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| Targets |
2,6-Dichloro-3-nitropyridine is used in the synthesis of HIV-1 reverse transcriptase inhibitors and hypoglycemic active thiazolidine-2,4-diones. Reverse transcriptase is a key enzyme in the HIV life cycle, converting viral RNA into DNA for integration into the host genome. Inhibitors of this enzyme are important antiretroviral drugs for the treatment of HIV/AIDS. The compound's pyridine core with chloro and nitro substituents provides a versatile scaffold for building enzyme-targeting molecules. As a synthetic intermediate, the compound itself is not a direct enzyme inhibitor but a building block for such agents.
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| ln Vitro |
As a synthetic intermediate, 2,6-Dichloro-3-nitropyridine is not typically evaluated for direct in vitro biological activity against specific molecular targets. The compound serves as a precursor for HIV-1 reverse transcriptase inhibitors and hypoglycemic agents rather than possessing intrinsic pharmacological activity. Its primary applications are in organic synthesis as a building block for drug discovery. Any biological activity observed would be incidental.
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| ln Vivo |
The compound itself is not typically evaluated for in vivo activity as it is a synthetic intermediate. HIV-1 reverse transcriptase inhibitors and thiazolidine-2,4-diones synthesized from 2,6-Dichloro-3-nitropyridine have been studied in various in vivo models. Reverse transcriptase inhibitors have shown efficacy in animal models of HIV infection, and thiazolidine-2,4-diones are known for their hypoglycemic activity in diabetic models. The in vivo pharmacological profile of the final drug molecules depends on the specific functional groups introduced.
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| Enzyme Assay |
Cell-free biochemical assays involving 2,6-Dichloro-3-nitropyridine typically focus on its use as a synthetic reagent. In organic synthesis, the compound can be used as a building block for the preparation of various pyridine derivatives. A standard protocol for nucleophilic aromatic substitution involves treating the compound with nucleophiles (e.g., amines, thiols) in the presence of a base in an appropriate solvent such as DMF or acetonitrile. The chloro groups at the 2- and 6-positions are activated toward nucleophilic attack by the electron-withdrawing nitro group at the 3-position. The nitro group can also be reduced to an amino group for further derivatization. Reactions are monitored by TLC and products are characterized by NMR and mass spectrometry.
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| Cell Assay |
Cell-based assays are not typically performed with 2,6-Dichloro-3-nitropyridine as the compound is a chemical reagent. For HIV-1 reverse transcriptase inhibitors or hypoglycemic agents synthesized from this intermediate, standard cell-based protocols would apply. For antiviral activity, HIV-infected cell lines are treated with the test compound and viral replication is measured by p24 antigen ELISA or other methods. For hypoglycemic activity, adipocyte or hepatocyte models may be used to assess glucose uptake or insulin sensitivity.
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| Animal Protocol |
In vivo studies are not typically conducted with 2,6-Dichloro-3-nitropyridine itself. For HIV-1 reverse transcriptase inhibitors synthesized using this intermediate, in vivo efficacy studies involve animal models of HIV infection (e.g., humanized mice or SIV models). For hypoglycemic thiazolidine-2,4-diones, efficacy is evaluated in rodent models of diabetes (e.g., db/db or STZ-induced diabetic mice). A typical protocol includes oral administration of the test compound, with monitoring of blood glucose levels or viral load.
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| ADME/Pharmacokinetics |
As a chemical reagent rather than a drug, comprehensive pharmacokinetic data for 2,6-Dichloro-3-nitropyridine is not available. The compound's molecular weight is 192.98 g/mol. The compound is a solid at room temperature with a melting point of 63-66°C. It is soluble in organic solvents but insoluble in water. For drug molecules synthesized from this intermediate, ADME properties depend on the final structure. The pyridine core generally confers favorable physicochemical properties for drug development.
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| Toxicity/Toxicokinetics |
Toxicological data specific to 2,6-Dichloro-3-nitropyridine is limited. As with all halogenated nitroheterocycles and chemical reagents, standard laboratory safety precautions should be observed when handling this compound. The compound may cause irritation upon skin or eye contact. For drug candidates synthesized using this intermediate, comprehensive toxicological evaluation is required as part of the drug development process.
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| Additional Infomation |
2,6-Dichloro-3-nitropyridine is a research chemical and synthetic intermediate rather than an approved pharmaceutical agent. No clinical trials or regulatory approvals exist for this compound itself. It is commercially available from various chemical suppliers for research purposes only. The compound's primary value lies in its utility as a versatile building block for the synthesis of HIV-1 reverse transcriptase inhibitors and hypoglycemic active thiazolidine-2,4-diones. The pyridine core with chloro and nitro substituents enables diverse functionalization for medicinal chemistry. The compound is also used in the synthesis of pyridyldifluoroacetates and other heterocyclic compounds.
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| Molecular Formula |
C5H2CL2N2O2
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|---|---|
| Molecular Weight |
192.99
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| Exact Mass |
191.949
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| CAS # |
16013-85-7
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| PubChem CID |
85239
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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 |
295.5±35.0 °C at 760 mmHg
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| Melting Point |
55-60 °C(lit.)
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| Flash Point |
132.5±25.9 °C
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| Vapour Pressure |
0.0±0.6 mmHg at 25°C
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| Index of Refraction |
1.603
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| LogP |
1.77
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
11
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| Complexity |
161
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=CC(=NC(=C1[N+](=O)[O-])Cl)Cl
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| InChi Key |
SHCWQWRTKPNTEM-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C5H2Cl2N2O2/c6-4-2-1-3(9(10)11)5(7)8-4/h1-2H
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| Chemical Name |
2,6-dichloro-3-nitropyridine
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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 | 5.1816 mL | 25.9081 mL | 51.8162 mL | |
| 5 mM | 1.0363 mL | 5.1816 mL | 10.3632 mL | |
| 10 mM | 0.5182 mL | 2.5908 mL | 5.1816 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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