Synthesis and influenza virus sialidase inhibitory activity of analogues of 4-Guanidino-Neu5Ac2en (Zanamivir) modified in the glycerol side-chain

Authors
Andrews, DM Cherry, PC Humber, DC Jones, PS Keeling, SP Martin, PF Shaw, CD Swanson, S
Citation
Dm. Andrews et al., Synthesis and influenza virus sialidase inhibitory activity of analogues of 4-Guanidino-Neu5Ac2en (Zanamivir) modified in the glycerol side-chain, EUR J MED C, 34(7-8), 1999, pp. 563-574
Citations number
22
Categorie Soggetti
Chemistry & Analysis
Journal title
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
ISSN journal
02235234 → ACNP
Volume
34
Issue
7-8
Year of publication
1999
Pages
563 - 574
Database
ISI
SICI code
0223-5234(199907/08)34:7-8<563:SAIVSI>2.0.ZU;2-K
Abstract
Analogues of 4-Guanidino-Neu5Ac2en (Zanamivir) have been prepared containin g carbamate substituents at the 7-hydroxy position. (4S,SR,6R)-5-Acetylamin o-6-{1R-[(6-aminohexyl)carbamoyloxyl-2R,3-dihydroxypropyl}-4-guanidino-5,6- dihydro-4H-pyran-2-carboxylic acid and (4S,SR,6R)-5-Acetylamino-6-{1R-Chept ylcarbamoyloxyl-2R,3-dihydroxypropyl}-4-guanidino-5,6-dihydro4H-pyran-2-car boxylic acid were the two analogues possessing activity comparable to Zanam ivir, showing potent inhibition of influenza virus sialidases and good anti viral activity in vitro. (C) 1999 Editions scientifiques ct medicales Elsev ier SAS.