bull. 53 7 2005 856 860
12. X.-F. Luo, F. Lei, Y. He, S.-C. Pei, L. Hai, S. Qian, and Y. Wu The synthesis of pennogenin 3-O-β-D-glucopyranosyl-(1→3)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside J. Asian Nat. Prod. Res. 14 4 2012 314 321
13. S. Ng, M.R. Jafari, W.L. Matochko, and R. Derda Quantitative synthesis of genetically encoded glycopeptide libraries displayed on M13 phage ACS Chem. Biol. 7 9 2012 1482 1487
14. Y. Yang, J. Zhang, Y. Liu, Q. Tang, Z. Zhao, and W. Xia Structural elucidation of a 3-O-methyl-D-galactose-containing neutral polysaccharide from the fruiting bodies of phellinus igniarius Carbohydr. Res. 342 8 2007 1063 1070
15. K. Arumugam, B. Varghese, J.N. Brantley, S.S.M. Konda, V.M. Lynch, and C.W. Bielawski 1,6-Enyne cyclizations catalyzed by N-heterocyclic carbene supported gold complexes: deconvoluting sterics and electronics Eur. J. Org. Chem. 2014 3 2014 493 497
16. C.-C. Zou, S.-J. Hou, Y. Shi, P.-S. Lei, and X.-T. Liang The synthesis of gracillin and dioscin: two typical representatives of spirostanol glycosides Carbohydr. Res. 338 8 2003 721 727
17. F.-Y. Zhou, J. She, and Y.-G. Wang Synthesis of a benzyl-protected analog of arenarioside, a trisaccharide phenylpropanoid glycoside Carbohydr. Res. 341 15 2006 2469 2477