Pyrrolidinobenzoic acid inhibitors of influenza virus neuraminidase: The hydrophobic side chain influences type A subtype selectivity

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 14, 2012, Pages 4582-4589

  Li, Yanwu ^a   Silamkoti, Arundutt ^a   Kolavi, Gundurao ^a   Mou, Liyuan ^a   Gulati, Shelly ^b   Air, Gillian M ^b   Brouillette, Wayne J ^a  

^a UNIVERSITY OF ALABAMA AT BIRMINGHAM   (United States)

^b UNIVERSITY OF OKLAHOMA COLLEGE OF MEDICINE   (United States)

Author keywords

Avian influenza; Neuraminidase; Pyrrolidinobenzoic acid

Indexed keywords

4 [2,2 BIS(HYDROXYMETHYL) 5 OXOPYRROLIDIN 1 YL] 3 (2 BUTOXYMETHYL)BENZOIC ACID; 4 [2,2 BIS(HYDROXYMETHYL) 5 OXOPYRROLIDIN 1 YL] 3 (2 ETHYLBUT 1 ENYL)BENZOIC ACID; 4 [2,2 BIS(HYDROXYMETHYL) 5 OXOPYRROLIDIN 1 YL] 3 (2 ETHYLBUTYL)BENZOIC ACID; 4 [2,2 BIS(HYDROXYMETHYL) 5 OXOPYRROLIDIN 1 YL] 3 (2 PROPYLPENTYL)BENZOIC ACID; 4 [2,2 BIS(HYDROXYMETHYL) 5 OXOPYRROLIDIN 1 YL] 3 (3 PENTYLOXY)BENZOIC ACID; 4 [2,2 BIS(HYDROXYMETHYL) 5 OXOPYRROLIDIN 1 YL] 3 (ALKOXYMETHYL)BENZOIC ACID; 4 [2,2 BIS(HYDROXYMETHYL) 5 OXOPYRROLIDIN 1 YL] 3 (HYDROXYMETHYL)BENZOIC ACID; 4 [2,2 BIS(HYDROXYMETHYL) 5 OXOPYRROLIDIN 1 YL] 3 (ISOPROPOXYMETHYL)BENZOIC ACID; 4 [2,2 BIS(HYDROXYMETHYL) 5 OXOPYRROLIDIN 1 YL] 3 (PHENOXYMETHYL)BENZOIC ACID; 4 [2,2 BIS(HYDROXYMETHYL) 5 OXOPYRROLIDIN 1 YL] 3 ISOBUTYLBENZOIC ACID; 5,5 BIS(ETHOXYCARBONYL) 1 (4 METHOXYCARBONYL 2 METHYLPHENYL)PYRROLIDIN 2 ONE; BENZOIC ACID DERIVATIVE; DIETHYL 1 [2 (2 ETHYLBUT 1 ENYL) 4 (METHOXYCARBONYL)PHENYL] 5 OXOPYRROLIDINE 2,2 DICARBOXYLATE; DIETHYL 1 [2 (BROMOMETHYL) 4 (METHOXYCARBONYL)PHENYL] 5 OXOPYRROLIDINE 2,2 DICARBOXYLATE; DIETHYL 1 [4 (METHOXYCARBONYL) 2 (2 METHYLPROP 1 ENYL)PHENYL] 5 OXOPYRROLIDINE 2,2 DICARBOXYLATE; DIETHYL 1 [4 (METHOXYCARBONYL) 2 (2 PROPYLPENT 1 ENYL)PHENYL] 5 OXOPYRROLIDINE 2,2 DICARBOXYLATE; DIETHYL 2 (2 ALKENYL 4 METHOXYCARBONYLPHENYL) 5 OXOPYRROLIDINE 2,2 DICARBOXYLATE; DIETHYL 2 (4 METHOXYCARBONYL 2 METHYLPHENYLAMINO)MALONATE; DIETHYL 2[(3 BROMO PROPIONYL) (4 METHOXYCARBONYL 2 METHYLPHENYL)AMINO]MALONATE; METHYL 3 METHYL 4 NITROBENZOATE; METHYL 4 AMINO 3 (2 ETHYLBUT 1 YNYL)BENZOATE; METHYL 4 AMINO 3 (2 METHYLPROP 1 YNYL)BENZOATE; METHYL 4 AMINO 3 (2 PROPYLPENT 1 YNYL)BENZOATE; METHYL 4 AMINO 3 NITROBENZOATE; PYRROLIDINOBENZOIC ACID DERIVATIVE; SIALIDASE INHIBITOR; UNCLASSIFIED DRUG; VIRUS SIALIDASE;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; CROSS COUPLING REACTION; CRYSTAL STRUCTURE; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; ENZYME INHIBITION; HYDROPHOBICITY; IC 50; INFLUENZA VIRUS; LIPOPHILICITY; MOLECULAR SIZE; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ANTIVIRAL AGENTS; BENZOIC ACID; ENZYME INHIBITORS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; INFLUENZA A VIRUS; INFLUENZA A VIRUS, H1N1 SUBTYPE; INFLUENZA A VIRUS, H3N2 SUBTYPE; NEURAMINIDASE; PYRROLIDINONES; STRUCTURE-ACTIVITY RELATIONSHIP;

