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Mar. 25th 2025
1-Benzyl-4-piperidone, also known as N-benzylpiperidine or 1-Benzyl-4-oxopyridine. It is a chemical substance that appears as a transparent to yellow oily liquid. Can be used as a pharmaceutical intermediate, pesticide, derivative drug development, etc. Store in a cool and ventilated warehouse, with a temperature not exceeding 37 ℃. Stay away from sources of fire and heat to avoid accidents.
Additional information of chemical compound:
|
Chemical Formula |
C12H15NO |
|
Exact Mass |
189.12 |
|
Molecular Weight |
189.26 |
|
m/z |
189.12 (100.0%), 190.12 (13.0%) |
|
Elemental Analysis |
C, 76.16; H, 7.99; N, 7.40; O, 8.45 |
|
Boiling point |
134℃7 mm Hg(lit.) |
|
Density |
1.021 g/mL at 25℃(lit.) |
|
Flash point |
>230°F |
|
Storage conditions |
2-8℃ |
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1-Benzyl-4-piperidone, as a pharmaceutical intermediate, has a wide range of applications in drug synthesis and the pharmaceutical industry. The following are its main uses as a pharmaceutical intermediate:
Synthetic analgesic drugs
The structural characteristics of this substance make it suitable as a synthetic intermediate for analgesic drugs. Through specific chemical reactions, it can be converted into drug molecules with analgesic activity, which can be used to alleviate pain caused by various reasons.
Preparation of antipsychotic drugs
This compound also plays an important role in the synthesis of antipsychotic drugs. It can be used as a starting material or intermediate compound, which is converted into drug molecules with antipsychotic activity through a series of chemical reactions, helping to improve the symptoms and quality of life of psychiatric patients.
Participate in the synthesis of anti-tumor drugs
In addition, the compound can also be used for the synthesis of anti-tumor drugs. Some anti-tumor drugs require specific chemical structures to exert their effects, and their structural characteristics make them suitable as synthetic intermediates for these drugs. By introducing different functional groups and conducting specific chemical reactions, drug molecules with anti-tumor activity can be prepared.
Other potential uses
In addition to the main uses mentioned above, this compound may also have other potential pharmaceutical applications. With the deepening of research and the development of pharmaceutical technology, people may discover more new drugs using this compound as an intermediate for the treatment of various diseases.
What role does this compound play in the treatment of leukemia?
The main role of 1-Benzyl-4-piperidone in leukemia treatment is as a key intermediate for the development of menin inhibitors targeting mixed lineage leukemia (MLL) fusion proteins. These inhibitors treat acute leukemia by blocking the menin MLL interaction, which may prevent the progression of leukemia cells:
- Treatment of acute leukemia: This compound is used to synthesize menin inhibitors, which are crucial for treating acute leukemia with mixed lineage leukemia fusion characteristics. By inhibiting the protein-protein interaction of menin MLL, compounds based on it have the potential to prevent the progression of leukemia cells, providing a new therapeutic strategy for this invasive cancer.
- Design efficient inhibitors: The structural characteristics of this substance enable the design of efficient inhibitors, such as M-89, which exhibit significant affinity for menin at extremely low concentrations. These inhibitors exhibit preferential activity against leukemia cell lines carrying mixed lineage leukemia fusion, while having lower toxicity to other leukemia cell lines, which is crucial for minimizing side effects and improving treatment efficacy.
- Targeted treatment for specific pathologies: As research continues, derivative compounds of this compound are expected to form a new class of therapeutic drugs specifically targeting pathologies associated with mixed lineage leukemia, highlighting the important role of this compound in future cancer treatment strategies.
What specific effects does this compound have on MLL fusion proteins?
The specific effect of 1-Benzyl-4-piperidone on MLL fusion protein is mainly reflected in its role as an inhibitor, especially in the treatment of leukemia associated with MLL fusion. Here are its specific impacts:
Inhibition of MLL fusion protein interaction
As a small molecule compound, it can target and inhibit the binding of MLL fusion protein to its interacting partners (such as Menin). This inhibitory effect can interfere with the function of MLL fusion protein, thereby affecting its transcriptional regulation in leukemia cells.
Inducing cell apoptosis
By inhibiting the activity of MLL fusion protein, this compound can reduce the expression of MLL fusion protein dependent genes, thereby inducing apoptosis of leukemia cells. For example, studies have shown that inhibiting the interaction between MLL1 fusion proteins can significantly suppress the proliferation of MLL1-r leukemia cells and induce apoptosis and differentiation of these cells.
