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2-Amino-6-chloropurine is a purine analog that serves as a precursor for the synthesis of various nucleoside and nucleotide analogs. As a purine derivative, the compound can interact with enzymes involved in purine metabolism, including nucleoside phosphorylases, kinases, and deaminases. The compound is used in the enzymatic synthesis of 2'-deoxyguanosine using nucleoside deoxyribosyltransferase. It serves as a substrate for the synthesis of 9-alkyl purines and phosphonomethoxypropyl derivatives of purine and pyrimidine bases. As a chlorinated purine, the compound can undergo nucleophilic substitution reactions to introduce various functional groups at the 6-position, enabling the synthesis of diverse purine derivatives. Its structural similarity to natural purines allows it to interact with purine-binding proteins and enzymes, making it valuable for studying purine metabolism and developing antiviral and anticancer agents.
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| ln Vitro |
2-Amino-6-chloropurine is a starting point for the creation of nucleotide analogs that have antiviral properties against the human herpesvirus 6 (HHV-6) and the Epstein-Barr virus (EBV). 11. (Z)- and (E)-2-((hydroxymethyl)cyclopropylidene)methyladenine and -guanine Qiu, Y.-L., Ksebati, MB, Ptak, RG, et al. New nucleotide analogs possessing wide-ranging antiviral efficacy 1998; J. Med. Chemistry 41(1): 10–23
In vitro, 2-amino-6-chloropurine is used as a substrate in enzymatic synthesis reactions. It finds its uses in the enzymatic synthesis of 2'-deoxyguanosine using nucleoside deoxyribosyltransferase-II. The compound is also used in the synthesis of 9-alkyl purines and (R)- and (S)-N-(2-phosphonomethoxypropyl) derivatives of purine and pyrimidine bases. These derivatives are important for the development of antiviral and anticancer agents. In biochemical research, the compound is used to study purine metabolism and enzyme kinetics. It serves as a precursor for the synthesis of various nucleoside analogs that can be used as substrates or inhibitors of purine-metabolizing enzymes. The compound's reactivity at the 6-chloro position allows for the introduction of various nucleophiles, enabling the synthesis of diverse purine derivatives for drug discovery. |
| ln Vivo |
In vivo activity is mediated through the derivatives of 2-amino-6-chloropurine rather than the parent compound itself. The nucleoside and nucleotide analogs synthesized from this compound may be evaluated in animal models for antiviral, anticancer, or other therapeutic activities. For example, 9-alkyl purines and phosphonomethoxypropyl derivatives of purine bases have been investigated for their antiviral properties. The compound's derivatives may target viral polymerases or other enzymes involved in nucleic acid metabolism. However, specific in vivo studies on the parent compound are limited, as it is primarily a synthetic intermediate. The parent compound itself is not typically administered in vivo due to its role as a building block rather than a pharmacological agent.
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| Enzyme Assay |
Cell-free assays involving 2-amino-6-chloropurine are focused on its use as a substrate in enzymatic synthesis reactions. Standard protocols for the enzymatic synthesis of 2'-deoxyguanosine involve incubating 2-amino-6-chloropurine with 2'-deoxyribose-1-phosphate and nucleoside deoxyribosyltransferase-II in buffer at appropriate temperature and pH. The reaction progress is monitored by HPLC or UV spectroscopy. For the synthesis of 9-alkyl purines, the compound is alkylated at the N-9 position using alkylating agents under basic conditions. For the synthesis of phosphonomethoxypropyl derivatives, the compound is reacted with appropriate phosphonate reagents. The compound's reactivity can be studied using various analytical techniques including NMR spectroscopy, mass spectrometry, and HPLC.
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| Cell Assay |
Cellular assays are not commonly performed with 2-amino-6-chloropurine itself, as it is a chemical intermediate rather than a bioactive compound. However, its derivatives, such as nucleoside analogs and phosphonomethoxypropyl derivatives, may be evaluated in cell-based systems for antiviral, anticancer, or other biological activities. For antiviral activity, derivatives are tested against virus-infected cell cultures, and viral replication is measured. For anticancer activity, derivatives are tested in cancer cell lines, and cell viability and proliferation are assessed. The parent compound itself is not used as a test article in cell-based experiments due to its primary role as a synthetic building block.