AVES; ORTHOMYXOVIRIDAE;

EID: 84863200449     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.05.001     Document Type: Article

References (32)

1. World Health Organization WHO factsheet 211: influenza; 2009 http://www.who.int/mediacentre/factsheets/fs211/en/.
2. R.J. Webby, and R.G. Webster Science 302 2003 1519
3. E.D. Kilbourne Emerg. Infect. Dis. 12 2006 9
4. C. Fraser, C.A. Donnelly, S. Cauchemez, W.P. Hanage, M.D. Van Kerkhove, T.D. Ollingsworth, J. Griffin, R.F. Baggaley, H.E. Jenkins, E.J. Lyons, T. Jombart, W.R. Hinsley, N.C. Grassly, F. Balloux, A.C. Ghani, N.M. Ferguson, A. Rambaut, O.G. Pybus, H. Lopez-Gatell, C.M. Apluche-Aranda, I.B. Chapela, E.P. Zavala, D.M.E. Guevara, F. Checchi, E. Garcia, S. Hugonnet, and C. Roth Science 324 2009 1557
5. K.G. Nicholson Vaccines 8 4 2009 373
6. S. Sambhara, and I. Stephenson Vaccines 8 4 2009 375
7. B. Trollfors Acta Paediatr. 95 7 2006 774
8. F. Carrat, and A. Flahault Vaccine 25 2007 6852
9. P. Palese Nat. Med. 10 2004 S82
10. P.M. Colman R.M. Krug, Influenza Viruses: Influenza Virus Neuraminidase, Enzyme and antigen 1989 Plenum Press New York 175 218
11. G.M. Air, and W.J. Brouillette Influenza virus antiviral targets R. LaFemina, Antiviral Research 2009 ASM Press Washington, DC 187 207
12. M. von Itzstein, W. Wen-Yang, B.K. Gaik, S.P. Michael, C.D. Jeffrey, J. Betty, V.P. Tho, L.S. Mark, F.W. Hume, W.O. Stuart, M.C. Peter, N.V. Joseph, R. Michael, M.W. Jacqueline, C.B. Richard, J.H. Vanessa, M. Janet, J.M. Cameron, and R.P. Charles Nature 363 1993 418 423
13. F.G. Hayden, J.J. Treanor, R.F. Betts, M. Lobo, J.D. Esinhart, and E.K. Hussey J. Am. Med. Assoc. 275 1996 295
14. C.U. Kim, W. Lew, M.A. Williams, H. Liu, L. Zhang, S. Swaminathan, N. Bischofberger, M.S. Chen, D.B. Mendel, C.Y. Tai, W.G. Laver, and R.C. Stevens J. Am. Chem. Soc. 119 1997 681
15. L. Weixing, P.A. Escarpe, E.J. Eisenberg, K.C. Cundy, C. Sweet, K. Jakeman, J. Merson, W. Lew, M. Williams, L. Zhang, C. Kim, N. Bischofberger, M.S. Chen, and D.B. Mendel Antimicrob. Agents Chemother. 42 1998 647
16. Y.S. Babu, P. Chand, S. Bantia, P. Kotian, A. Dehghani, Y. El-Kattan, T. Lin, T.L. Hutchison, A.J. Elliott, C.D. Parker, S.L. Ananth, L.L. Horn, G.W. Laver, and J.A. Montgomery J. Med. Chem. 43 2000 3482
