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| Targets |
4-Cyanobenzeneboronic acid is a precursor in the synthesis of various enzyme inhibitors, including Tpl2 kinase inhibitors and P2X7 antagonists. Tpl2 (tumor progression locus 2) is a serine/threonine kinase involved in the MAPK signaling pathway, and its inhibitors are being investigated for the treatment of inflammatory diseases and cancer. P2X7 is a purinergic receptor involved in inflammatory responses and pain signaling, and its antagonists are being explored for the treatment of chronic pain and inflammatory conditions. The compound has also been identified as a potential inhibitor of fatty acid amide hydrolase (FAAH), an enzyme that degrades endocannabinoids such as anandamide. Inhibition of FAAH is being investigated for the treatment of pain, anxiety, and inflammatory disorders. The compound's boronic acid group allows it to interact with various biological targets through reversible covalent bonding with diols and other nucleophilic groups.
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| ln Vitro |
In vitro, 4-cyanobenzeneboronic acid is used in Suzuki-Miyaura cross-coupling reactions. It is involved in oxidative hydroxylation and 1,4-addition reactions. The compound serves as a precursor in the synthesis of inhibitors such as Tpl2 kinase inhibitors and P2X7 antagonists. In medicinal chemistry, it is used as a building block for constructing biologically active molecules. The compound's cyano group provides additional reactivity for further functionalization, enabling the synthesis of various derivatives with enhanced biological activity. It is also used as a sulfonylation reagent for organic synthesis and drug discovery. In biochemical research, it is used to study enzyme inhibition mechanisms and as a probe for studying protein-ligand interactions.
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| ln Vivo |
In vivo activity is mediated through the derivatives of 4-cyanobenzeneboronic acid, such as Tpl2 kinase inhibitors and P2X7 antagonists, rather than the parent compound itself. Tpl2 kinase inhibitors are evaluated in animal models of inflammatory diseases and cancer. P2X7 antagonists are evaluated in animal models of chronic pain and inflammatory conditions. FAAH inhibitors synthesized from this compound are evaluated in animal models of pain, anxiety, and inflammation. In these studies, parameters such as pain threshold, inflammatory markers, and behavioral responses are assessed. The parent compound itself is not administered in vivo, as it is a synthetic intermediate rather than a pharmacological agent.
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| Enzyme Assay |
Cell-free assays involving 4-cyanobenzeneboronic acid include standard Suzuki-Miyaura coupling protocols: the compound is mixed with an aryl halide, a palladium catalyst, a base, and a solvent at appropriate temperatures under inert atmosphere. The reaction progress is monitored by TLC or HPLC. For studying enzyme inhibition, the compound or its derivatives are incubated with target enzymes (e.g., Tpl2 kinase, P2X7, FAAH) in buffer solutions, and enzymatic activity is measured using appropriate substrates. Binding affinity can be determined using surface plasmon resonance or isothermal titration calorimetry. The compound's boronic acid group allows it to form reversible covalent bonds with serine or threonine residues in enzyme active sites, making it a valuable tool for studying enzyme inhibition mechanisms.
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| Cell Assay |
Cellular assays are not performed with the parent compound 4-cyanobenzeneboronic acid. Instead, its derivatives, such as Tpl2 kinase inhibitors, P2X7 antagonists, and FAAH inhibitors, are evaluated in cell-based systems. For Tpl2 kinase inhibitors, cancer cell lines or inflammatory cell models are treated with the derivatives, and cell viability, proliferation, and MAPK pathway phosphorylation are measured. For P2X7 antagonists, immune cells or neuronal cells are treated with the derivatives, and calcium flux or cytokine release is measured. For FAAH inhibitors, cells expressing FAAH are treated with the derivatives, and endocannabinoid levels are measured. The parent compound itself is not used as a test article in cell-based experiments.
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| Animal Protocol |
Animal studies are not conducted with the parent compound 4-cyanobenzeneboronic acid. Its derivatives, including Tpl2 kinase inhibitors, P2X7 antagonists, and FAAH inhibitors, are evaluated in animal models. For Tpl2 kinase inhibitors, mouse models of inflammation or cancer are used, and tumor growth or inflammatory markers are assessed. For P2X7 antagonists, rodent models of chronic pain are used, and pain thresholds are measured. For FAAH inhibitors, animal models of pain, anxiety, and inflammation are used, and behavioral and biochemical parameters are assessed. The parent compound itself is not administered to animals.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for 4-cyanobenzeneboronic acid are not well characterized. As a boronic acid with a molecular weight of 146.94 g/mol, it may undergo rapid clearance and metabolism in biological systems. The compound is soluble in DMSO at 48 mg/mL, indicating moderate solubility in organic solvents. 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.
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| Toxicity/Toxicokinetics |
Toxicological data for 4-cyanobenzeneboronic acid are limited. The compound should be handled with appropriate safety precautions, including the use of personal protective equipment such as gloves and safety goggles. It 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. The compound is a controlled substance and may have restrictions on sale in certain territories. As with all research chemicals, it should be handled with care and used only in accordance with safety guidelines.
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| Additional Infomation |
4-Cyanobenzeneboronic acid is a research chemical, not an approved drug. It has no clinical trial or marketing approval status for therapeutic use. The compound is a boronic acid derivative used in Suzuki-Miyaura cross-coupling reactions. It is involved in oxidative hydroxylation and 1,4-addition reactions and serves as a precursor in the synthesis of Tpl2 kinase inhibitors and P2X7 antagonists. It has been identified as a potential inhibitor of fatty acid amide hydrolase (FAAH). The compound is soluble in DMSO at 48 mg/mL and should be stored at -20°C for long-term stability. It is supplied as a white to off-white solid and is used as a high-purity biochemical reagent for life science research and organic synthesis. Appropriate safety precautions should be taken when handling the compound.
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| Molecular Formula |
C7H6BNO2
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| Molecular Weight |
146.94
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| Exact Mass |
147.049
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| CAS # |
126747-14-6
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| PubChem CID |
2734326
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
355.9±44.0 °C at 760 mmHg
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| Melting Point |
>350 °C(lit.)
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| Flash Point |
169.0±28.4 °C
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| Vapour Pressure |
0.0±0.8 mmHg at 25°C
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| Index of Refraction |
1.560
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| LogP |
1.03
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
11
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| Complexity |
167
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O([H])B(C1C([H])=C([H])C(C#N)=C([H])C=1[H])O[H]
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| InChi Key |
CEBAHYWORUOILU-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C7H6BNO2/c9-5-6-1-3-7(4-2-6)8(10)11/h1-4,10-11H
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| Chemical Name |
(4-cyanophenyl)boronic acid
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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) |
DMSO: 48 mg/mL (326.66 mM)
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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 | 6.8055 mL | 34.0275 mL | 68.0550 mL | |
| 5 mM | 1.3611 mL | 6.8055 mL | 13.6110 mL | |
| 10 mM | 0.6805 mL | 3.4027 mL | 6.8055 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.
Link: https://clinicaltrials.gov/ct2/show/NCT05580042
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