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| Animal Protocol |
Animal studies are not conducted with the parent compound 2-amino-6-chloropurine. Its derivatives, such as nucleoside analogs and phosphonomethoxypropyl derivatives, may be evaluated in animal models for therapeutic efficacy. For antiviral agents, animal models of viral infection are used to assess efficacy and safety. For anticancer agents, xenograft or orthotopic mouse models are used to assess tumor growth inhibition. The parent compound itself is not administered to animals, as it is a synthetic intermediate. Toxicity and pharmacological profiles for the parent compound are inferred from related purine derivatives.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for 2-amino-6-chloropurine are not well characterized, as the compound is primarily a synthetic intermediate rather than a drug candidate. With a molecular weight of 169.57 g/mol, the compound is small and would be expected to have moderate bioavailability if administered. The compound is soluble in 1 mol/L NaOH, suggesting that it may have limited water solubility at neutral pH. However, comprehensive pharmacokinetic studies including absorption, distribution, metabolism, and excretion have not been performed, as the compound is not intended for therapeutic use. For research purposes, the compound is typically handled as a neat chemical and not administered to living organisms for pharmacokinetic profiling. The compound's purine structure suggests that it may be metabolized by purine-metabolizing enzymes if administered.
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| Toxicity/Toxicokinetics |
Toxicological data for 2-amino-6-chloropurine are limited. The compound should be stored away from oxidizing agents and kept in a cool, dry, and well-ventilated condition. Standard safety precautions for handling halogenated heterocycles and purine derivatives apply, including the use of personal protective equipment such as gloves and safety goggles. The compound should be handled in a well-ventilated area, and contact with skin and eyes should be avoided. In case of exposure, affected areas should be rinsed thoroughly with water. The compound is not classified as a carcinogen or mutagen based on available data, but comprehensive toxicological evaluation has not been performed. As with all research chemicals, it should be handled with care and used only in accordance with safety guidelines.
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| References | |
| Additional Infomation |
6-Chloroguanine is an organochlorine compound formed by replacing the chlorine atom at the 6-position of 7H-purine-2-amine. It is a 2-aminopurine compound and also an organochlorine compound.
2-Amino-6-chloropurine is a research chemical, not an approved drug. It has no clinical trial or marketing approval status for therapeutic use. The compound is a purine derivative that finds its uses in the enzymatic synthesis of 2'-deoxyguanosine, 9-alkyl purines, and (R)- and (S)-N-(2-phosphonomethoxypropyl) derivatives of purine and pyrimidine bases. It is also known as Famciclovir Related Compound F and 6-Chloro-2-aminopurine. The compound has a molecular weight of 169.57 g/mol, a purity of >98.5% by HPLC, and appears as a white to cream or pale yellow powder. It should be stored away from oxidizing agents in a cool, dry, and well-ventilated condition. The compound is for research use only and not for human use. |
| Molecular Formula |
C5H4CLN5
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| Molecular Weight |
169.57
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| Exact Mass |
169.015
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| CAS # |
10310-21-1
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| PubChem CID |
5360349
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| Appearance |
Off-white to light yellow solid powder
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| Density |
1.8±0.1 g/cm3
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| Boiling Point |
315.2ºC at 760mmHg
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| Melting Point |
>300 °C(lit.)
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| Flash Point |
144.4ºC
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| Vapour Pressure |
1.75E-15mmHg at 25°C
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| Index of Refraction |
1.827
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| LogP |
-0.03
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
11
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| Complexity |
154
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=NC2=C(N1)C(=NC(=N2)N)Cl
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| InChi Key |
RYYIULNRIVUMTQ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C5H4ClN5/c6-3-2-4(9-1-8-2)11-5(7)10-3/h1H,(H3,7,8,9,10,11)
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| Chemical Name |
6-chloro-7H-purin-2-amine
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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 Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| 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) |
DMSO: 33.33 mg/mL (196.56 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (14.74 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.8973 mL | 29.4863 mL | 58.9727 mL | |
| 5 mM | 1.1795 mL | 5.8973 mL | 11.7945 mL | |
| 10 mM | 0.5897 mL | 2.9486 mL | 5.8973 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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