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Design and synthesis of novel non-nucleoside anti-HCMV agents [Abstract]

Adak, Rina, McGuigan, Christopher, Snoeck, R., Andrei, G., Balzarini, J., Gorovits, E., Chang, C., Ames, B., Liu, Y. and Vernachio, J. 2008. Design and synthesis of novel non-nucleoside anti-HCMV agents [Abstract]. Antiviral Research 78 (2) , A52. 10.1016/j.antiviral.2008.01.107

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Abstract

Bicyclic furanopyrimidines are potent and selective inhibitors of Varicella Zoster Virus (VZV) (McGuigan et al., 1999). SAR studies have shown 2′,3′-dideoxynucleoside derivatives to be poorly VZV-active but exhibit activity against human cytomegalovirus (HCMV) (McGuigan et al., 2004). Phosphorylation was shown not to be a requisite for activity presenting the possibility to introduce non-sugar moieties. Many long chain N- and O-alkylated derivatives have been presented, some showing comparable activity to ganciclovir (GCV) supporting a non-nucleoside meachanism of action (Kelleher et al., 2005 and Adak et al., 2007). The target structures were prepared by the Pd-catalysed coupling of various alkynes with 5-iodouracil (Scheme 1), to give intermediate 5-alkynyl nucleosides which were subsequently cyclised in the presence of CuI to give the bicyclic systems. The corresponding bases were then reacted with a selection of alkylating agents to form N- and O-alkylated products. The synthesis, biological evaluation and cytotoxicity of novel long chain N- and O-alkylated derivatives will be presented.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Pharmacy
Systems Immunity Research Institute (SIURI)
Additional Information: Poster Session II: Herpesviruses, Topical Microbicides, Poxviruses, Other Antiviral Agents, Medicinal. Abstract no. 93
Publisher: Elsevier
ISSN: 0166-3542
Last Modified: 18 Oct 2017 13:04
URI: http://orca-mwe.cf.ac.uk/id/eprint/6402

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