Synthesis and anti-influenza virus activity of 7-O-alkylated derivatives related to zanamivir

…, S Yoshida, M Arai, S Kaneko, M Yamashita

Index: Honda, Takeshi; Masuda, Takeshi; Yoshida, Shuku; Arai, Masami; Kaneko, Satoru; Yamashita, Makoto Bioorganic and Medicinal Chemistry Letters, 2002 , vol. 12, # 15 p. 1925 - 1928

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Citation Number: 74

Abstract

A series of 7-alkyl ether derivatives related to zanamivir were synthesized using direct alkylation of the C-7 alcohol of sialic acid. Alkyl ether moiety of less than 12 carbons in length showed low nanomolar inhibitory activity against influenza A virus sialidase. Furthermore, their moiety improved influenza A virus plaque reduction activity compared to zanamivir. However, removal of the 8, 9-diol of the 7-O-alkyl derivatives resulted in loss of ...