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| Targets |
4-Amino-2,6-dichloropyrimidine does not have a defined primary drug target as it is a synthetic intermediate rather than a therapeutic agent itself. However, derivatives synthesized from this compound have been developed to target various biological pathways. Most notably, it is used in the preparation of indoleamine 2,3-dioxygenase (IDO) inhibitors, an enzyme involved in immune regulation and cancer immunotherapy. Related pyrimidine derivatives have also been investigated for antibacterial and anticancer activities. The compound's reactivity at the 2- and 6-chloro positions and the 4-amino group allows for diverse functionalization to create molecules that interact with specific enzymes or receptors.
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| ln Vitro |
Aminochloropyrimidine is produced via Suzuki coupling 4-amino-2,6-dichloropyrimidine with 5-chloro-2-methoxyphenylboronic acid.
As a synthetic intermediate, 4-Amino-2,6-dichloropyrimidine itself is not typically evaluated for direct in vitro biological activity against specific targets. However, related 2-amino-4,6-dichloropyrimidines have demonstrated immunomodulatory effects, including inhibition of nitric oxide production in mouse peritoneal cells. Additionally, 4-amino-5-cyano-2,6-disubstituted pyrimidines synthesized from related intermediates have shown in vitro antifilarial DNA topoisomerase II inhibitory activity. The compound serves as a precursor for biologically active molecules rather than possessing intrinsic pharmacological activity. |
| ln Vivo |
The compound itself is not typically evaluated for in vivo activity as it is a synthetic intermediate. However, drug candidates derived from 4-Amino-2,6-dichloropyrimidine have been studied in various in vivo models. IDO inhibitors prepared using this intermediate have been investigated in animal models of cancer and immune disorders. Agrochemical derivatives have been tested in agricultural settings for herbicidal and pesticidal efficacy. The in vivo pharmacological profile of the final drug molecules depends on the specific functional groups and overall structure introduced during subsequent synthetic steps.
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| Enzyme Assay |
Cell-free enzyme assays for compounds derived from 4-Amino-2,6-dichloropyrimidine typically involve measuring inhibition of target enzymes such as IDO. A standard protocol includes incubating the test compound with the recombinant enzyme and substrate in appropriate buffer at 37°C for a specified duration, followed by detection of product formation via spectrophotometry or HPLC. For IDO inhibition, the production of kynurenine from tryptophan is commonly monitored at 320 nm or using colorimetric detection with p-dimethylaminobenzaldehyde. IC50 values are determined from dose-response curves using nonlinear regression analysis. Assays are performed in triplicate with appropriate positive controls.
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| Cell Assay |
Cell-based assays for evaluating compounds derived from this intermediate typically use cancer cell lines or immune cells. A standard protocol involves seeding cells in 96-well plates and treating with varying concentrations of the test compound for 24-72 hours. Cell viability is assessed using MTT or CCK-8 assays. For IDO inhibitor evaluation, cells are stimulated with IFN-γ to induce IDO expression, and kynurenine levels in culture supernatants are measured. Related pyrimidine derivatives have been tested for nitric oxide inhibition in mouse peritoneal cells. Cells are cultured in appropriate media with 10% FBS at 37°C in 5% CO₂. IC₅₀ values are calculated from dose-response curves.
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| Animal Protocol |
In vivo efficacy studies for drug candidates derived from this intermediate typically employ mouse xenograft models for anticancer evaluation or rodent models of inflammation for immunomodulatory assessment. A typical protocol involves subcutaneous implantation of tumor cells in immunocompromised mice, followed by oral or intraperitoneal administration of the test compound at various doses (e.g., 10-100 mg/kg) daily for 2-4 weeks. Tumor volume is measured twice weekly using calipers, and body weight is monitored for toxicity assessment. At study termination, tumors are excised for histopathological and biomarker analysis. For agrochemical applications, herbicidal efficacy is tested in greenhouse studies on target weed species.
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| ADME/Pharmacokinetics |
As a synthetic intermediate rather than a drug, comprehensive pharmacokinetic data for 4-Amino-2,6-dichloropyrimidine is not available. The ADME properties of final drug molecules derived from this intermediate are determined by their specific chemical structures. Generally, halogenated pyrimidines may exhibit moderate oral bioavailability and variable plasma protein binding depending on substituents. Metabolic clearance typically occurs via hepatic cytochrome P450-mediated oxidation and conjugation reactions. The compound's logP and other physicochemical properties can be estimated from its structure, but actual PK parameters require empirical determination for each derivative.
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| Toxicity/Toxicokinetics |
Toxicological data specific to 4-Amino-2,6-dichloropyrimidine as a standalone compound is limited in publicly available literature. As with all chemical intermediates, standard laboratory safety precautions should be observed when handling this compound. The final drug molecules synthesized from this intermediate undergo comprehensive toxicological evaluation including acute and repeat-dose toxicity studies in rodents and non-rodents, genotoxicity assays (Ames test, micronucleus test), and safety pharmacology assessments. The toxicity profile varies significantly depending on the final structure and should be evaluated on a case-by-case basis for each derivative.
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| Additional Infomation |
4-Amino-2,6-dichloropyrimidine is primarily a research chemical and synthetic intermediate rather than an approved drug. No clinical trials or regulatory approvals exist for this compound itself. It is commercially available from multiple suppliers for research purposes only. The compound is stable under recommended storage conditions and should be handled with appropriate personal protective equipment. Its utility lies in the diverse range of pharmacologically active compounds that can be synthesized from this versatile building block, particularly in the fields of oncology and immunology research. Researchers utilize this intermediate to explore structure-activity relationships and develop novel therapeutic agents.
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| Molecular Formula |
C4H3CL2N3
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|---|---|
| Molecular Weight |
163.99
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| Exact Mass |
162.97
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| CAS # |
10132-07-7
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| PubChem CID |
82387
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| Appearance |
Light yellow to yellow solid powder
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| Density |
1.6±0.1 g/cm3
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| Boiling Point |
323.5±22.0 °C at 760 mmHg
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| Melting Point |
258-267°C
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| Flash Point |
149.5±22.3 °C
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| Vapour Pressure |
0.0±0.7 mmHg at 25°C
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| Index of Refraction |
1.633
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| LogP |
1.52
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
9
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| Complexity |
99.8
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=C(N=C(N=C1Cl)Cl)N
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| InChi Key |
UPVBKNZVOJNQKE-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C4H3Cl2N3/c5-2-1-3(7)9-4(6)8-2/h1H,(H2,7,8,9)
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| Chemical Name |
2,6-dichloropyrimidin-4-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) |
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 | 6.0979 mL | 30.4897 mL | 60.9793 mL | |
| 5 mM | 1.2196 mL | 6.0979 mL | 12.1959 mL | |
| 10 mM | 0.6098 mL | 3.0490 mL | 6.0979 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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