374750-30-8

Basic information

• Product Name: 2'-C-Methylguanosine
• Synonyms: 2'-C-Methylguanosine;-C-Methylguanosine;2'-C-beta-Methylguanosine;2-AMino-9-((2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxyMethyl)-3-Methyltetrahydrofuran-2-yl)-1H-purin-6(9H)-one;2-C′-MeG
• CAS NO: 374750-30-8
• Molecular Formula: C₁₁H₁₅N₅O₅
• Molecular Weight: 297.27
• Product Categories: Bases & Related Reagents;Carbohydrates & Derivatives;Heterocycles;Nucleotides
• Mol File: 374750-30-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 733.108 °C at 760 mmHg
• Flash Point: 397.17 °C
• Appearance: white to beige/
• Density: 2.03
• Storage Temp.: ?20°C
• Solubility: H2O: soluble5mg/mL, clear (warmed)
• PKA: 13.31±0.70(Predicted)
• CAS DataBase Reference: 2'-C-Methylguanosine(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-C-Methylguanosine(374750-30-8)
• EPA Substance Registry System: 2'-C-Methylguanosine(374750-30-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 374750-30-8(Hazardous Substances Data)

Usage

Description

2'-C-Methylguanosine is a nucleoside derivative that possesses antiviral, antitumor, and antidiabetic properties. It serves as a prodrug agent, which can be further developed and utilized in various pharmaceutical applications.

Uses

Used in Pharmaceutical Industry:
2'-C-Methylguanosine is used as an antiviral agent for its activity against the hepatitis C virus (HCV). It functions as an intermediate in the synthesis of the novel double prodrug INX-08189, which is a new clinical candidate specifically targeting HCV.
Additionally, 2'-C-Methylguanosine is utilized as an antitumor agent, indicating its potential role in the development of cancer treatments. Its antidiabetic properties also suggest that it could be employed in the creation of drugs for the management of diabetes.

Upstream product

• 640725-74-2 (2R,3R,4R,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol 
• 890131-90-5 N²-acetyl-2',3',5'-tri-O-benzoyl-2'-C-β-methylguanosine 
• 19962-37-9 N-(6-oxo-6,9-dihydro-1H-purin-2-yl)acetamide 
• 10310-21-1 2-Amino-6-chloropurin 
• 641571-44-0 (2R,3R,4R,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-5-(benzoyloxymethyl)-3-methyltetrahydrofuran-3,4-diyl dibenzoate 
• 1188418-36-1 3-(β-D-2-C-methylribofuranosyl)-3,9-dihydro-6-(4-methoxyphenyl)-9-oxo-5H-imidazo-[1,2-a]purine 
• 1188418-39-4 3-(β-D-2-C-methylribofuranosyl)-3,9-dihydro-6-(2-thienyl)-9-oxo-5H-imidazo-[1,2-a]purine 

Downstream Products

• 1036915-06-6 C₃₇H₄₂N₅O₉PS 
• 1188418-38-3 3-(β-D-2-C-methylribofuranosyl)-3,9-dihydro-6-(4-(dimethylamino)phenyl)-9-oxo-5H-imidazo-[1,2-a]purine 
• 1188418-36-1 3-(β-D-2-C-methylribofuranosyl)-3,9-dihydro-6-(4-methoxyphenyl)-9-oxo-5H-imidazo-[1,2-a]purine 
• 1188418-37-2 3-(β-D-2-C-methylribofuranosyl)-3,9-dihydro-6-(4-(diethylamino)phenyl)-9-oxo-5H-imidazo-[1,2-a]purine 
• 1365634-76-9 2'-C-methylguanosine 5'-(O-phenyl-N-(S)-1-(cyclohexoxycarbonyl)ethyl)thiophosphoramidate 
• 1401699-49-7 N-[(4-methoxyphenyl)(diphenyl)methyl]-2’-C-methylguanosine 
• 1447583-90-5 2(R)-(2-amino-6-hydroxy-9(H)-purinyl)-4(R)-(4(S)-(3,5-difluorophenyl)-2-oxo-1,3,2-dioxaphosphorinan-2-(R)-yloxymethyl)-1(R)-methyl-7-oxo-3,6,8-trioxa-cis-bicyclo[3.3.0]octane 
• 1447583-91-6 2(R)-(2-amino-6-hydroxy-9(H)-purinyl)-4(R)-tert-butyldiphenylsilyloxymethyl-1(R)-methyl-7-oxo-3,6,8-trioxa-cis-bicyclo[3.3.0]octane 
• 1449760-07-9 5'-O-(tert-butyldimethylsilyl)-N²-(4-methoxytrityl)-3'-O-benzoyl-2'-C-methylguanosine 
• 1390625-40-7 5'-O-(tert-butyldimethylsilyl)-N²-(4-methoxytrityl)-2'-C-methylguanosine 
• 1390625-54-3 5'-O-(tert-butyldimethylsilyl)-N²-(4-methoxytrityl)-2'-C-methylguanosine 
• 1390625-55-4 N²-(4-methoxytrityl)-3'-O-benzoyl-2'-C-methylguanosine 
• 1036915-08-8 IDX 184 

Relevant articles and documents

Synthesis, antiviral activity, and stability of nucleoside analogs containing tricyclic bases

A series of 3,9-dihydro-9-oxo-5H-imidazo[1,2-A]purine nucleosides (tricylic nucleosides) were synthesized from 9-[4-α-(hydroxymethyl)cyclopent-2-ene-1-α-yl]guanine (CBV) 5, (-)-β-D-(2R,4R)-1,3-dioxolane-guanosine (DXG) 6, 3′-azido-3′-deoxy-guanosine (AZG)

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

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.