17. G.T. Wang, Y. Chen, S. Wang, R. Gentles, T. Sowin, W. Kati, S. Muchmore, V. Giranda, K. Stewart, H. Sham, D. Kempf, and W.G. Laver J. Med. Chem. 44 2001 1192
18. V. Stoll, K.D. Stewart, C.J. Maring, S. Muchmore, V. Giranda, Y.-G.Y. Gu, G. Wang, Y. Chen, M. Sun, C. Zhao, A.L. Kennedy, D.L. Madigan, Y. Xu, A. Saldivar, W. Kati, G. Laver, T. Sowin, H.L. Sham, J. Greer, and D. Kempf Biochemistry 42 2003 718
19. R.C. Ward Structure 5 1997 1139
20. S. Singh, M.J. Jedrzejas, G.M. Air, M. Luo, G.W. Laver, and W.J. Brouillette J. Med. Chem. 38 1995 3217
21. M.J. Jadrezas, S. Singh, W.J. Brouillette, W.G. Laver, G.M. Air, and M. Luo Biochemistry 34 1995 3144
22. V.R. Atigadda, W.J. Brouillette, F. Duarte, S.M. Ali, Y.S. Babu, S. Bantia, P. Chand, N. Chu, J.A. Montgomery, D.A. Walsh, E.A. Sudbeck, J. Finley, M. Luo, G.M. Air, and G.W. Laver J. Med. Chem. 42 1999 2332
23. W.J. Brouillette, V.R. Atigadda, M. Luo, G.M. Air, S. Babu, and S. Bantia Bioorg. Med. Chem. Lett. 9 1999 1901
24. W.J. Brouillette, S.N. Bajpai, S.M. Ali, S.E. Velu, V.R. Atigadda, B.S. Lommer, J.B. Finley, M. Luo, and G.M. Air Bioorg. Med. Chem. 11 2003 2739
25. P.W. Smith, S.L. Sollis, P.D. Howes, P.C. Cherry, K.N. Cobley, H. Taylor, A.R. Whittington, J. Scicinski, R.C. Bethell, N. Taylor, A.C. Skarzynski, O. Singh, A. Wonacott, J. Varghese, and P. Coleman Bioorg. Med. Chem. Lett. 6 1996 2931
26. S.L. Sollis, P.W. Smith, P.D. Howes, P.C. Cherry, and R.C. Bethell Bioorg. Med. Chem. Lett. 6 1996 1805
27. L. Yang, C.-M. Qi, G.-X. Zhang, and N.-Z. Zou J. Het. Chem. 40 2003 1107
28. S. Bantia, D. Parker, L. Ananth, L. Horn, K. Andries, P. Chand, P. Kotian, A. Dehghani, Y. El-kattan, T. Lin, T. Hutchison, J. Montgomery, D. Kellog, and Y. Babu Antimicrob. Agents Chemother. 45 2001 1162
29. R.J. Russell, L.F. Haire, D.J. Stevens, P.J. Collins, Y.P. Lin, G.M. Blackburn, A.J. Hay, S.J. Gamblin, and J.J. Skehel Nature 443 2006 45
30. P.W. Smith, S.L. Sollis, P.D. Howes, P.C. Cherry, K.N. Cobley, H. Taylor, A.R. Whittington, J. Scicinski, R.C. Bethell, N. Taylor, A.C. Skarzynski, O. Singh, A. Wonacott, J. Varghese, and P. Coleman Bioorg. Med. Chem. Lett. 6 1996 2931
31. S.L. Sollis, P.W. Smith, P.D. Howes, P.C. Cherry, and R.C. Bethell Bioorg. Med. Chem. Lett. 1996 1805 6
32. M. Potier, L. Mameli, M. Belisle, L. Dallaire, and S.B. Melancon Anal. Biochem. 94 1979 287