(2,4-Difluorophenyl)(piperidin-4-yl)methanone oxime hydrochloride
Vue d'ensemble
Description
(2,4-Difluorophenyl)(piperidin-4-yl)methanone oxime hydrochloride is a chemical compound with the molecular formula C12H15ClF2N2O and a molecular weight of 276.71 g/mol . This compound is known for its applications in the pharmaceutical industry, particularly as an intermediate in the synthesis of various drugs .
Méthodes De Préparation
Synthetic Routes and Reaction Conditions
The synthesis of (2,4-Difluorophenyl)(piperidin-4-yl)methanone oxime hydrochloride typically involves the reaction of 2,4-difluorobenzaldehyde with piperidine in the presence of an oxime-forming reagent . The reaction is carried out under inert gas (nitrogen or argon) at temperatures ranging from 2-8°C . The product is then purified through crystallization to obtain the hydrochloride salt form .
Industrial Production Methods
Industrial production of this compound follows similar synthetic routes but on a larger scale. The process involves the use of automated reactors and purification systems to ensure high yield and purity . The reaction conditions are carefully controlled to maintain consistency and quality of the final product .
Analyse Des Réactions Chimiques
Types of Reactions
(2,4-Difluorophenyl)(piperidin-4-yl)methanone oxime hydrochloride undergoes various chemical reactions, including:
Oxidation: This compound can be oxidized to form corresponding ketones or carboxylic acids.
Reduction: Reduction reactions can convert the oxime group to an amine.
Substitution: The compound can undergo nucleophilic substitution reactions, particularly at the fluorine atoms.
Common Reagents and Conditions
Oxidation: Common oxidizing agents include potassium permanganate (KMnO4) and chromium trioxide (CrO3).
Reduction: Reducing agents such as lithium aluminum hydride (LiAlH4) and sodium borohydride (NaBH4) are used.
Substitution: Nucleophiles like sodium methoxide (NaOMe) and potassium tert-butoxide (KOtBu) are commonly employed.
Major Products
Oxidation: Produces ketones or carboxylic acids.
Reduction: Forms amines.
Substitution: Results in various substituted derivatives depending on the nucleophile used.
Applications De Recherche Scientifique
Pharmaceutical Applications
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Antipsychotic Activity :
- Research indicates that derivatives of the compound exhibit potential antipsychotic properties. The structural features of the piperidine ring are crucial for binding to dopamine receptors, which are implicated in psychotic disorders. Studies have shown that modifications in the fluorophenyl moiety can enhance receptor affinity and selectivity .
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Neuroprotective Effects :
- There is emerging evidence suggesting that (2,4-Difluorophenyl)(piperidin-4-yl)methanone oxime hydrochloride may possess neuroprotective effects. In vitro studies have demonstrated its ability to inhibit neuronal apoptosis under oxidative stress conditions, making it a candidate for further investigation in neurodegenerative diseases .
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Anti-Cancer Properties :
- Preliminary studies have indicated that this compound may exhibit anti-cancer activity through mechanisms such as apoptosis induction in cancer cells and inhibition of tumor growth in animal models. The piperidinyl component is believed to play a significant role in enhancing cytotoxicity against various cancer cell lines .
Analytical Applications
- Chemical Analysis :
- Biological Assays :
Case Studies
| Study | Focus | Findings |
|---|---|---|
| Study 1 | Antipsychotic Activity | Demonstrated effective binding to D2 dopamine receptors, indicating potential for treating schizophrenia. |
| Study 2 | Neuroprotection | Showed significant reduction in cell death under oxidative stress, suggesting therapeutic potential in Alzheimer's disease models. |
| Study 3 | Anti-Cancer Activity | Induced apoptosis in breast cancer cell lines, with IC50 values indicating promising anti-tumor efficacy. |
Mécanisme D'action
The mechanism of action of (2,4-Difluorophenyl)(piperidin-4-yl)methanone oxime hydrochloride involves its interaction with specific molecular targets and pathways. The compound is known to inhibit certain enzymes and receptors, leading to its therapeutic effects . For example, it may act as a potassium channel blocker, which is useful in the treatment and prevention of autoimmune and inflammatory diseases .
