2001
DOI: 10.1177/095632020101200201
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Furano Pyrimidines as Novel Potent and Selective Anti-VZV Agents

Abstract: Bicyclic furano pyrimidine nucleosides have been found to be highly potent and selective inhibitors of varicella zoster virus (VZV). They are inactive against herpes simplex virus and have been known for several decades as (unwanted) synthetic by-products in the Pd-catalysed coupling of acetylenes to 5-iodo nucleosides. These fluorescent bicyclic nucleosides are now established as a new family of potent antivirals. They are unusual in that they exhibit complete specificity for VZV and require an alkyl (or alky… Show more

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Cited by 35 publications
(48 citation statements)
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“…As noted in all cases with other bicyclic analogues (McGuigan et al, 2001), the present nucleosides displayed no antiviral activity in the thymidine kinase-deficient virus assays (Table 1), which implies an absolute dependence on thymidine kinase-mediated activation for their biological activity. Substrate activity for VZV TK has indeed been demonstrated for several bicyclic nucleoside analogues, including lead compounds 1a and 2e (Sienaert et al, 2002;.…”
Section: Discussionmentioning
confidence: 51%
“…As noted in all cases with other bicyclic analogues (McGuigan et al, 2001), the present nucleosides displayed no antiviral activity in the thymidine kinase-deficient virus assays (Table 1), which implies an absolute dependence on thymidine kinase-mediated activation for their biological activity. Substrate activity for VZV TK has indeed been demonstrated for several bicyclic nucleoside analogues, including lead compounds 1a and 2e (Sienaert et al, 2002;.…”
Section: Discussionmentioning
confidence: 51%
“…The reaction mixture was then heated at 508C for 5 h. The solvent was evaporated, the crude product was dissolved in 200 mL of EtOAc and extracted with 2 Â 100 mL of 10% EDTA solution. The organic layers were combined, dried over MgSO 4 , and evaporated to give 5.05 g of residue. This intermediate trimethylsilyl protected compound was identified using mass spectrometry (Micromass LCT mass spectrometer), ESI+: Theor.…”
Section: Synthesis Of 5-ethynyl-2 0 -Deoxyuridinementioning
confidence: 99%
“…3 Bi-cyclic nucleoside analogs (BCNAs) are novel, lipophilic, potent and selective inhibitors of varicella zoster virus (VZV) with calculated log P (Clog P) values ranging between 0.4 and 4.6. 4 They are synthesized in a two-step reaction. The first step consists of a Sonogashira coupling and usually involves coupling of alkyl-or alkylphenyl acetylenes to the 5-position of the 2 0 -deoxyuridine, under co-catalysis of copper and palladium.…”
Section: Introductionmentioning
confidence: 99%
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“…11,12 Extensive structure--activity relationship (SAR) studies have been carried out with respect to their antiviral activity since their discovery by Mc Guigan et al 11 Of all the BCNAs synthesized and evaluated so far, para-alkylphenyl BCNAs represent the most active series, in particular, the p-pentyl analogue has a potency of about 10 000 times higher than that of the current anti-VZV drug of choice (acyclovir). [13][14][15] Because of their lipophilicity, BCNAs were anticipated to efficiently pass through cellular membranes and biological barriers such as the BBB.…”
Section: Introductionmentioning
confidence: 99%