2009
DOI: 10.1016/j.bmcl.2009.01.035
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Synthesis and evaluation of novel phosphoramidate prodrugs of 2′-methyl cytidine as inhibitors of hepatitis c virus NS5B polymerase

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Cited by 31 publications
(22 citation statements)
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“…used this approach for the synthesis of 2′- C -Me-cytidine aryloxyphosphoramidate prodrugs bearing β-amino alcohols (Scheme 125). 216 2′- C -Me-cytidine was first protected with an isopropylidene group after treatment with 2,2-dimethoxypropane and p -TsOH in acetone in 80% yield. The protected nucleoside was reacted with diphenyl phosphite in pyridine followed by amino alcohol to give 429 in 40% yield over two steps.…”
Section: Nucleoside Monophosphate Prodrugsmentioning
confidence: 99%
“…used this approach for the synthesis of 2′- C -Me-cytidine aryloxyphosphoramidate prodrugs bearing β-amino alcohols (Scheme 125). 216 2′- C -Me-cytidine was first protected with an isopropylidene group after treatment with 2,2-dimethoxypropane and p -TsOH in acetone in 80% yield. The protected nucleoside was reacted with diphenyl phosphite in pyridine followed by amino alcohol to give 429 in 40% yield over two steps.…”
Section: Nucleoside Monophosphate Prodrugsmentioning
confidence: 99%
“…Compound C1 was obtained by derivatization of 2′-methyl cytidine with phosphoramidate pro-drug moiety (Carroll et al, 2009;Donghi et al, 2009). Physico-chemical properties of compound C1 have been calculated using ACD/Labs (ACD/Labs Libraries version 12.01 and LogP Related Properties Algorithm ACD/Labs version B) and are summarized in Figure 2.…”
Section: Methodsmentioning
confidence: 99%
“…Hydrophilic essential cellular nutrients such as nucleosides are efficiently carried across these epithelial Gane et al (2008) barriers by specific transport systems (Majumdar & Mitra, 2006). Derivatization of 2′-methyl cytidine with phosphoramidate pro-drug moiety leading to C1 aimed to increase the liver levels of the nucleoside triphosphate (Carroll et al, 2009;Donghi et al, 2009), and was not completely effective in conferring appropriate permeability properties to the molecule.…”
Section: Introductionmentioning
confidence: 99%
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