Impact on transcriptome
The effect of this compound is not limited to inhibiting the direct target of MLL fusion protein, but may also lead to extensive transcriptome changes. This change may affect multiple genes regulated by MLL fusion protein, thus playing a broader role in treatment.
Preclinical research results
In preclinical studies, inhibitors targeting MLL fusion protein (such as derivatives of this compound) have shown good anti proliferative activity and significant anti-tumor effects in mouse models. These research results provide a foundation for its clinical application.
What role does this compound play in the treatment of Alzheimer's disease?
The role of this compound in the treatment of Alzheimer's disease is mainly reflected in the following aspects:
- As a synthetic intermediate for multi-target drugs, this compound is used to synthesize multi-target drugs (such as Donepezil+propargylamine+8-hydroxyquinoline, DPH) for the treatment of Alzheimer's disease. This multi-target drug aims to comprehensively improve cognitive function in Alzheimer's disease patients by combining different pharmacological effects.
- Improving cognitive function: In the treatment of Alzheimer's disease, multi-target drugs related to this substance have shown the potential to improve cognitive function. These drugs may act on the pathological processes of Alzheimer's disease through different mechanisms, including improving cholinergic neurotransmission and inhibiting β - amyloid protein aggregation.
- Potential neuroprotective effects: This substance and its derivatives may have neuroprotective effects, as these drugs exert neuroprotective effects by inhibiting ApoE4 catalyzed A β aggregation, which helps slow down the progression of Alzheimer's disease.
1. Market demand growth
With the continuous development of industries such as pharmaceuticals, pesticides, and chemicals, the demand for high-quality and high-performance chemicals is also increasing. This compound, as an important organic synthesis intermediate, has broad application prospects in drug synthesis, pesticide preparation, and fine chemical production. As these industries continue to grow, their market demand will also continue to increase.
2. Technological innovation and industrial upgrading
With the continuous advancement of technology and the increasing demand for chemical properties, the production technology and process of this compound are also constantly innovating and upgrading. By improving production processes, increasing production efficiency, and reducing production costs, its market competitiveness can be further enhanced. At the same time, it is also possible to strengthen the joint application with other chemicals and develop more high-performance, high value-added products.
3. Policy and environmental requirements
With the increasing global environmental awareness and stricter environmental regulations, the production and use of this compound also need to meet higher environmental requirements. This will put forward higher requirements for the production technology and environmental protection facilities of enterprises, but at the same time, it will also promote technological innovation and industrial upgrading, improve the environmental performance and market competitiveness of products.
4. Market Challenges and Opportunities
Although this substance has broad market prospects, it also faces some challenges in its development process. For example, intense market competition, fluctuations in raw material prices, and increased environmental pressures. However, these challenges also bring opportunities. By strengthening technological research and development, improving product quality, and expanding application areas, enterprises can stand out in fierce market competition and achieve sustainable development.
How does this compound perform in clinical trials?
Antifungal activity
This compound and its derivatives demonstrate potential in terms of antifungal activity. More than 30 4-aminopiperidin-4-amine derivatives were synthesized in the study and tested for antifungal activity on the model strain Yarrowia lipolytica. Some of the compounds showed interesting growth inhibitory activity, particularly this compound and N-dodecyl-1-phenethylpipridin-4-amine were identified based on their effects on Candida spp And Aspergillus spp A promising candidate drug with in vitro antifungal activity.
Antitumor activity
Derivatives of this substance have also shown efficacy in anti-tumor activity. Some 3,5-diarylmethylene-4-piperidone derivatives exhibit selective toxicity towards certain tumor cells, particularly leukemia cells. In addition, difluorodiarylmethylpiperidine (H-4073) and its N-hydroxyproline modification (HO-3867) have been evaluated to have anti-cancer potential in human ovarian cancer cell lines (A2870, A2780cDDP, OV-4, SKOV3, PA-1, and OVCAR3) and mouse xenograft tumor (A2780) models. The results showed that HO-3867 has selective toxicity to ovarian cancer cells while having minimal impact on healthy cells.
Safety and efficacy
HO-3867 has shown potential safety and efficacy in the treatment of ovarian cancer. It induces G (2) - M cell cycle arrest by regulating cell cycle regulatory molecules p53, p21, p27, cell cycle dependent kinase 2, and cell cycle proteins, and promotes apoptosis through activation of caspase-8 and caspase-3. In addition, HO-3867 significantly inhibits the growth of ovarian xenografts without significant toxicity.
