1412427-05-4

Basic information

• Product Name: 2,6-DiaMinopurine -9-beta-D-(2',3',5'-tri-O-benzoyl-2'-C-Methyl) riboside
• Synonyms: 2,6-DiaMinopurine -9-beta-D-(2',3',5'-tri-O-benzoyl-2'-C-Methyl) riboside;2-Amino-2'-C-methyladenosine 2',3',5'-tribenzoate
• CAS NO: 1412427-05-4
• Molecular Formula: C32H28N6O7
• Molecular Weight: 608.61
• Mol File: 1412427-05-4.mol

Chemical Properties

• CAS DataBase Reference: 2,6-DiaMinopurine -9-beta-D-(2',3',5'-tri-O-benzoyl-2'-C-Methyl) riboside(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-DiaMinopurine -9-beta-D-(2',3',5'-tri-O-benzoyl-2'-C-Methyl) riboside(1412427-05-4)
• EPA Substance Registry System: 2,6-DiaMinopurine -9-beta-D-(2',3',5'-tri-O-benzoyl-2'-C-Methyl) riboside(1412427-05-4)

Safety Data

• Hazardous Substances Data: 1412427-05-4(Hazardous Substances Data)

Usage

Molecular Structure

Complex and specific, derived from 2,6-Diaminopurine

Purine Analog

Derived from 2,6-Diaminopurine

Riboside Group

Added to the molecule

Substitutions

Specific benzoyl and methyl substitutions

Biological Activity

Potentially potent due to unique structure

Pharmaceutical Research

Used for potential antiviral and antitumor properties

Medicinal Chemistry

Potential applications in drug development

Therapeutic Potential

Further research needed for full exploration

Upstream product

• 1904-98-9 2,6-diaminopurine 

Downstream Products

• 640725-73-1 (2R,3R,4R,5R)-2-(2,6-diamino-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol 
• 1412427-06-5 (2R,3R,4R,5R)-5-((benzoyloxy)methyl)-2-(2,6-bis(bis(tertbutoxycarbonyl)amino)-9H-purin-9-yl)-3-methyltetrahydrofuran-3,4-diyl dibenzoate 

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.

PURINE MONOPHOSPHATE PRODRUGS FOR TREATMENT OF VIRAL INFECTIONS

The present invention is directed to compounds, compositions and methods for treating or preventing viral infections using nucleoside analog monophosphate prodrugs. More specifically, HCV, Norovirus, Saporovirus, Dengue virus, Chikungunya virus and Yellow fever in human patients or other animal hosts. The compounds are certain 2,6-diamino 2-C-methyl purine nucleoside monophosphate prodrugs and modified prodrug analogs, and pharmaceutically acceptable, salts, prodrugs, and other derivatives thereof. In particular, the compounds show potent antiviral activity against HCV, Norovirus, Saporovirus, Dengue virus, Chikungunya virus and Yellow fever. This invention teaches how to modify the metabolic pathway of 2,6-diamino 2'-C-methyl purine and deliver nucleotide triphosphate(s) to polymerases at heretofore unobtainable therapeutically-relevant concentrations.