640725-74-2

Basic information

• Product Name: 2-AMino-6-chloro-9-(2-C-Methyl-β-D-ribofuranosyl)-9H-purine
• Synonyms: 2-AMino-6-chloro-9-(2-C-Methyl-β-D-ribofuranosyl)-9H-purine;6-Chloro-9-(2-C-methyl-beta-D-ribofuranosyl)-9H-purin-2-amine;(2R,3R,4R,5R)-2-(2-AMINO-6-CHLORO-9H-PURIN-9-YL)-5-(HYDROXYMETHYL)-3-METHYLTETRAHYDROFURAN-3,4-DIOL
• CAS NO: 640725-74-2
• Molecular Formula: C₁₁H₁₄ClN₅O₄
• Molecular Weight: 315.71296
• Mol File: 640725-74-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 695.3±65.0 °C(Predicted)
• Appearance: /
• Density: 1.99±0.1 g/cm3(Predicted)
• PKA: 13.11±0.70(Predicted)
• CAS DataBase Reference: 2-AMino-6-chloro-9-(2-C-Methyl-β-D-ribofuranosyl)-9H-purine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMino-6-chloro-9-(2-C-Methyl-β-D-ribofuranosyl)-9H-purine(640725-74-2)
• EPA Substance Registry System: 2-AMino-6-chloro-9-(2-C-Methyl-β-D-ribofuranosyl)-9H-purine(640725-74-2)

Safety Data

• Hazardous Substances Data: 640725-74-2(Hazardous Substances Data)

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

• 640725-73-1 (2R,3R,4R,5R)-2-(2,6-diamino-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol 
• 374750-30-8 2'-C-methylguanosine 
• 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 
• 1422526-26-8 C₂₉H₄₀N₉O₁₀P 
• 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 
• 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 
• 1412427-38-3 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 
• 1412427-32-7 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 

Relevant articles and documents

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

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.

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.