190141-28-7Relevant articles and documents
Chemical and enzymatic stability of amino acid derived phosphoramidates of antiviral nucleoside 5′-monophosphates bearing a biodegradable protecting group
Leisvuori, Anna,Aiba, Yuichiro,Loennberg, Tuomas,Poijaervi-Virta, Paeivi,Blatt, Laurence,Beigelman, Leo,Loennberg, Harri
, p. 2131 - 2141 (2010)
Ribavirin and 2′-O-methylcytidine 5′-phosphoramidates derived from l-alanine methyl ester bearing either an O-phenyl or a biodegradable O-[3-(acetyloxy)-2,2-bis(ethoxycarbonyl)propyl] or O-[3-(acetyloxymethoxy)-2,2- bis(ethoxycarbonyl)propyl] protecting group were prepared. The kinetics of the deprotection of these pro-drugs by porcine liver esterase and by a whole cell extract of human prostate carcinoma was studied by HPLC-ESI-MS/MS. The 3-(acetyloxymethoxy)-2,2-bis(ethoxycarbonyl)propyl and 3-(acetyloxy)-2,2- bis(ethoxycarbonyl)propyl groups were readily removed releasing the l-alanine methyl ester phosphoramidate nucleotide, the deprotection of the 3-(acetyloxymethoxy) derivative being approximately 20 times faster. The chemical stability of the 2′-O-methylcytidine pro-drugs was additionally determined over a pH range from 7.5 to 10.
PROTECTED NUCLEOTIDE ANALOGS
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Page/Page column 34-35, (2009/07/18)
Disclosed herein are nucleotide analogs with one or more protecting groups, methods of synthesizing nucleotide analogs with one or more protecting groups and methods of treating diseases and/or conditions such as viral infections, cancer, and/or parasitic