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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
Molecular Weight:
281.27
MDL Number:
MFCD02682944
MOL File:
15397-12-3.mol
Last updated:2023-05-21 10:59:17

2'-C-Methyladenosine Properties

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)

2'-C-Methyladenosine price More Price(18)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Cayman Chemical 23062 2'-C-Methyladenosine ≥98% 15397-12-3 50mg $231 2024-03-01 Buy
Cayman Chemical 23062 2'-C-Methyladenosine ≥98% 15397-12-3 100mg $436 2024-03-01 Buy
Medical Isotopes, Inc. C107863 2?-C-Methyladenosine 15397-12-3 250mg $550 2021-12-16 Buy
Biosynth Carbosynth NM07917 2'-C-Methyladenosine 15397-12-3 250mg $150 2021-12-16 Buy
AK Scientific 3659CC 2'-C-Methyladenosine 15397-12-3 100mg $164 2021-12-16 Buy
Product number Packaging Price Buy
23062 50mg $231 Buy
23062 100mg $436 Buy
C107863 250mg $550 Buy
NM07917 250mg $150 Buy
3659CC 100mg $164 Buy

2'-C-Methyladenosine Chemical Properties,Uses,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.

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_15397-12-3
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%.

205171-04-6
15397-12-3
Synthesis of 2'-C-Methyladenosine from 6-Chloro-9-(2,3,5-tri-O-benzoyl-2-C-methyl-beta-D-ribofuranosyl)-9H-purine

2'-C-Methyladenosine Preparation Products And Raw materials

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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