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Development of novel potent orally bioavailable oseltamivir derivatives active against resistant influenza A.

Abstract：

:With the emergence of oseltamivir-resistant influenza viruses and in view of a highly pathogenic flu pandemic, it is important to develop new anti-influenza agents. Here, the development of neuraminidase (NA) inhibitors that were designed to overcome resistance mechanisms along with unfavorable pharmacokinetic (PK) properties is described. Several 5-guanidino- and 5-amidino-based oseltamivir derivatives were synthesized and profiled for their anti-influenza activity and in vitro and in vivo PK properties. Amidine 6 and guanidine 7 were comparably effective against a panel of different A/H1N1 and A/H3N2 strains and also inhibited mutant A/H1N1 neuraminidase. Among different prodrug strategies pursued, a simple amidoxime ethyl ester (9) exhibited a superior PK profile with an oral bioavailability of 31% (rats), which is comparable to oseltamivir (36%). Thus, bioisosteric replacement of the 5-guanidine with an acetamidine-in the form of its N-hydroxy prodrug-successfully tackled the two key limitations of currently used NA inhibitors, as exemplified with oseltamivir.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Schade D,Kotthaus J,Riebling L,Kotthaus J,Müller-Fielitz H,Raasch W,Koch O,Seidel N,Schmidtke M,Clement B

doi

10.1021/jm401492x

subject

Has Abstract

pub_date

2014-02-13 00:00:00

pages

759-69

issue

3

eissn

0022-2623

issn

1520-4804

journal_volume

57

pub_type

杂志文章

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