1322510-40-6

Basic information

• Product Name: isopropyl O-[(5S)-5-[(4-amino-2-oxopyrimidin-1(2H)-yl)methyl]-2-oxido-1,4,2-dioxaphosphinan-2-yl]-N-(tert-butoxycarbonyl)-(L)-tyrosinate
• Synonyms: isopropyl O-[(5S)-5-[(4-amino-2-oxopyrimidin-1(2H)-yl)methyl]-2-oxido-1,4,2-dioxaphosphinan-2-yl]-N-(tert-butoxycarbonyl)-(L)-tyrosinate
• CAS NO: 1322510-40-6
• Molecular Weight: 566.548
• Mol File: 1322510-40-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: isopropyl O-[(5S)-5-[(4-amino-2-oxopyrimidin-1(2H)-yl)methyl]-2-oxido-1,4,2-dioxaphosphinan-2-yl]-N-(tert-butoxycarbonyl)-(L)-tyrosinate(CAS DataBase Reference)
• NIST Chemistry Reference: isopropyl O-[(5S)-5-[(4-amino-2-oxopyrimidin-1(2H)-yl)methyl]-2-oxido-1,4,2-dioxaphosphinan-2-yl]-N-(tert-butoxycarbonyl)-(L)-tyrosinate(1322510-40-6)
• EPA Substance Registry System: isopropyl O-[(5S)-5-[(4-amino-2-oxopyrimidin-1(2H)-yl)methyl]-2-oxido-1,4,2-dioxaphosphinan-2-yl]-N-(tert-butoxycarbonyl)-(L)-tyrosinate(1322510-40-6)

Safety Data

• Hazardous Substances Data: 1322510-40-6(Hazardous Substances Data)

Upstream product

• 126530-25-4 isopropyl N-(tert-butoxycarbonyl)-(L)-tyrosinate 
• 113852-37-2 cidofovir 
• 60-18-4 L-tyrosine 
• 1322510-76-8 isopropyl O-[(5S)-5-[(4-amino-2-oxopyrimidin-1(2H)-yl)methyl]-2-oxido-1,4,2-dioxaphosphinan-2-yl]-N-(tert-butoxycarbonyl)-(L)-tyrosinate 

Relevant articles and documents

Tyrosine-based 1-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]cytosine and -adenine ((S)-HPMPC and (S)-HPMPA) prodrugs: Synthesis, stability, antiviral activity, and in vivo transport studies

Eight novel single amino acid (6-11) and dipeptide (12, 13) tyrosine P-O esters of cyclic cidofovir ((S)-cHPMPC, 4) and its cyclic adenine analogue ((S)-cHPMPA, 3) were synthesized and evaluated as prodrugs. In vitro IC 50 values for the prodrugs (50 0.3-35 μM); there was no cytoxicity with KB or HFF cells at ≤100 μM. The prodrugs exhibited a wide range of half-lives in rat intestinal homogenate at pH 6.5 (30-1732 min) with differences of 3-10× between phostonate diastereomers. The tyrosine alkylamide derivatives of 3 and 4 were the most stable. (l)-Tyr-NH-i-Bu cHPMPA (11) was converted in rat or mouse plasma solely to two active metabolites and had significantly enhanced oral bioavailability vs parent drug 1 in a mouse model (39% vs 5%).