15397-12-3

Basic information

• Product Name: 2'-C-Methyladenosine
• Synonyms: 2'-CMethyl-D-adenosine;Adenosine, 2'-C-methyl-;2'-C-Methyladenosine;6-Amino-9-(2'-C-methyl-b-D-ribofuranosyl)purine
• CAS NO: 15397-12-3
• Molecular Formula: C₁₁H₁₅N₅O₄
• Molecular Weight: 281.271
• Mol File: 15397-12-3.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 643.4±65.0 °C(Predicted)
• Appearance: /
• Density: 1.89
• PKA: 13.18±0.70(Predicted)
• CAS DataBase Reference: 2'-C-Methyladenosine(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-C-Methyladenosine(15397-12-3)
• EPA Substance Registry System: 2'-C-Methyladenosine(15397-12-3)

Safety Data

• Hazardous Substances Data: 15397-12-3(Hazardous Substances Data)

Usage

Description

2'-C-Methyladenosine is a modified nucleoside that has demonstrated the ability to inhibit Hepatitis C Virus (HCV) RNA replication without causing cytotoxicity. It is characterized by the presence of a methyl group at the 2'-C position, which contributes to its unique properties and potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
2'-C-Methyladenosine is used as an antiviral agent for its ability to inhibit HCV RNA replication. This makes it a promising candidate for the development of new treatments against Hepatitis C, a viral disease that affects the liver and can lead to severe health complications if left untreated.
Used in Research and Development:
In the field of research, 2'-C-Methyladenosine serves as a valuable tool for studying the mechanisms of HCV RNA replication and the development of novel antiviral strategies. Its potent, competitive inhibition of NS5B-catalyzed reactions in vitro provides insights into the molecular interactions involved in the viral replication process, which can be leveraged to design more effective therapeutic approaches.
Used in Drug Design and Synthesis:
The unique structure and properties of 2'-C-Methyladenosine make it an attractive starting point for the design and synthesis of new antiviral compounds. Researchers can explore modifications to its chemical structure to enhance its potency, selectivity, and pharmacokinetic properties, potentially leading to the development of more effective and safer treatments for Hepatitis C and other viral infections.

Biological Activity

2’-C-Methyladenosine is an inhibitor of hepatitis C virus (HCV) replication (IC50 = 0.3 μM in Huh-7 human hepatoma cells) that is not cytotoxic at concentrations up to 100 μM.{39652} It is converted intracellularly to adenosine triphosphate, which inhibits the RNA-dependent RNA polymerase nonstructural protein 5B (NS5B). It also inhibits growth of L. guyanensis in vitro (EC50 = 3 μM) and eradicates it when used at a concentration of 10 μM.

Synthesis

Synthesis of yfl-2'-methyl-adenosine (CHCl); N6-tert-butanoyl-/?-2'-methyl-2',3',5'-tribenzoyl-adenosine (400 mg, 0.590 mmol) was added to a solution of MeOH saturated with ammonia, and stirred at room temperature. After 12 hours the solvent was removed and the obtained solid was purified by column chromatography in gradient starting with a mixture of CHCl3/MeOH 9:1 then 8:2. The pure product was obtained as a white solid (120 mg, 0.427 mmol, 72%). δH (J6-DMSO): 8.47 (IH, s, H8-adenosine), 8.15 (IH, s, H2-adenosine), 7.30 (IH, s, NH26-adenosine), 5.95 (IH, s, Hl '-adenosine), 5.25-5.21 (3H, m, OH5' -adenosine, OH3'- adenosine, OH2' -adenosine), 4.12-4.05 (IH, d, H3 '-adenosine, J= 8.6 Hz), 3.91 (IH, m, H4'-adenosine), 3.84 (IH, m, H5' -adenosine), 3.70 (IH, m, H5' -adenosine), 0.77 (3H3 s, CH32'-adenosine); δc (4-DMSO): 156.02 (1C, C6-adenosine), 152.53 (1C, C2-adenosine), 149.01 (1C, C4-adenosine), 138.68 (1C, C8-adenosine), 118.67 (1C, C5-adenosine), 90.78 (1C, Cl '-adenosine), 82.52 (1C, C4' -adenosine), 78.46 (1C, C2'-adenosine), 71.63 (1C, C3' -adenosine), 59.47 (1C, C5 '-adenosine), 19.83 (1C, CH3-2'-adenosine). Anal. CaIc. for C11H15N5O4: C 46.97%, H 5.38%, N 24.90%. Found: C 46.67%, H 5.22%, N 24.20%.

Upstream product

• 144363-86-0 6-Chloro-9-(2,3-di-O-acetyl-2-C-methyl-β-D-ribofuranosyl)-9H-purine 
• 114475-10-4 9-(2,3-di-O-acetyl-2-C-methyl-5-O-p-methylbenzoyl-β-D-ribofuranosyl)-N₆-benzoyladenine 
• 15397-15-6 1,2,3,5-Tetra-O-benzoyl-2-C-methyl-α(β)-D-ribofuranose 
• 4005-49-6 N-benzoyladenine 
• 16434-52-9 C₃₉H₃₁N₅O₈ 
• 205171-04-6 (2R,3R,4R,5R)-5-((benzoyloxy)methyl)-2-(6-chloro-9H-purin-9-yl)-3-methyltetrahydrofuran-3,4-diyl dibenzoate 
• 87-42-3 6-chloropurine 
• 15397-15-6 1,2,3,5-tetra-O-benzoyl-2-C-methyl-β-D-ribofuranose 
• 157037-56-4 1,3,5-tri-O-benzoyl-2-oxo-α-D-erythro-pentofuranose 
• 22224-41-5 1,3,5-tri-O-benzoyl-α-D-ribofuranoside 
• 55533-86-3 3-O-Benzyl-3-C-methyl-1,2-O-isopropylidene-α-D-allofuranose 
• 110808-85-0 3-O-benzyl-1,2-O-isopropylidene-3-C-methyl-6-O-methylbenzoyl-α-D-allofuranose 
• 114952-95-3 1,3-di-O-acetyl-2-O-benzyl-2-C-methyl-5-O-p-methylbenzoyl-β-D-ribofuranose 
• 110835-69-3 1,3-di-O-acetyl-2-C-methyl-5-O-p-methylbenzoyl-β-D-ribofuranose 

Downstream Products

• 951663-21-1 C₂₃H₂₇ClN₅O₇P 
• 862189-29-5 cis-5'-O-[4-(S)-(3-chlorophenyl)-2-oxo-1,3,2-dioxaphosphorinan-2-yl]-2'-C-methyladenosine 
• 926654-00-4 C₂₀H₂₃BrN₅O₇P 
• 926654-16-2 C₂₀H₂₂F₂N₅O₇P 
• 926654-19-5 C₂₁H₂₃N₆O₇P 

Relevant articles and documents

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SUBSTITUTED NUCLEOSIDES, NUCLEOTIDES AND ANALOGS THEREOF

Disclosed herein are nucleotide analogs, methods of synthesizing nucleotide analogs and methods of treating diseases and/or conditions such as a Picornaviridae and/or Flaviviridae viral infections with one or more nucleotide analogs.

The phosphoramidate ProTide approach greatly enhances the activity of β-2′-C-methylguanosine against hepatitis C virus

β-2′-C-Methyl purines (1, 2) are known inhibitors of hepatitis C virus (HCV). We herein report the synthesis, biological and enzymatic evaluation of their 5′-phosphoramidate ProTides. Described herein are seven l-alanine phosphoramidate derivatives with v