ChemicalBook > CAS DataBase List > 2'-C-Methyladenosine

2'-C-Methyladenosine

Product Name
2'-C-Methyladenosine
CAS No.
15397-12-3
Chemical Name
2'-C-Methyladenosine
Synonyms
-C-Methyladenosine;2'-C-Methyladenosine;2''-C-Methyladenosine;2’-b-C-Methyladenosine;2’-β-C-Methyladenosine;2'-CMethyl-D-adenosine;Adenosine, 2'-C-methyl-;2'-C-Methyladenosine USP/EP/BP;2’-b-C-Methyladenosine, HCV and antiviral agent;6-Amino-9-(2'-C-methyl-b-D-ribofuranosyl)purine
CBNumber
CB31177964
Molecular Formula
C11H15N5O4
Formula Weight
281.27
MOL File
15397-12-3.mol
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2'-C-Methyladenosine Property

Boiling point:
643.4±65.0 °C(Predicted)
Density 
1.89
storage temp. 
Store at -20°C
solubility 
DMF: 5 mg/mL; DMSO: 20 mg/mL; PBS (pH 7.2): 10 mg/mL
form 
A crystalline solid
pka
13.18±0.70(Predicted)
color 
White to off-white
InChI
InChI=1S/C11H15N5O4/c1-11(19)7(18)5(2-17)20-10(11)16-4-15-6-8(12)13-3-14-9(6)16/h3-5,7,10,17-19H,2H2,1H3,(H2,12,13,14)/t5-,7-,10-,11-/m1/s1
InChIKey
PASOFFRBGIVJET-YRKGHMEHSA-N
SMILES
OC[C@H]1O[C@@H](N2C3C(=C(N=CN=3)N)N=C2)[C@](C)(O)[C@@H]1O
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Cayman Chemical
Product number
23062
Product name
2'-C-Methyladenosine
Purity
≥98%
Packaging
50mg
Price
$231
Updated
2024/03/01
Cayman Chemical
Product number
23062
Product name
2'-C-Methyladenosine
Purity
≥98%
Packaging
100mg
Price
$436
Updated
2024/03/01
Medical Isotopes, Inc.
Product number
C107863
Product name
2?-C-Methyladenosine
Packaging
250mg
Price
$550
Updated
2021/12/16
Biosynth Carbosynth
Product number
NM07917
Product name
2'-C-Methyladenosine
Packaging
250mg
Price
$150
Updated
2021/12/16
AK Scientific
Product number
3659CC
Product name
2'-C-Methyladenosine
Packaging
100mg
Price
$164
Updated
2021/12/16
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2'-C-Methyladenosine Chemical Properties,Usage,Production

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.

Uses

2'-C-Methyladenosine is an inhibitor of hepatitis C virus (HCV) replication. 2'-C-Methyladenosine inhibits HCV replicon and NS5B-catalyzed RNA synthesis with IC50 values of 0.3μM and 1.9 μM, respectively. 2'-C-Methyladenosine also potently inhibits LRV1 in Leishmania guyanensis (Lgy) and Leishmania braziliensis[1][2].

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%). |?H (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); |?c (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%.

in vivo

2'-C-Methyladenosine has inhibitory potency for HCV replicon in HB110A cells with an IC50 values of 0.3μM[1].
? 2'-C-Methyladenosine inhibits NS5B-catalyzed RNA synthesis with an IC50 values of 1.9 μM[1].
? 2′-C-methyladenosine potently inhibits LRV1 in Leishmania guyanensis (Lgy) and Leishmania braziliensis[2]

References

[1] Steven S Carroll, et al. Inhibition of hepatitis C virus RNA replication by 2'-modified nucleoside analogs. J Biol Chem. 2003 Apr 4;278(14):11979-84. DOI:10.1074/jbc.M210914200
[2] John I Robinson, et al. Concentration of 2'C-methyladenosine triphosphate by Leishmania guyanensis enables specific inhibition of Leishmania RNA virus 1 via its RNA polymerase. J Biol Chem. 2018 Apr 27;293(17):6460-6469. DOI:10.1074/jbc.RA117.001515

2'-C-Methyladenosine Preparation Products And Raw materials

Raw materials

Preparation Products

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2'-C-Methyladenosine Suppliers

China 68 France 1 India 3 United Kingdom 2 United States 10 USA 1 Global 85
TargetMol Chemicals Inc.
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15397-12-3, 2'-C-MethyladenosineRelated Search:

EC 3.5.4.4 5'-Deoxyadenosylcobalamin Cyclic AMP S-ADENOSYL-L-METHIONINE ADENOSINE 5'-TRIPHOSPHATASE Adenosine5'-(tetrahydrogen triphosphate), disodiuM salt, trihydrate (9CI) Vidarabine 2'-C-Methylguanosine 2'-C-Methylcytidine 2'-C-Methyladenosine

  • 6-Amino-9-(2'-C-methyl-b-D-ribofuranosyl)purine
  • 2'-CMethyl-D-adenosine
  • Adenosine, 2'-C-methyl-
  • 2'-C-Methyladenosine
  • -C-Methyladenosine
  • 2-(6-AMINOPURIN-9-YL)-5-(HYDROXYMETHYL)-3-METHYLOXOLANE-3,4-DIOL
  • (2R,3R,4R,5R)-2-(6-Amino-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol
  • 2’-β-C-Methyladenosine
  • 2'-C-Methyladenosine USP/EP/BP
  • 2’-b-C-Methyladenosine, HCV and antiviral agent
  • 2’-b-C-Methyladenosine
  • 2''-C-Methyladenosine
  • 15397-12-3