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 has been shown to inhibit HCV RNA replication in the absence of cytotoxicity. The corresponding triphosphates were shown to be potent, competitive inhibitors of NS5B-catalyzed reactions in vitro.

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

• 205171-04-6 (2R,3R,4R,5R)-5-((benzoyloxy)methyl)-2-(6-chloro-9H-purin-9-yl)-3-methyltetrahydrofuran-3,4-diyl dibenzoate 
• 16434-52-9 C₃₉H₃₁N₅O₈ 
• 1029347-47-4 N6-tert-butanoyl-β-2'-methyl-2',3',5'-tribenzoyl-adenosine 
• 32865-86-4 6-chloro-9-trimethylsilylpurine 
• 110808-88-3 1,2,3-tri-O-acetyl-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 
• 114952-95-3 1,3-di-O-acetyl-2-O-benzyl-2-C-methyl-5-O-p-methylbenzoyl-β-D-ribofuranose 
• 110808-85-0 3-O-benzyl-1,2-O-isopropylidene-3-C-methyl-6-O-methylbenzoyl-α-D-allofuranose 
• 55533-86-3 3-O-Benzyl-3-C-methyl-1,2-O-isopropylidene-α-D-allofuranose 
• 22224-41-5 1,3,5-tri-O-benzoyl-α-D-ribofuranoside 
• 4005-49-6 N-benzoyladenine 
• 157037-56-4 1,3,5-tri-O-benzoyl-2-oxo-α-D-erythro-pentofuranose 
• 15397-15-6 1,2,3,5-Tetra-O-benzoyl-2-C-methyl-α(β)-D-ribofuranose 
• 15397-15-6 1,2,3,5-tetra-O-benzoyl-2-C-methyl-β-D-ribofuranose 

Downstream Products

• 1390625-38-3 5'-O-(tert-butyldimethylsilyl)-N⁶-(4-methoxytrityl)-2'-C-methyladenosine 
• 1390625-39-4 5'-O-(tert-butyldimethylsilyl)-2',3'-di-O-levulinoyl-N⁶-(4-methoxytrityl)-2'-C-methyladenosine 
• 1043591-22-5 2',3'-di-O-levulinoyl-N⁶-(4-methoxytrityl)-2'-C-methyladenosine 

Relevant articles and documents

-

-

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