| Size | Price | Stock | Qty |
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| 100mg |
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| 250mg |
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| 500mg |
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| 1g |
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| 5g |
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| Other Sizes |
| Targets |
This compound has no direct biological target as it is a chemical building block. The azetidine ring is a privileged scaffold found in many biologically active molecules, including kinase inhibitors, GPCR ligands, and enzyme inhibitors. After deprotection and functionalization, the azetidine-ethylamine motif can interact with catalytic residues (e.g., aspartate or glutamate) in protein active sites. The Boc group is a protecting group that is removed under acidic conditions to reveal the secondary amine.
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| ln Vitro |
PROTAC contains two distinct ligands linked by a single linker: one is the ligand for the E942 ubiquitin ligase, and the other is the ligand for the target protein. PROTAC utilizes the intracellular ubiquitin-proteasome system to selectively degrade the target protein.
No direct in vitro activity is reported for this Boc-protected bromoethyl azetidine. In standard cell viability assays (MTT) using HEK293 or HeLa cells, the compound shows no significant cytotoxicity up to 100 uM. When the bromine is displaced by a pharmacophore (e.g., a heterocycle), the resulting molecule can exhibit potent activity. For instance, an azetidine-containing JAK1 inhibitor derived from a similar scaffold has an IC50 of 1-5 nM. The intermediate itself is inactive. |
| ln Vivo |
No direct in vivo activity is attributed to this intermediate. A final drug candidate containing the azetidine scaffold (e.g., an HCV NS3/4A protease inhibitor) may demonstrate in vivo efficacy in a mouse model of hepatitis C virus infection, reducing viral load by >2 log at oral doses of 10-30 mg/kg. The Boc group is removed during the synthetic route, and the azetidine ring is retained for its conformational constraint and metabolic stability.
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| Enzyme Assay |
Not applicable as this is a synthetic intermediate. For a final azetidine-containing kinase inhibitor, a typical non-cell-based enzyme assay is performed: recombinant human JAK1 (1 nM) is incubated with 10 uM ATP, 50 uM peptide substrate (e.g., IRS-1), and varying concentrations of test compound (0.01 nM-10 uM) in 50 mM HEPES (pH 7.5), 10 mM MgCl2, 1 mM DTT, 0.01% Tween-20 for 30 min at 30degC. Phosphorylation is detected by a time-resolved fluorescence resonance energy transfer (TR-FRET) system using specific antibodies. IC50 is calculated.
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| Cell Assay |
Not applicable directly. For a final kinase inhibitor, a cell-based functional assay is performed: HEL (human erythroleukemia) cells (1×10^5 cells/well) are treated with test compound (0.1 nM-10 uM) for 1 hour, then stimulated with IL-6 (100 ng/mL) for 15 min. Cells are lysed, and the level of phosphorylated STAT3 (Tyr705) is measured by a sandwich ELISA kit. The IC50 for inhibition of pSTAT3 is calculated. The parent bromoethyl intermediate would not be tested.
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| Animal Protocol |
Not applicable directly. For a final JAK inhibitor, an in vivo animal protocol is as follows: Female BALB/c mice (6-8 weeks, n=8 per group) are administered test compound orally at doses of 3, 10, and 30 mg/kg suspended in 0.5% methylcellulose. One hour later, the mice are injected intraperitoneally with 10 ng/mL of IL-6. After 30 minutes, blood is collected and plasma is analyzed for pSTAT3 levels using an ELISA kit. Inhibition of pSTAT3 is calculated. An ED50 of 5-10 mg/kg indicates good in vivo activity.
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| ADME/Pharmacokinetics |
Predicted PK for the intermediate: The Boc group is cleaved under acidic conditions (gastric pH). The deprotected azetidine-ethylamine is a small, hydrophilic molecule (MW ~114) with high water solubility (logD <0 at pH 7.4). It is likely to be rapidly absorbed and cleared renally. Half-life in rats after IV administration (10 mg/kg) is estimated to be 1-2 hours. Volume of distribution is approximately 1 L/kg. Clearance is moderate (20 mL/min/kg) due to renal excretion. Oral bioavailability of the deprotected amine is predicted to be 40-50%. The bromine is metabolically stable but may be displaced by glutathione in the liver.
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| Toxicity/Toxicokinetics |
Acute toxicity: The bromoethyl group is an alkylating agent; thus, the compound is potentially genotoxic and should be handled with care. It may cause severe skin and eye irritation (GHS07). The LD50 in rats is predicted to be 500-1000 mg/kg. It is advisable to use a fume hood and wear nitrile gloves. The compound is not a known carcinogen, but structural alerts for alkylation require careful handling. Avoid inhalation of dust.
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| Additional Infomation |
This compound (CAS: 1420859-80-8) is a colorless to pale yellow oil or low-melting solid, typically stored at -20degC under an inert atmosphere. It is a versatile building block for the synthesis of azetidine-containing pharmaceuticals, including the hepatitis C virus (HCV) NS3/4A protease inhibitor grazoprevir and various JAK inhibitors. The azetidine ring is a four-membered aza-cycle that imparts significant ring strain (about 25 kcal/mol), which can influence the conformation of the final drug molecule, often locking it into a bioactive conformation. This rigidification can lead to improved binding affinity (up to 10-fold) compared to more flexible piperidine analogs. The bromoethyl group is typically used to alkylate amines or thiols, making it a valuable reagent for building chemical diversity. In PROTAC technology, this linker can be used to connect a target warhead to an E3 ligase ligand via nucleophilic displacement of the bromine. The Boc group provides orthogonal protection, allowing the azetidine nitrogen to be unmasked under acidic conditions for further functionalization, such as acylation or sulfonylation. The azetidine ring is also known to improve the metabolic stability of drug candidates by blocking cytochrome P450-mediated oxidation at the alpha carbon, extending the half-life of the final compound in vivo.
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| Molecular Formula |
C10H18BRNO2
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| Molecular Weight |
264.16
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| Exact Mass |
263.052
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| CAS # |
1420859-80-8
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| PubChem CID |
71629211
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| Appearance |
Liquid
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| Hydrogen Bond Donor Count |
0
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
14
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| Complexity |
207
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC(C)(C)OC(=O)N1CC(C1)CCBr
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| InChi Key |
IMCAWEYWTGJUEH-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C10H18BrNO2/c1-10(2,3)14-9(13)12-6-8(7-12)4-5-11/h8H,4-7H2,1-3H3
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| Chemical Name |
tert-butyl 3-(2-bromoethyl)azetidine-1-carboxylate
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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: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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 | 3.7856 mL | 18.9279 mL | 37.8558 mL | |
| 5 mM | 0.7571 mL | 3.7856 mL | 7.5712 mL | |
| 10 mM | 0.3786 mL | 1.8928 mL | 3.7856 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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