142341-24-0

Basic information

• Product Name: diphenyl {[2-(6-amino-9H-purin-9-yl)ethoxy]methyl}phosphonate
• Synonyms: Phosphonic acid, ((2-(6-amino-9H-purin-9-yl)ethoxy)methyl)-, diphenyl ester; Phosphonic acid, [[2-(6-amino-9H-purin-9-yl)ethoxy]methyl]-, diphenyl ester
• CAS NO: 142341-24-0
• Molecular Formula: C₂₀H₂₀N₅O₄P
• Molecular Weight: 425.3777
• Mol File: 142341-24-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 635.4°C at 760 mmHg
• Flash Point: 338.1°C
• Density: 1.42g/cm³
• Vapor Pressure: 4.79E-16mmHg at 25°C
• Refractive Index: 1.667
• CAS DataBase Reference: diphenyl {[2-(6-amino-9H-purin-9-yl)ethoxy]methyl}phosphonate(CAS DataBase Reference)
• NIST Chemistry Reference: diphenyl {[2-(6-amino-9H-purin-9-yl)ethoxy]methyl}phosphonate(142341-24-0)
• EPA Substance Registry System: diphenyl {[2-(6-amino-9H-purin-9-yl)ethoxy]methyl}phosphonate(142341-24-0)

Safety Data

• Hazardous Substances Data: 142341-24-0(Hazardous Substances Data)

Upstream product

• 142341-38-6 C₈H₁₀Cl₂N₅O₂P 
• 108-95-2 phenol 
• 106941-25-7 Adefovir 

Downstream Products

• 158421-65-9 2,2-Dimethyl-propionic acid [2-(6-amino-purin-9-yl)-ethoxymethyl]-benzyloxy-phosphinoyloxymethyl ester 
• 142341-05-7 9-<2-(phosphonomethoxy)ethyl>adenine, mono(pivaloyloxy)methyl ester 

Relevant articles and documents

PHOSPHORIC ACID/PHOSPHONIC ACID DERIVATIVES AND MEDICINAL USES THEREOF

The present invention relates to phosphoric acid/phosphonic acid derivatives shown by formula (I), wherein, R1 or R2 represents the following structures: (Q1), or (Q2), or (Q3). Q1 represents ester derivatives of L-amino acid, wherein R3 is alkyl with 1-6 carbon atoms or cycloalkyl, R4 is H or alkyl with 1-6 carbon atoms; Q2 represents hydroxyl substituted benzodioxane derivatives; Q3 represents hydroxyl substituted benzodioxolane derivatives; R1 or R2 is the same or different, but at least one of them is Q2 or Q3; D represents residues of pharmacologically active molecules containing a phosphate/phosphonate group, i.e. formula (II) represents pharmacologically active molecules containing a phosphate/phosphonate group; and when R1 and R2 are different, the configuration of the P atom connected to R1 and R2 is of R or S type.

Synthesis, Oral Bioavailability Determination, and in Vitro Evaluation of Prodrugs of the Antiviral Agent 9-adenine (PMEA)

A series of phosphonate prodrugs were evaluated in an attempt to increase the oral bioavailability of the anti-HIV agent 9-adenine (PMEA; 1).The majority of the bis(alkyl ester) and bis(alkyl amide) prodrugs were prepared by alcohol or amine displacement of dichlorophosphonate 2.Basic hydrolysis of the bis(esters) or bis(amides) provides the corresponding monoesters or momoamides.Synthesis of bis phosphonates 10a-c was accomplished by alkylation of PMEA with the appropriate chloromethyl ether in the presence of N,N'-dicyclohexylmorpholinecarboxamidine.The systemic levels of PMEA following oral administration of a PMEA prodrug to rats were determined by measuring the concentration of PMEA in the urine for 48 h after administration of the prodrug.The oral bioavailability of PMEA employing this method was determined to be 7.8percent.Oral dosing with bis(alkyl) phosphonates 3a,b resulted in apparent absorption of the prodrugs (equal or >40percent), although neither of the esters were completely cleaved to liberate the parent phosphonate PMEA.The mono(alkyl esters) 7a-e and 8a,b exhibited poor oral bioavailability (equal or phosphonates 10a-c demonstrated significantly improved oral bioavailabilities of 17.6percent, 14.6percent, and 15.4percent, respectively.When evaluated in vitro against HSV-2, (acyloxy)alkyl phosphonates 10a-c were greater than 200-fold more active than PMEA.