Design, synthesis, and structural analysis of influenza neuraminidase inhibitors containing pyrrolidine cores

Journal of Medicinal Chemistry

Volumn 44, Issue 8, 2001, Pages 1192-1201

  Wang, G T ^a   Chen, Y ^a   Wang, S ^a   Gentles, R ^a   Sowin, T ^a   Kati, W ^a   Muchmore, S ^a   Giranda, V ^a   Stewart, K ^a   Sham, H ^a   Kempf, D ^a   Laver, W G ^b  

^a ABBOTT LABORATORIES   (United States)

^b Biology and Environment   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

2 (TRIFLUOROACETAMIDO)METHYL 3 AMINO 1 (N' ETHYL N' ISOPROPYLCARBAMYL)PYRROLIDINE 4 CARBOXYLIC ACID; A 87380; PYRROLIDINE DERIVATIVE; SIALIDASE INHIBITOR; UNCLASSIFIED DRUG; ZANAMIVIR;

ARTICLE; CONFORMATIONAL TRANSITION; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVE SITE; HYDROPHOBICITY; INFLUENZA; X RAY CRYSTALLOGRAPHY;

ANTIVIRAL AGENTS; CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; ENZYME INHIBITORS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NEURAMINIDASE; ORTHOMYXOVIRIDAE; PYRROLIDINES;

EID: 0035848572     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm000468c     Document Type: Article

References (46)

1. Researchers seek new weapon against the flu
2. Serious morbidity and motality associated with influenza epidemics
3. Impact of influenza and respiratory syncytial virus on mortality in England and Wales from January 1975 to December 1990
4. Taking aim at a moving target-inhibitors of influenza virus part 1: Virus adsorption, entry and uncoating
5. Taking aim at a moving target-inhibitors of influenza virus part 2: Viral replication, packaging and release
6. The development of potential anti-influenza drugs
7. Neuraminidase inhibitors as potential anti-influenza drugs
8. The neuraminidase of influenza virus
9. Dihydropyrancarboxamides related to zanamivir: A new series of inhibitors of influenza virus sialidases 1. Discovery, synthesis, biological activity, and structure-activity relationship of 4-guanidino- and 4-amio-4H-pyran-6-carboxamides
10. Dihydropyrancarboxamides related to zanamivir: A new series of inhibitors of influenza virus sialidases 2. Crystallographic and molecular modeling study of complexes of 4-amio-4H-pyran-6-carboxamides and sialidase from influenza virus types A and B
11. Anti-influenza virus activity of the neuraminidase inhibitor 4-guanidino-neu5Ac2en in cell culture and in human respiratory epithelium
12. 4-Guanidino-2,4-dideoxy-2,3-dehydro-N-acetylneuraminic acid is a highly effective inhibitor of both sialidase (neuraminidase) and growth of a wide range of influenza A and B viruese in vitro
13. Inhibition of influenza virus replication in mice by GG167 (4-guanidino-2,4-dideoxy-2,3-dehydro-N-acetylneuraminic acid) is consistent with extracellular activity of viral neuraminidase (sialidase)
14. BCX-1812 (RWJ-270201): Discovery of a novel highly potent, orally active, and selective influenza neuraminidase inhibitor through structure-based drug design
15. Carbocyclic influenza neuraminidase inhibitors possessing a C3-cyclic amine side chain: Synthesis and inhibitory activity
16. Influenza neuraminidase inhibitors possessing a novel hydrophobic interaction in the enzyme active site: Design, synthesis, and structural analysis of carbocyclic sialic acid analogues with potent anti-influenza activity
17. Oral administration of a prodrug of the influenza virus neuraminidase inhibitor GS4071 protects mice and ferrets against influenza infection
18. Identification of GS4104 as an orally bioavailable prodrug of the influenza virus neuraminidase inhibitor GS4071
19. A study of the active site of influenza virus sialidase: An approach to the rational design of novel anti-influenza drugs
20. Molecular modeling studies on ligand binding to sialidase from influenza virus and the mechanism of catalysis
21. Three-dimensional structure of the complex of 4-guanidino-neu5Ac2en and influenza virus neuraminidase
22. Rational design of potent sialidase-based inhibitor of influenza virus replication
23. The structure of Salmonella typhimurium LT2 neuraminidase and its complex with three inhibitors at high resolution
24. Design and synthesis of benzoic acid derivatives as influenza neuraminidase inhibitors using structure-based drug design
25. Synthesis and influenza inhibitory activity of aromatic analogues of sialic acid
26. Structure-based inhibitors of influenza virus sialidase. A benzoic acid lead with novel interaction
27. Synthesis of pyrrole-3-carboxylic acid
28. Neue synthese von β-pyrrolidonen: Darstellung von DL-γ-oxo-prolin, DL-allo-hydroxy-prolin und 4-athoxy-pyrrol-carbonsure-(2)
29. Solid phase synthesis of ureas of secondary amines via carbamyl chloride
30. Solid-phase synthesis of guanidines
31. β-ketoester dianions as regiospecific enolate equivalents for N-substituted pyrrolidin-3-ones
32. Discovery of a novel hydrophobic binding pocket in neuraminidase active site via a combinatorial library of pyrrolidines
33. Progress toward the synthesis of functionalized (±)-(3R,4R,5S)-3,4,5-triamino-cyclohexene-1-carboxylic acid
34. Solid-phase synthesis without repetitive acidolysis
35. Detection of secondary amines on solid phase
36. Enzyme Kinetics
37. Influenza virus neuraminidase with hemaggutinin activity