Improved synthesis of rupintrivir

Science China Chemistry

Volumn 55, Issue 6, 2012, Pages 1101-1107

  Lin, Daizong ^a   Qian, Wangke ^b   Hilgenfeld, Rolf ^a,c   Jiang, Hualiang ^a   Chen, Kaixian ^a   Liu, Hong ^a  

^a Chinese Academy of Sciences   (China)

^b SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

^c UNIVERSITY OF LÜBECK   (Germany)

Author keywords

AG7088; rupintrivir; synthesis

Indexed keywords

ACID CHLORIDES; ACID DERIVATIVE; AG7088; BUILDING BLOCKES; DIPEPTIDE ISOSTERE; ISOXAZOLES; L-GLUTAMIC ACIDS; L-VALINE; RUPINTRIVIR;

CHLORINE COMPOUNDS; SYNTHESIS (CHEMICAL);

AMINO ACIDS;

EID: 84862552593     PISSN: 16747291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-011-4478-5     Document Type: Conference Paper

References (16)

1. P.C. McMinn 2002 An overview of the evolution of enterovirus 71 and its clinical and public health significance FEMS Microbiol Rev 26 91 107 10.1111/j.1574-6976.2002.tb00601.x 1:CAS:528:DC%2BD38Xjtl2itLw%3D (Pubitemid 34454778)
2. X.N. Zhang Z.G. Song T. Jiang B.S. Shi Y.W. Hu Z.H. Yuan 2010 Rupintrivir is a promising candidate for treating severe cases of Enterovirus-71 infection World J Gastroenterol 16 201 209 10.3748/wjg.v16.i2.201 1:CAS:528: DC%2BC3cXpvVGjsA%3D%3D
3. M.T. Tsai Y.H. Cheng Y.N. Liu N.C. Liao W.W. Lu S.H. Kung 2009 Real-time monitoring of human enterovirus (HEV)-infected cells and anti-HEV 3C protease potency by fluorescence resonance energy transfer Antimicrob Agents Chemother 53 748 755 10.1128/AAC.00841-08 1:CAS:528:DC%2BD1MXhslemsr0%3D
4. H.J. Thibaut P. Leyssen G. Puerstinger A. Muigg J. Neyts A.M. De Palma 2011 Towards the design of combination therapy for the treatment of enterovirus infections Antiviral Res 90 213 217 10.1016/j.antiviral.2011.03.187 1:CAS:528:DC%2BC3MXmvFSktrs%3D
5. H.C. Hung H.C. Wang S.R. Shih I.F. Teng C.P. Tseng J.T. Hsu 2011 Synergistic inhibition of enterovirus 71 replication by interferon and rupintrivir J Infect Dis 203 1784 1790 10.1093/infdis/jir174 1:CAS:528:DC%2BC3MXmvFCht7o%3D
6. K.X. Wu M.M. Ng J.J. Chu 2010 Developments towards antiviral therapies against enterovirus 71 Drug Discov Today 15 1041 1051 10.1016/j.drudis.2010.10. 008 1:CAS:528:DC%2BC3cXhsVOrs7fM
7. pro) structure: Basis for design of anti-SARS drugs Science 300 1763 1767 10.1126/science.1085658 1:CAS:528:DC%2BD3sXksVKisLk%3D (Pubitemid 36712575)
8. E. Jenwitheesuk R. Samudrala 2003 Identifying inhibitors of the SARS coronavirus proteinase Bioorg Med Chem Lett 13 3989 3992 10.1016/j.bmcl.2003.08. 066 1:CAS:528:DC%2BD3sXosVWrsLo%3D (Pubitemid 37338433)
9. H.T. Yang W.Q. Xie X.Y. Xue K.L. Yang J. Ma W.X. Liang Q. Zhao Z. Zhou D.Q. Pei J. Ziebuhr R. Hilgenfeld K.Y. Yuen L. Wong G.X. Gao S.J. Chen Z. Chen D.W. Ma M. Bartlam Z.H. Rao 2005 Design of wide-spectrum inhibitors targeting coronavirus main proteases PLoS Biol 3 e324 10.1371/journal.pbio.0030324 (Pubitemid 41437144)
10. P.S. Dragovich T.J. Prins R. Zhou S.E. Webber J.T. Marakovits S.A. Fuhrman A.K. Patick D.A. Matthews C.A. Lee C.E. Ford B.J. Burke P.A. Rejto T.F. Hendrickson T. Tuntland E.L. Brown J.W. Meador 3rd R.A. Ferre J.E. Harr M.B. Kosa S.T. Worland 1999 Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 4. Incorporation of P1 lactam moieties as L-glutamine replacements J Med Chem 42 1213 1224 10.1021/jm9805384 1:CAS:528:DyaK1MXhvVeisLk%3D (Pubitemid 29181144)
11. P.S. Dragovich T.J. Prins R. Zhou S.A. Fuhrman A.K. Patick D.A. Matthews C.E. Ford J.W. Meador 3rd R.A. Ferre S.T. Worland 1999 Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 3. Structure-activity studies of ketomethylene-containing peptidomimetics J Med Chem 42 1203 1212 10.1021/jm980537b 1:CAS:528: DyaK1MXhvVeisLg%3D (Pubitemid 29181143)
12. Q. Tian N.K. Nayyar S. Babu L. Chen J. Tao S. Lee A. Tibbetts T. Moran J. Liou M. Guo T.P. Kennedy 2001 An efficient synthesis of a key intermediate for the preparation of the rhinovirus protease inhibitor AG7088 via asymmetric dianionic cyanomethylation of N-Boc-l-(+)-glutamic acid dimethyl ester Tetrahedron Lett 42 6807 6809 10.1016/S0040-4039(01)01416-2 1:CAS:528: DC%2BD3MXmslCms7w%3D (Pubitemid 32830891)
13. D.W. Ma W. Xie B. Zou Q. Lei D. Pei 2004 An efficient and tunable route to AG7088, a rhinovirus protease inhibitor Tetrahedron Lett 45 8103 8105 10.1016/j.tetlet.2004.08.179 1:CAS:528:DC%2BD2cXotFGgt74%3D (Pubitemid 39303655)
14. Ma DW, Xie WQ, Zou B. Precursor of key intermediate of AG7088 class compound and its sythetic process. China Patent, 200410017434. 9, 2004-04-02
15. S.S. Chng T.G. Hoang W.W. Lee M.P. Tham H.Y. Ling T.P. Loh 2004 Synthetic studies towards anti-SARS agents: Application of an indium-mediated allylation of α-aminoaldehydes as the key step towards an intermediate Tetrahedron Lett 45 9501 9504 10.1016/j.tetlet.2004.10.146 1:CAS:528:DC%2BD2cXhtVCrur7O (Pubitemid 39574351)
16. J.J. Shie J.M. Fang T.H. Kuo C.J. Kuo P.H. Liang H.J. Huang Y.T. Wu J.T. Jan Y.S. Cheng C.H. Wong 2005 Inhibition of the severe acute respiratory syndrome 3CL protease by peptidomimetic alpha,beta-unsaturated esters Bioorg Med Chem 13 5240 5252 10.1016/j.bmc.2005.05.065 1:CAS:528:DC%2BD2MXmvVKhtb4%3D (Pubitemid 41039985)