640725-74-2

Usage

Structure

Consists of a purine base with a ribose sugar attached.

Functional Groups

Amino group (-NH?) at position 2 of the purine ring.
Chlorine atom (Cl) at position 6 of the purine ring.
Methyl group (-CH?) attached to the ribose sugar at position 2.

Nucleoside Analog

Acts as a nucleoside analog.

Antiviral Activity

Exhibits antiviral activity against various types of viruses.

Mechanism of Action

Disrupts viral replication process by being incorporated into viral RNA or DNA during replication.

Potential Therapeutic Use

Can be used in the treatment of viral infections.

Structural Similarity

Similar to natural nucleosides, facilitating its incorporation into viral nucleic acids.

Specific Functionality

The chlorine atom and methyl group contribute to its antiviral activity and specificity against certain viruses.

Research Implications

Holds promise for the development of new antiviral therapies.

Upstream product

• 641571-44-0 (2R,3R,4R,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-5-(benzoyloxymethyl)-3-methyltetrahydrofuran-3,4-diyl dibenzoate 
• 10310-21-1 2-Amino-6-chloropurin 

Downstream Products

• 1412427-32-7 isopropyl 3-(2-(((((2 R,3R,4R,5R)-5-(2-amino-6-chloro-9H-purin-9-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(((S)-1-isopropoxy-1-oxopropan-2-yl)amino)phosphoryl)oxy)phenyl)propanoate 
• 1336975-57-5 2-(2-amino-6-dimethylamino-9H-purin-9-yl)-5-hydroxymethyl-3-methyltetrahydrofuran-3,4-diol 
• 1412427-38-3 isopropyl 3-(2-(((((3aR,4R,6R,6aR)-6-(2,6-diamino-9H-purin-9-yI)-6a-methyl-2-oxotetrahydrofuro[3,4-d][1,3]dioxoI-4-yI)methoxy)(((S)-1-isopropoxy-1-oxopropan-2-yI)amino)phosphoryl)oxy)phenyl)propanoate 
• 1412427-39-4 isopropyl 3-(2-(((((3aR,4R,6R,6aR)-6-(2,6-diamino-9H-purin-9-yI)-6a-methyl-2-oxotetrahydrofuro[3,4-d][1,3]dioxoI-4-yI)methoxy)(((S)-1-isopropoxy-1-oxopropan-2-yI)amino)phosphoryl)oxy)phenyl)propanoate 
• 1412427-37-2 isopropyl 3-(2-(((((3aR,4R,6R,6aR)-6-(2-amino-6-chIoro-9H-purin-9-yI)-6a-methyl-2-oxotetrahydrofuro[3,4-d][1,3]dioxoI-4-yI)methoxy)(((S)-1-isopropoxy-1-oxopropan-2-yI)amino)phosphoryl)oxy)phenyl)propanoate 
• 1412427-34-9 isopropyl 3-(2-(((R)-(((2R,3R,4R,5R)-5-(2,6-diamino-9H-purin-9-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(((S)-1-isopropoxy-1-oxopropan-2-yl)amino)phosphoryl)oxy)phenyl)propanoate 
• 1412427-33-8 isopropyl 3-(2-(((S)-(((2R,3R,4R,5R)-5-(2,6-diamino-9H-purin-9-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)-(((S)-1-isopropoxy-1-oxopropan-2-yl)amino)phosphoryl)oxy)-phenyl)propanoate 
• 1422526-26-8 C₂₉H₄₀N₉O₁₀P 
• 1365634-73-6 1-(2-amino-6-chloropurin-9-yl)-2-C-methyl-β-D-ribofuranose 5'-(O-phenyl-N-(S)-1-(isopropoxycarbonyl)ethyl)thiophosphoramidate 
• 374750-30-8 2'-C-methylguanosine 
• 640725-73-1 (2R,3R,4R,5R)-2-(2,6-diamino-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol 

Relevant academic research and scientific papers

Intracellular metabolism and potential cardiotoxicity of a β-D-2’-C-methyl-2,6-diaminopurine ribonucleoside phosphoramidate that inhibits hepatitis C virus replication

