113892-17-4

Basic information

• Product Name: cyclic-9-(3-hydroxy-2-phosphonylmethoxypropyl)adenine
• Synonyms: cyclic-9-(3-hydroxy-2-phosphonylmethoxypropyl)adenine
• CAS NO: 113892-17-4
• Molecular Formula: C₉H₁₂N₅O₄P
• Molecular Weight: 285.196441
• Mol File: 113892-17-4.mol

Chemical Properties

• Boiling Point: 606°Cat760mmHg
• Flash Point: 320.3°C
• Appearance: /
• Density: 2.01g/cm³
• Vapor Pressure: 1.55E-15mmHg at 25°C
• Refractive Index: 1.839
• CAS DataBase Reference: cyclic-9-(3-hydroxy-2-phosphonylmethoxypropyl)adenine(CAS DataBase Reference)
• NIST Chemistry Reference: cyclic-9-(3-hydroxy-2-phosphonylmethoxypropyl)adenine(113892-17-4)
• EPA Substance Registry System: cyclic-9-(3-hydroxy-2-phosphonylmethoxypropyl)adenine(113892-17-4)

Safety Data

• Hazardous Substances Data: 113892-17-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H12N5O4P/c10-8-7-9(12-3-11-8)14(4-13-7)1-6-2-18-19(15,16)5-17-6/h3-4,6H,1-2,5H2,(H,15,16)(H2,10,11,12)/t6-/m0/s1

Upstream product

• 1322511-03-4 O-[(5S)-5-[(6-amino-9H-purin-9-yl)methyl]-2-oxido-1,4,2-dioxaphosphinan-2-yl]-N-(2-methylpropyl)-(L)-tyrosinamide trifluoroacetate 
• 631-61-8 ammonium acetate 
• 1345667-16-4 iso-butyl (2S)-2-amino-3-(4-{[(2R,5S)-5-[(6-amino-9H-purin-9-yl)methyl]-2-oxo-1,4,2λ5-dioxaphosphinan-2-yl]oxy}phenyl)-propanoate 
• 1322511-11-4 iso-butyl (2S)-2-amino-3-(4-{[(2S,5S)-5-[(6-amino-9H-purin-9-yl)methyl]-2-oxo-1,4,2λ5-dioxaphosphinan-2-yl]oxy}phenyl)-propanoate 

Relevant articles and documents

Method to improve antiviral activity of nucleotide analogue drugs

An amino acid conjugate of a cyclic or acyclic nucleoside phosphonate is provided. In some cases, the amino acid conjugate is a tyrosine alkyl amide phosphonate ester conjugate of a cyclic or acyclic nucleoside phosphonate, and is useful as an antiviral c

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%).

TYROSINE-BASED PRODRUGS OF ANTIVIRAL AGENTS

A tyrosine-based (phosphonylmethoxyalkyl)purine or -pyrimidine conjugate is provided. In some embodiments, the conjugate includes tyrosine based amino acid or dipeptide moieties of (S)-9-(3-hydroxy-2-phosphonyl-methoxypropyl)adenine or its cytosine analogue. A method of synthesizing such conjugates based on Boc-protected amino acid or dipeptides is also provided. In addition, a method of isomerizing an (S,S)-diastereoisomer to an (S,R)-diastereoisomer of an amino acid-based or dipeptide-based conjugate by a process including transesterification is provided. A method of inhibiting viral infection and a method of treating viral infection based on (phosphonylmethoxyalkyl)purine or -pyrimidine conjugates is also provided.