138247-60-6

Basic information

• Product Name: ({[(2R)-1-(2-amino-6-oxo-3,6-dihydro-9H-purin-9-yl)propan-2-yl]oxy}methyl)phosphonic acid
• Synonyms: ({[(2R)-1-(2-amino-6-hydroxy-9H-purin-9-yl)propan-2-yl]oxy}methyl)phosphonic acid; Phosphonic acid, (((1R)-2-(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)-1-methylethoxy)methyl)-; Phosphonic acid, [[(1R)-2-(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)-1-methylethoxy]methyl]-; phosphonic acid, [[(1R)-2-(2-amino-6-hydroxy-9H-purin-9-yl)-1-methylethoxy]methyl]-
• CAS NO: 138247-60-6
• Molecular Formula: C₉H₁₄N₅O₅P
• Molecular Weight: 303.2117
• Mol File: 138247-60-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 702°C at 760 mmHg
• Flash Point: 378.3°C
• Density: 1.92g/cm³
• Vapor Pressure: 1.1E-20mmHg at 25°C
• Refractive Index: 1.769
• CAS DataBase Reference: ({[(2R)-1-(2-amino-6-oxo-3,6-dihydro-9H-purin-9-yl)propan-2-yl]oxy}methyl)phosphonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: ({[(2R)-1-(2-amino-6-oxo-3,6-dihydro-9H-purin-9-yl)propan-2-yl]oxy}methyl)phosphonic acid(138247-60-6)
• EPA Substance Registry System: ({[(2R)-1-(2-amino-6-oxo-3,6-dihydro-9H-purin-9-yl)propan-2-yl]oxy}methyl)phosphonic acid(138247-60-6)

Safety Data

• Hazardous Substances Data: 138247-60-6(Hazardous Substances Data)

Upstream product

• 1443683-73-5 C₁₃H₂₁ClN₅O₄P 
• 352211-52-0 C₈H₁₀ClN₅O 
• 10310-21-1 2-Amino-6-chloropurin 
• 160616-37-5 (R)-9-(2-hydroxypropyl)guanine 
• 138271-96-2 (S)-2-amino-6-chloro-9-<2-<(diisopropylphosphono)methoxy>propyl>purine 
• 170169-11-6 [(R)-2-(2-Amino-6-oxo-1,6-dihydro-purin-9-yl)-1-methyl-ethoxymethyl]-phosphonic acid diisopropyl ester 
• 170169-11-6 bis(2-propyl) (R)-9-(2-phosphonomethoxypropyl)guanine 
• 160616-48-8 [(R)-2-(2-Benzoylamino-6-oxo-1,6-dihydro-purin-9-yl)-1-methyl-ethoxymethyl]-phosphonic acid diisopropyl ester 
• 160616-45-5 (R)-9-(2-hydroxypropyl)-N²-benzoylguanine 
• 160616-38-6 (R)-9-<2-(2-tetrahydropyranyloxy)propyl>2-amino-6-chloropurine 

Relevant articles and documents

Inhibition of human purine nucleoside phosphorylase by tenofovir phosphate congeners

The structure-activity study on the phosphates of phosphonomethoxypropyl derivatives of purine bases interacting with human purine nucleoside phosphorylase has shown that the most efficient inhibitors of the enzyme are (R)- and (S)-PMPGp with Ki ~ 1.9 × 10-8 and/or 2.2 × 10-8 mol/l. The kinetic experiments have proven, with the exception of both enantiomers of PMP-8-BrDAPp, strictly competitive character of inhibition for all ANP monophosphates tested. Bromine derivatives exhibited uncompetitive and mixed type of inhibition as well. These results were confirmed by docking studies. The substitution of purine moiety with the bromine at the position 8 lead to an allosteric binding of these compounds toward the enzyme.

SYNTHESIS OF ENANTIOMERIC N-(2-PHOSPHONOMETHOXYPROPYL) DERIVATIVES OF PURINE AND PYRIMIDINE BASES. I. THE STEPWISE APPROACH

The (R)- and (S)-N-(2-phosphonomethoxypropyl) derivatives of purine and pyrimidine bases (PMP derivatives) exhibit very high activity against retroviruses.This paper describes the synthesis of enantiomeric 9-(2-phosphonomethoxypropyl)adenines (I and XXVII), 9-(2-phosphonomethoxypropyl)-2,6-diaminopurines (II and XXXI), 9-(2-phosphonomethoxypropyl)guanines (III and XXIX) and 1-(R)-(2-phosphonomethoxypropyl)cytosine (XIX) by alkylation of N-protected N-(2-hydroxypropyl) derivatives of the corresponding bases with bis(2-propyl) p-toluenesulfonyloxymethylphosphonate (X), followed by stepwise N- and O-deprotection of the intermediates.The key intermediates, N-(2-hydropxypropyl) derivatives IX and XXV, were obtained by alkylation of the appropriate heterocyclic base with (R)- or (S)-2-(2-tetrahydropyranyloxy)propyl p-toluenesulfonate (VII or XXIII) ans acid hydrolysis of the resulting N- derivatives VIII and XXII.The chiral synthons were prepared by tosylation of (R)- or (S)-2-(2-tetrahydropyranyloxy)propanol (VI or XXI) available by reduction of enantiomeric alkyl 2-O-tetrahydropyranyllactates V and XXI with sodium bis(2-methoxyethyoxy)aluminum hydride.This approach was used for the synthsis of cytosine, adenine and 2,6-diaminopurine derivatives, while compounds derived from guanine were prepared by hydrolysis of 2-amino-6-chloropurine intermediates.Cytosine derivative IXe was also synthesized by alkylation of 4-methoxy-2-pyrimidone followed by ammonolysis of the intermediate IXf.

Synthesis and antiviral activity of methyl derivatives of 9-[2- (phosphonomethoxy)ethyl]guanine

A number of methyl derivatives of 9-[2-(phosphonomethoxy)ethyl]guanine (PMEG, 1) have been synthesized and tested in vitro for anti-herpes and anti- human immunodeficiency virus (HIV) activity. Among these analogues, (R)-2'- methyl-PMEG [(R)-3] and 2',2'-