1412427-12-3

Basic information

• Product Name: ethyl 3-(2-(((((2R,3S,4R,5R)-5-(2,6-diamino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(2-(3-ethoxy-3-oxopropyl)phenoxy)phosphoryl)oxy)phenyl)propanoate
• Synonyms: ethyl 3-(2-(((((2R,3S,4R,5R)-5-(2,6-diamino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(2-(3-ethoxy-3-oxopropyl)phenoxy)phosphoryl)oxy)phenyl)propanoate
• CAS NO: 1412427-12-3
• Molecular Weight: 1129.17
• Mol File: 1412427-12-3.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: ethyl 3-(2-(((((2R,3S,4R,5R)-5-(2,6-diamino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(2-(3-ethoxy-3-oxopropyl)phenoxy)phosphoryl)oxy)phenyl)propanoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 3-(2-(((((2R,3S,4R,5R)-5-(2,6-diamino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(2-(3-ethoxy-3-oxopropyl)phenoxy)phosphoryl)oxy)phenyl)propanoate(1412427-12-3)
• EPA Substance Registry System: ethyl 3-(2-(((((2R,3S,4R,5R)-5-(2,6-diamino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(2-(3-ethoxy-3-oxopropyl)phenoxy)phosphoryl)oxy)phenyl)propanoate(1412427-12-3)

Safety Data

• Hazardous Substances Data: 1412427-12-3(Hazardous Substances Data)

Upstream product

• 20921-04-4 ethyl 3-(2-hydroxyphenyl)propanoate 
• 119-84-6 C₆H₄(CH₂CH₂C(O)O) 
• 1412427-11-2 diethyl 3,3′-(((chlorophosphoryl)bis(oxy))bis(2,1-phenylene))dipropanoate 
• 1412427-07-6 di-tert-butyl (9-((2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)-9H-purine-2,6-diyl)bis-(tert-butoxycarbonylcarbamate) 

Downstream Products

• 1412427-13-4 ethyl 3-(2-(((((2R, 3R,4R,5R)-5-(2,6-diamino-9H-purin-9-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy) (2-(3-ethoxy-3-oxopropyl)phenoxy)phosphoryl)oxy)phenyl)propanoate 

Relevant articles and documents

β-D-2′-C-methyl-2,6-diaminopurine ribonucleoside phosphoramidates are potent and selective inhibitors of hepatitis C virus (HCV) and are bioconverted intracellularly to bioactive 2,6-diaminopurine and guanosine 5′-triphosphate forms

The conversion of selected β-d-2,6-diaminopurine nucleosides (DAPNs) to their phosphoramidate prodrug (PD) substantially blocks the conversion to the G-analog allowing for the generation of two bioactive nucleoside triphosphates (NTPs) in human hepatocytes. A variety of 2′-C-methyl DAPN-PDs were prepared and evaluated for inhibition of HCV viral replication in Huh-7 cells, cytotoxicity in various cell lines, and cellular pharmacology in both Huh-7 and primary human liver cells. The DAPN-PDs were pan-genotypic, effective against various HCV resistant mutants, and resistant variants could not be selected. 2′-C-Me-DAPN-TP and 2′-C-Me-GTP were chain terminators for genotype 1b HCV-pol, and single nucleotide incorporation assays revealed that 2′-C-Me-DAPN-TP was incorporated opposite U. No cytotoxicity was observed with our DAPN-PD when tested up to 50 μM. A novel, DAPN-PD, 15c, has been selected for further evaluation because of its good virologic and toxicologic profile and its ability to deliver two active metabolites, potentially simplifying HCV treatment.