![molecular formula C12H15NO4 B1200448 4-[(4-Methoxybenzoyl)amino]butansäure CAS No. 72432-14-5](/img/structure/B1200448.png)
4-[(4-Methoxybenzoyl)amino]butansäure
Übersicht
Beschreibung
Wissenschaftliche Forschungsanwendungen
Organic Synthesis
4-[(4-methoxyphenyl)formamido]butanoic acid serves as a versatile building block in organic chemistry. Its functional groups allow for various chemical reactions, including:
- Oxidation : Adding oxygen or removing hydrogen.
- Reduction : Adding hydrogen or removing oxygen.
- Substitution : Replacing one functional group with another.
These reactions enable the synthesis of more complex molecules, making it valuable in the development of pharmaceuticals and other chemical products.
Research indicates that this compound exhibits several biological activities:
- Antimicrobial Properties : Preliminary studies suggest potential effectiveness against various microbial strains.
- Antioxidant Activity : It may protect cells from oxidative stress, relevant in neurodegenerative disease contexts.
- Enzyme Modulation : The compound may act as an inhibitor or activator of specific enzymes, influencing metabolic pathways crucial for cellular functions.
Medicinal Chemistry
The therapeutic potential of 4-[(4-methoxyphenyl)formamido]butanoic acid is under investigation for various diseases:
- Neurological Disorders : Its ability to modulate GABA (gamma-Aminobutyric acid) transporters suggests potential applications in treating conditions like epilepsy and anxiety disorders .
- Metabolic Disorders : Studies are ongoing to evaluate its role in metabolic regulation and as a possible treatment for related diseases.
Case Studies
Several case studies have highlighted the compound's effectiveness in different applications:
- Proteomics Research : Utilized to study protein interactions and functions, demonstrating its influence on protein dynamics.
- Enzyme Inhibition Studies : Initial findings indicate that it can inhibit key metabolic enzymes, paving the way for therapeutic applications in metabolic disorders.
- Antioxidant Assays : Showed protective effects against oxidative stress, suggesting relevance in research focused on neurodegenerative diseases.
Vorbereitungsmethoden
The synthesis of 4-[(4-methoxyphenyl)formamido]butanoic acid typically involves the reaction of 4-methoxybenzoic acid with butanoic acid derivatives under specific conditions . The reaction conditions often include the use of catalysts and solvents to facilitate the formation of the desired product . Industrial production methods may involve large-scale synthesis using optimized reaction conditions to ensure high yield and purity .
Analyse Chemischer Reaktionen
4-[(4-methoxyphenyl)formamido]butanoic acid undergoes various chemical reactions, including:
Oxidation: This reaction involves the addition of oxygen or the removal of hydrogen.
Reduction: This reaction involves the addition of hydrogen or the removal of oxygen.
Substitution: This reaction involves the replacement of one functional group with another.
The major products formed from these reactions depend on the specific reagents and conditions used .
Wirkmechanismus
The mechanism of action of 4-[(4-methoxyphenyl)formamido]butanoic acid involves its interaction with specific molecular targets and pathways. It may act as an inhibitor or activator of certain enzymes or proteins, thereby modulating their activity and function . The exact molecular targets and pathways involved depend on the specific application and context of its use .
Vergleich Mit ähnlichen Verbindungen
4-[(4-methoxyphenyl)formamido]butanoic acid can be compared with other similar compounds, such as:
4-[(4-Methoxybenzoyl)amino]pentanoic acid: This compound has a similar structure but with an additional carbon atom in the butanoic acid chain.
4-[(4-Methoxybenzoyl)amino]hexanoic acid: This compound has two additional carbon atoms in the butanoic acid chain.
The uniqueness of 4-[(4-methoxyphenyl)formamido]butanoic acid lies in its specific structure and properties, which make it suitable for certain applications that other similar compounds may not be as effective for .
Biologische Aktivität
4-[(4-Methoxyphenyl)formamido]butanoic acid, with the CAS number 72432-14-5, is a compound of interest in biological research due to its potential applications in proteomics and enzyme modulation. This article explores its biological activity, mechanisms of action, and relevant case studies.
Chemical Structure and Properties
The compound is characterized by the following structural formula:
Molecular Structure:
- IUPAC Name: 4-[(4-methoxyphenyl)formamido]butanoic acid
- InChI Key: DZTVZKSCFQIBMV-UHFFFAOYSA-N
4-[(4-Methoxyphenyl)formamido]butanoic acid functions primarily through its interaction with specific enzymes and proteins. It may act as an inhibitor or activator, modulating their activity and influencing various biological pathways. Preliminary studies suggest that it may affect protein interactions crucial for cellular functions .
1. Proteomics Research
The compound is utilized in proteomics to study protein interactions and functions. Its ability to influence protein dynamics makes it a valuable tool in understanding cellular mechanisms.
2. Enzyme Inhibition
Research indicates that 4-[(4-Methoxyphenyl)formamido]butanoic acid can inhibit certain enzymes that are pivotal for metabolic processes. The exact enzymes targeted are still under investigation, but initial findings suggest potential applications in metabolic disorder treatments.
3. Antioxidant Activity
Preliminary assays have shown that this compound exhibits antioxidant properties, which may contribute to its protective effects against oxidative stress in cells. This aspect is particularly relevant in the context of neurodegenerative diseases .
Case Studies
Several studies have explored the biological activity of 4-[(4-Methoxyphenyl)formamido]butanoic acid:
Comparison with Similar Compounds
The unique structure of 4-[(4-Methoxyphenyl)formamido]butanoic acid distinguishes it from other similar compounds such as:
| Compound | Structure | Biological Activity |
|---|---|---|
| 4-[(4-Methoxybenzoyl)amino]pentanoic acid | Similar with additional carbon | Less effective in proteomics applications. |
| 4-[(4-Methoxybenzoyl)amino]hexanoic acid | Longer carbon chain | Different pharmacokinetics; less focus on enzyme inhibition. |
Future Directions
Research into 4-[(4-Methoxyphenyl)formamido]butanoic acid is ongoing, with a focus on:
- Detailed Mechanistic Studies: Understanding the specific molecular pathways affected by this compound.
- Therapeutic Applications: Exploring its potential use in treating metabolic disorders and neurodegenerative diseases.
- Formulation Development: Investigating optimal formulations for enhanced bioavailability and efficacy.
Eigenschaften
IUPAC Name |
4-[(4-methoxybenzoyl)amino]butanoic acid |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C12H15NO4/c1-17-10-6-4-9(5-7-10)12(16)13-8-2-3-11(14)15/h4-7H,2-3,8H2,1H3,(H,13,16)(H,14,15) |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
DZTVZKSCFQIBMV-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
COC1=CC=C(C=C1)C(=O)NCCCC(=O)O |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C12H15NO4 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID60222721 |
Source
|
| Record name | N-anisoyl-GABA | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID60222721 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
237.25 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
CAS No. |
72432-14-5 |
Source
|
| Record name | 4-p-Anisamidobutyric acid | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=72432-14-5 | |
| Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
| Explanation | The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated. | |
| Record name | N-Anisoyl-GABA | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0072432145 | |
| Description | ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. | |
| Record name | N-anisoyl-GABA | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID60222721 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Synthesis routes and methods
Procedure details
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