β-D-2’-C-Methyl-2,6-diaminopurine ribonucleoside (2’-C-Me-DAPN) phosphoramidate prodrug (DAPN-PD) is a selective hepatitis C virus inhibitor that is metabolized intracellularly into two active metabolites: 2’-C-Methyl-DAPN triphosphate (2’-C-Me-DAPN-TP) a

2'-SUBSTITUTED-N6-SUBSTITUTED PURINE NUCLEOTIDES FOR RNA VIRUS TREATMENT

The use of described compounds or pharmaceutically acceptable salts or compositions thereof for the treatment of a host infected with an RNA virus other than HCV, or other disorder more fully described herein.

Synthesis and Evaluation of 2,6-Modified Purine 2′-C-Methyl Ribonucleosides as Inhibitors of HCV Replication

A variety of 2,6-modified purine 2′-C-methylribonucleosides and their phosphoramidate prodrugs were synthesized and evaluated for inhibition of HCV RNA replication in Huh-7 cells and for cytotoxicity in various cell lines. Cellular pharmacology and HCV polymerase incorporation studies on the most potent and selective compound are reported.

SUBSTITUTED NUCLEOTIDE ANALOGS

Disclosed herein are phosphorothioate nucleotide analogs, methods of synthesizing phosphorothioate nucleotide analogs and methods of treating diseases and/or conditions such as viral infections, cancer, and/or parasitic diseases with the phosphorothioate

Dual pro-drugs of 2′-C-methyl guanosine monophosphate as potent and selective inhibitors of hepatitis C virus

We have previously reported the power of combining a 5′- phosphoramidate ProTide, phosphate pro-drug, motif with a 6-methoxy purine pro-drug entity to generate highly potent anti-HCV agents, leading to agents in clinical trial. We herein extend this work with the disclosure that a variety of alternative 6-substituents are tolerated. Several compounds exceed the potency of the prior 6-methoxy leads, and in almost every case the ProTide is several orders of magnitude more potent than the parent nucleoside. We also demonstrate that these agents act as pro-drugs of 2′-C-methyl guanosine monophosphate. We have also reported the novel use of hepatocyte cell lysate as an ex vivo model for ProTide metabolism.

NUCLEOSIDE DERIVATIVES AS INHIBITORS OF RNA-DEPENDENT RNA VIRAL POLYMERASE

The present invention provides nucleoside compounds and certain derivatives thereof which are inhibitors of RNA-dependent RNA viral polymerase. These compounds are inhibitors of RNA-dependent RNA viral replication and are useful for the treatment of RNA-d

Structure-Activity Relationship of Purine Ribonucleosides for Inhibition of Hepatitis C Virus RNA-Dependent RNA Polymerase

As part of a continued effort to identify inhibitors of hepatitis C viral (HCV) replication, we report here the synthesis and evaluation of a series of nucleoside analogues and their corresponding triphosphates. Nucleosides were evaluated for their ability to inhibit HCV RNA replication in a cell-based, subgenomic replicon system, while nucleoside triphosphates were evaluated for their ability to inhibit in vitro RNA synthesis mediated by the HCV RNA-dependent RNA polymerase, NS5B. 2′-C-Methyladenosine and 2′-C-methylguanosine were identified as potent inhibitors of HCV RNA replication, and the corresponding triphosphates were found to be potent inhibitors of HCV NS5B-mediated RNA synthesis. The data generated in the cell-based assay demonstrated a fairly stringent structure- activity relationship around the active nucleosides. Increase in steric bulk beyond methyl on C2, change in the stereo- or regiochemistry of the methyl substituent, or change of identity of the heterobase beyond that of the endogenous adenine or guanine was found to lead to loss of inhibitory activity. The results highlight the importance of the ribo configuration 2′- and 3′-hydroxy pharmacophores for inhibition of HCV RNA replication in the cell-based assay and demonstrate that inclusion of the 2′ -C-methylribonucleoside pharmacophore leads to increased resistance to adenosine deaminase and purine nucleoside phosphorylase mediated metabolism.