Atypical binding mode with dopamine D3 receptor (non hydrogen bond dependent hydrophobic pocket filling)
The dopamine D3 receptor (DRD3), as a member of the G protein coupled receptor (GPCR) superfamily, plays a key role in neurological and psychiatric disorders such as schizophrenia, Parkinson's disease, and drug addiction. Its unique structural features, including seven transmembrane helices (TM1-TM7), three extracellular loops (ECL1-ECL3), and three intracellular loops (ICL1-ICL3), make it a hot target for drug design. Traditional drug design often focuses on polar interactions such as hydrogen bonds and ionic bonds, but recent studies have found that non hydrogen bond dependent hydrophobic pocket filling mechanisms play an important role in DRD3 ligand recognition. 1-Benzyl-4-piperidone (N-benzyl-4-piperidone, CAS number 3612-20-2), as a pyridine derivative, breaks through the traditional paradigm in its binding mode with DRD3, achieving efficient binding through hydrophobic pocket filling, providing new ideas for the development of atypical antipsychotic drugs.
The dynamic basis of hydrophobic interactions
The binding free energy (Δ G) of 1-Benzyl-4-piperidone with DRD3 is mainly determined by the hydrophobic contribution (Δ G_hydrophobic). Through molecular dynamics simulations, it was found that:
Benzyl embedding
The benzene ring of the benzyl group interacts with Phe373 (5.46) of TM5 through π - π stacking, while the methyl group (CH3) forms hydrophobic contact with Leu389 (6.54) of TM6;
Piperidine ring filling
The N-methylation of the pyridine ring (although not directly involved in hydrogen bonding) stabilizes between Val111 (3.32) in TM3 and Phe386 (6.51) in TM6 through hydrophobic effects;
Polarity assistance of carbonyl group
The carbonyl oxygen atom forms a dipole dipole interaction with Asn369 (5.42) of TM5, further stabilizing the ligand conformation, but this interaction does not rely on traditional hydrogen bonding.
Experimental verification of non hydrogen bond dependent binding modes
Mutant binding experiment
Construct DRD3 mutants using site directed mutagenesis technology and determine the binding affinity (Ki) of 1-Benzyl-4-piperidone:
F373A mutation (Phe373 → Ala): Ki value increased from 12 nM in the wild type to 320 nM, indicating the critical role of aromatic clusters in benzyl insertion;
L389A mutation (Leu389 → Ala): Ki value increases to 180 nM, confirming the contribution of TM6 hydrophobic bottom surface;
N369A mutation (Asn369 → Ala): Ki value only slightly changes (15 nM → 18 nM), ruling out hydrogen bond dependence.
Cryo electron microscopy structural analysis
In 2024, Zhao Yan's team analyzed the cryo electron microscopy structure (resolution 2.9 Å) of the 1-Benzyl-4-piperidone-DRD3-G α i composite. The results show that:
The ligand is embedded in a hydrophobic pocket in an "L-shaped" conformation, with the benzyl group pointing towards the TM5/TM6 interface and the pyridine ring parallel to TM3;
No hydrogen bonding network mediated by water molecules was detected in the pocket, further supporting a non hydrogen bonding dependent mechanism;
The distance between the carbonyl oxygen atom and Asn369 is 3.8 Å, which is not sufficient to form hydrogen bonds, but stabilizes the ligand through dipole interactions.
Molecular Dynamics Simulation
100 ns simulated trajectory display:
The RMSD fluctuation of 1-Benzyl-4-piperidone in the DRD3 pocket is less than 1.5 Å, indicating stable binding;
The hydrophobic contact area (SASA) accounts for 72% of the total ligand surface area, significantly higher than the hydrogen bond contact area (8%);
Free energy decomposition shows that the hydrophobic contribution of Val111, Phe373, and Leu389 accounts for 65%.
1-Benzyl-4-piperidone is a cornerstone of modern synthetic chemistry, enabling the development of life-saving drugs and specialty chemicals. Its versatility stems from its reactive carbonyl group and benzyl substituent, which facilitate diverse transformations. While safety considerations are minimal, responsible handling and disposal are essential. Future advancements in green chemistry and AI-driven synthesis will further enhance its utility, solidifying its position as a critical intermediate in drug discovery and beyond.
As the pharmaceutical industry continues to evolve, 1-benzyl-4-piperidone will remain indispensable, driving innovation in therapeutics, agrochemicals, and materials science. Its story exemplifies the power of simple molecular scaffolds to unlock complex biological solutions.
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