![2-Amino-6-chloro-9-[(2,3,5-tri-O-benzoyl-2-C-Methyl-beta-D-ribofuranosyl)]-9H-purine](/upload/1124/V75724.png)
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| Targets |
The molecular target of this compound is not the compound itself, but its deprotected form. The 2-C-methyl group is a well-established pharmacophore for non-obligate chain termination. Upon intracellular conversion to its triphosphate, the final nucleoside analog targets the active site of viral RNA-dependent RNA polymerases (e.g., HCV NS5B), inhibiting viral genome replication.
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| ln Vitro |
In vitro activity is not applicable as this compound is a synthetic building block, not a drug. Its value lies in providing access to potent antiviral agents. The 2-C-methyl-beta-D-ribofuranose sugar moiety is a key feature of several potent anti-HCV agents (e.g., Sofosbuvir). This compound is a tool to synthesize such agents, which are then tested for inhibition of viral polymerases.
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| ln Vivo |
Specific in vivo data for this building block itself is not relevant. However, the final deprotected nucleosides synthesized from it can be evaluated in vivo. For instance, anti-HCV candidates would be tested in a mouse model supporting HCV replication, where they would be administered and their effect on viral load measured. The benzoyl groups are removed before or during administration.
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| Enzyme Assay |
Cell-free assays are performed on the final deprotected nucleoside triphosphate. To assess activity against HCV, the purified NS5B polymerase is incubated with an RNA template, nucleotides, and the analog triphosphate. The inhibition of RNA synthesis is quantified by gel electrophoresis or by measuring the incorporation of radiolabeled nucleotides, allowing for the calculation of an IC50.
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| Cell Assay |
As a chemical intermediate, this compound is not used in cell-based assays. Its purpose is in organic synthesis. A typical protocol involves using it as a starting material to construct a 2'-C-methyl nucleoside analog. This involves selective deprotection of the benzoyl groups under mildly basic conditions, followed by further functionalization (e.g., to make a monophosphate prodrug).
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| Animal Protocol |
Animal studies are not performed with this intermediate. However, the final antiviral nucleoside analogs synthesized from it can be tested in vivo. For example, a candidate compound would be formulated in a vehicle like 5% DMSO, 40% PEG300, 5% Tween-80, 50% ddH2O and administered via oral gavage to mice in a model of viral infection. Viral load and liver function markers would then be assessed.
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| ADME/Pharmacokinetics |
This compound is a building block for organic synthesis, not a drug; therefore, its ADME is not characterized. Its molecular weight (677.66) and high lipophilicity (due to three benzoyl groups) are defined for use in chemical reactions, not biological systems. The benzoyl groups are expected to be cleaved by esterases in vivo if administered, but it is not administered directly.
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| Toxicity/Toxicokinetics |
The literature does not contain toxicological data for this intermediate. In chemical synthesis, standard safety precautions (gloves, goggles, lab coat, fume hood) should be used. The compound is stable as a solid at -20degC for up to three years. It is not intended for human consumption and should be handled as a potential irritant.
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| References |
[1]. Man S, et al. Potential and promising anticancer drugs from adenosine and its analogs. Drug Discov Today. 2021 Jun;26(6):1490-1500.
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| Additional Infomation |
This compound is a crucial intermediate for the synthesis of 2'-C-methyl nucleosides, a class that includes the clinically successful anti-HCV drug Sofosbuvir. The 2-C-methyl modification confers potent antiviral activity, and the benzoyl groups provide orthogonal protection during complex chemical synthesis. This building block is exclusively a preclinical research tool used in medicinal chemistry and drug discovery.
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| Molecular Formula |
C32H26CLN5O7
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| Molecular Weight |
628.03
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| Exact Mass |
627.152
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| CAS # |
641571-44-0
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| PubChem CID |
58730438
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
816.3±75.0 °C at 760 mmHg
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| Flash Point |
447.5±37.1 °C
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| Vapour Pressure |
0.0±2.9 mmHg at 25°C
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| Index of Refraction |
1.684
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| LogP |
7.85
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
11
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| Rotatable Bond Count |
11
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| Heavy Atom Count |
45
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| Complexity |
1050
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| Defined Atom Stereocenter Count |
4
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| SMILES |
ClC1C2=C(N=C(N)N=1)N(C=N2)[C@H]1[C@@](C)([C@@H]([C@@H](COC(C2C=CC=CC=2)=O)O1)OC(C1C=CC=CC=1)=O)OC(C1C=CC=CC=1)=O
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| InChi Key |
HHGHJWFDGDHDSS-ZLZVUVTQSA-N
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| InChi Code |
InChI=1S/C32H26ClN5O7/c1-32(45-29(41)21-15-9-4-10-16-21)24(44-28(40)20-13-7-3-8-14-20)22(17-42-27(39)19-11-5-2-6-12-19)43-30(32)38-18-35-23-25(33)36-31(34)37-26(23)38/h2-16,18,22,24,30H,17H2,1H3,(H2,34,36,37)/t22-,24-,30-,32-/m1/s1
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| Chemical Name |
[(2R,3R,4R,5R)-5-(2-amino-6-chloropurin-9-yl)-3,4-dibenzoyloxy-4-methyloxolan-2-yl]methyl benzoate
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.5923 mL | 7.9614 mL | 15.9228 mL | |
| 5 mM | 0.3185 mL | 1.5923 mL | 3.1846 mL | |
| 10 mM | 0.1592 mL | 0.7961 mL | 1.5923 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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