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Synthesis and biological evaluation of acyclic nucleotide analogues with a furo[2,3-d]pyrimidin-2(3H)-one base
- 1.0345964 - ÚOCHB 2011 RIV CA eng J - Journal Article
Janeba, Zlatko - Holý, Antonín - Pohl, Radek - Snoeck, R. - Andrei, G. - De Clercq, E. - Balzarini, J.
Synthesis and biological evaluation of acyclic nucleotide analogues with a furo[2,3-d]pyrimidin-2(3H)-one base.
Canadian Journal of Chemistry. Roč. 88, č. 7 (2010), s. 628-638. ISSN 0008-4042. E-ISSN 1480-3291
R&D Projects: GA MŠMT 1M0508
Institutional research plan: CEZ:AV0Z40550506
Keywords : acyclic nucleoside phosphonates * Sonogashira reaction * intramolecular cyclization
Subject RIV: CC - Organic Chemistry
Impact factor: 1.374, year: 2010
A novel series of 2-(phosphonomethoxy)ethyl (PME) substituted furo[2,3-d]pyrimidin-2(3H)-ones with potential anti-VZV and/or anti-HCMV activity was synthesized. The target acyclic nucleotide analogues were prepared by Sonogashira coupling of protected 5-iodo-1-[2-(phosphonomethoxy)ethyl]uracil with various 1-alkynes, followed by in situ Cu(I)-promoted intramolecular cyclization and standard removal of the isopropyl ester groups. None of the prepared analogues were active at subtoxic concentrations against VZV thymidine kinase competent (TK+), VZV thymidine kinase deficient (TK–), or HCMV.
Permanent Link: http://hdl.handle.net/11104/0187118
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