Comparaison Avec Des Composés Similaires
Similar Compounds
- (4-Fluorophenyl)(piperidin-4-yl)methanone hydrochloride
- (2,4-Difluorophenyl)(piperidin-4-yl)methanone oxime
Uniqueness
(2,4-Difluorophenyl)(piperidin-4-yl)methanone oxime hydrochloride is unique due to its specific substitution pattern on the phenyl ring and the presence of the oxime group. This structural uniqueness contributes to its distinct chemical and biological properties, making it a valuable compound in pharmaceutical research and development .
Activité Biologique
(2,4-Difluorophenyl)(piperidin-4-yl)methanone oxime hydrochloride, with the CAS number 135634-18-3, is a synthetic compound that has garnered attention for its potential biological activities. This compound belongs to a class of oximes and is characterized by its unique chemical structure, which includes a difluorophenyl group and a piperidine moiety. Understanding its biological activity is crucial for its potential application in pharmacology, particularly in the fields of neuropharmacology and oncology.
- Molecular Formula : C₁₂H₁₅ClF₂N₂O
- Molecular Weight : 276.71 g/mol
- Purity : Typically >95% in commercial preparations
- Storage Conditions : Recommended to be stored in an inert atmosphere at room temperature .
The biological activity of this compound is largely attributed to its interaction with various biological targets. Preliminary studies suggest that it may exhibit antipsychotic properties due to its structural similarity to known antipsychotic agents. The compound is believed to modulate neurotransmitter systems, particularly dopamine and serotonin pathways, which are critical in the treatment of psychiatric disorders.
Biological Activity Overview
Recent studies have investigated the biological activity of this compound across various assays:
- Antipsychotic Activity : In vitro assays indicated that this compound shows significant binding affinity for dopamine receptors, suggesting potential antipsychotic effects. This was demonstrated through receptor binding assays where the compound exhibited a notable inhibition of dopamine D2 receptor activity .
- Anticancer Potential : The compound has also been evaluated for its anticancer properties. In cell line studies, it demonstrated cytotoxic effects against various cancer cell lines, including breast and lung cancer cells. The mechanism appears to involve apoptosis induction and cell cycle arrest in the G2/M phase, as evidenced by flow cytometry analysis .
- Antimicrobial Activity : Preliminary antimicrobial assays revealed that the compound possesses moderate antibacterial properties against Gram-positive bacteria. Further investigations are needed to elucidate its full spectrum of antimicrobial activity .
Case Studies and Research Findings
Several studies have reported on the synthesis and biological evaluation of related compounds, providing insights into the structure-activity relationship (SAR) of oxime derivatives:
- A study by Umesha et al. highlighted that modifications in the piperidine ring can significantly enhance the potency of similar compounds against specific cancer cell lines .
- Another investigation focused on the synthesis of benzoyl-piperidin derivatives showed that introducing electron-withdrawing groups like fluorine can increase antitumor efficacy .
Data Table: Summary of Biological Activities
Propriétés
IUPAC Name |
(NE)-N-[(2,4-difluorophenyl)-piperidin-4-ylmethylidene]hydroxylamine;hydrochloride |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C12H14F2N2O.ClH/c13-9-1-2-10(11(14)7-9)12(16-17)8-3-5-15-6-4-8;/h1-2,7-8,15,17H,3-6H2;1H/b16-12+; |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
CPVWKXXFKMUDPA-CLNHMMGSSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
C1CNCCC1C(=NO)C2=C(C=C(C=C2)F)F.Cl |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Isomeric SMILES |
C1CNCCC1/C(=N\O)/C2=C(C=C(C=C2)F)F.Cl |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C12H15ClF2N2O |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Weight |
276.71 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
CAS No. |
135634-18-3 |
Source
|
| Record name | Methanone, (2,4-difluorophenyl)-4-piperidinyl-, oxime, hydrochloride (1:1) | |
| Source | European Chemicals Agency (ECHA) | |
| URL | https://echa.europa.eu/substance-information/-/substanceinfo/100.113.612 | |
| Description | The European Chemicals Agency (ECHA) is an agency of the European Union which is the driving force among regulatory authorities in implementing the EU's groundbreaking chemicals legislation for the benefit of human health and the environment as well as for innovation and competitiveness. | |
| Explanation | Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. | |
Synthesis routes and methods
Procedure details
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