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Derivatives of imidazotriazine and pyrrolotriazine C-nucleosides as potential new anti-HCV agents. 2014
Alistair G Draffan, and
Barbara Frey, and
Benjamin H Fraser, and
Brett Pool, and
Carlie Gannon, and
Edward M Tyndall, and
Julia Cianci, and
Michael Harding, and
Michael Lilly, and
Richard Hufton, and
Rosliana Halim, and
Saba Jahangiri, and
Silas Bond, and
Tyrone P Jeynes, and
Van T T Nguyen, and
Veronika Wirth, and
Angela Luttick, and
Danielle Tilmanis, and
Melinda Pryor, and
Kate Porter, and
Craig J Morton, and
Bo Lin, and
Jianmin Duan, and
Richard C Bethell, and
George Kukolj, and
Bruno Simoneau, and
Simon P Tucker
Biota Scientific Management Pty. Ltd, 10/585 Blackburn Road, Notting Hill, Victoria 3168, Australia.
Previous investigations identified 2'-C-Me-branched ribo-C-nucleoside adenosine analogues, 1, which contains a pyrrolo[2,1-f][1,2,4]triazin-4-amine heterocyclic base, and 2, which contains an imidazo[2,1-f][1,2,4]triazin-4-amine heterocyclic base as two compounds with promising anti-HCV in vitro activity. This Letter describes the synthesis and evaluation of a series of novel analogues of these compounds substituted at the 2-, 7-, and 8-positions of the heterocyclic bases. A number of active new HCV inhibitors were identified but most compounds also demonstrated unacceptable cytotoxicity. However, the 7-fluoro analogue of 1 displayed good potency with a promising cytotherapeutic margin.
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