15397-12-3

Usage

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 
• 55533-86-3 3-O-Benzyl-3-C-methyl-1,2-O-isopropylidene-α-D-allofuranose 
• 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 
• 1029347-47-4 N6-tert-butanoyl-β-2'-methyl-2',3',5'-tribenzoyl-adenosine 
• 144363-85-9 6-Chloro-9-(2,3-di-O-acetyl-5-O-benzyl-2-C-methyl-β-D-ribofuranosyl)-9H-purine 
• 144363-78-0 1,2,3-Tri-O-acetyl-5-O-benzyl-2-C-methyl-D-ribofuranose 
• 144363-76-8 5-O-benzyl-2,3-di-O-isopropyliden-2-C-methylribono-γ-lactone 
• 144363-77-9 5-O-benzyl-2,3-di-O-isopropyliden-2-C-methyl-α,β-D-ribose 
• 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 

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 
• 926654-19-5 C₂₁H₂₃N₆O₇P 

Relevant academic research and scientific papers

A concise synthesis of 2'-C-methylribonucleosides

2'-C-methylribonucleosides were synthesized in five steps from commercially available 1,3,5-tri-O-benzoyl-α-D-ribose with good overall yields.

CYCLIC DINUCLEOTIDES AS STING AGONISTS

Disclosed are compounds, compositions and methods for treating of diseases, syndromes, or disorders that are affected by the modulation of STING. Such compounds are represented by Formula (I) as follows: wherein R1A, R1B, R1C, R1D, B1, R2A, R2B, R2C, R2D, and R2E are defined herein and Formula (II), wherein R1H, R1K, R1J, and R2L are defined herein.

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.

METHODS AND COMPOSITIONS FOR TREATING HEPATITIS C VIRUS

The present invention provides pharmaceutical compositions for the treatment of a hepatitis C infection in a host, comprising an antivirally effective amount of a 2'-C-branched nucleoside or a 2'-C-branched ribofuranosyl nucleoside, or pharmaceutically acceptable salts or esters thereof, in combination with one or more other anti-HCV agent. The present invention further provides the use of a 2'-C-branched nucleoside or a 2'-C-branched ribofuranosyl nucleoside, or pharmaceutically acceptable salts or esters thereof, in the manufacture of a medicament for the treatment of a hepatitis C infection in a host.

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

CHEMICAL COMPOUNDS

Phosphoramidate derivatives of nucleoside compounds derived from bases such as adenine and guanine have enhanced therapeutic potency, in particular, enhanced potency with respect to the prophylaxis or treatment of a viral infection such as hepatitis C vir

2'-C-Methyl analogues of selective adenosine receptor agonists: Synthesis and binding studies

2'-C-Methyl analogues of selective adenosine receptor agonists such as (R)-PIA, CPA, CCPA, NECA, and IB-MECA were synthesized in order to further investigate the subdomain that binds the ribose moiety. Binding affinities of these new compounds at A1

A short, flexible route toward 2'-C-branched ribonucleosides

A five-step synthesis of 2'-C-branched ribonucleosides from commercially obtained 1,3,5-tri-O-benzoyl-α-D-ribofuranose (4) is described. The free hydroxyl group of 4 was oxidized in high yield with Dess-Martin periodane reagent. The resultant 2-ketosugar was treated with MeMgBr/TiCl4, CH2=CHMgBr/CeCl3, or TMSC≡CLi/CeCl3, and in each case addition to the ketone proceeded stereoselectively to provide 2-alkylated ribofuranosides. After conversion to the corresponding tetrabenzoyl derivatives, the 2-alkylribofuranosides were coupled to nucleobases under Vorbruggen persilylation conditions, giving the β-nucleosides with high stereoselectivity. Deprotection with methanolic ammonia provided the title compounds in 17-49% overall yields from 4.

2′-C-alkylribonucleosides: Design, synthesis, and conformation

Certain 2′-C-alkylribonucleotides have been designed as potential mechanism-based inactivators of ribonucleotide reductases. A short, flexible route toward the corresponding nucleosides and NMR evidence concerning their preferred solution conformations are discussed. Copyright

New 2'-branched-chain sugar nucleoside analogs with potential antiviral or antitumor activity

The synthesis of 2'-C-hydroxymethyl and 2'-C-methyl nucleoside analogs [1-(3-deoxy-2-hydroxymethyl-D-erythro-pentofuranosyl)thymine (14), the corresponding adenine derivative. 17, 1-(2-methyl-β-D-ribofuranosyl)thymine (20) and 2'-methyladenosine (23)] by