3-Ethylamino-4-methylphenol - 120-37-6

3-Ethylamino-4-methylphenol

Catalog Number: EVT-302280
CAS Number: 120-37-6
Molecular Formula: C9H13NO
Molecular Weight: 151.21 g/mol
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Product Introduction

Description

The exploration of novel compounds with potential therapeutic applications is a critical area of research in medicinal chemistry. Among such compounds, 3-Ethylamino-4-methylphenol derivatives have been synthesized and evaluated for their biological activities. This analysis focuses on two studies that have synthesized and tested compounds with a similar structure for their antioxidant, anti-inflammatory, and anticonvulsant activities.

Mechanism of Action

The first study synthesized a series of compounds, ethyl 2-(2-cyano-3-(substituted phenyl)acrylamido)-4,5-dimethylthiophene-3-carboxylates, and evaluated them for in vitro antioxidant and in vivo anti-inflammatory activities1. The antioxidant properties were assessed using three different models, which included the reduction of free radicals and the prevention of lipid peroxidation. The anti-inflammatory activity was tested using the carrageenan-induced rat paw edema model. The results indicated that compounds with phenolic substitution exhibited greater antioxidant activity, which suggests that the presence of a phenolic group may enhance the electron donation capacity, thus neutralizing free radicals more effectively.

The second study investigated the anticonvulsant activity of enaminones and their metabolites2. The compounds were synthesized and evaluated for their ability to prevent seizures in animal models. The most potent compound in this series was found to be ethyl 4-[(4-chlorophenyl)amino]-6-methyl-2-oxocyclohex-3-ene-1-carboxylate, which showed significant protection against seizures in mice and rats. The pharmacokinetic evaluation suggested that the active compound is converted into a decarboxylated analogue in the brain and urine, indicating a metabolic pathway that could be crucial for its anticonvulsant effect.

Applications in Various Fields

The compounds synthesized in the first study have shown promising antioxidant and anti-inflammatory activities, which could be beneficial in the treatment of diseases associated with oxidative stress and inflammation, such as arthritis, cardiovascular diseases, and neurodegenerative disorders1. The second study's findings on anticonvulsant activity suggest potential applications in the management of epilepsy and other seizure-related conditions2. The pharmacokinetic data also provide insights into the metabolism of these compounds, which is essential for understanding their mechanism of action and optimizing their therapeutic efficacy.

Properties

CAS Number

120-37-6

Product Name

3-Ethylamino-4-methylphenol

IUPAC Name

3-(ethylamino)-4-methylphenol

Molecular Formula

C9H13NO

Molecular Weight

151.21 g/mol

InChI

InChI=1S/C9H13NO/c1-3-10-9-6-8(11)5-4-7(9)2/h4-6,10-11H,3H2,1-2H3

InChI Key

CTGSQPRDMHCIMM-UHFFFAOYSA-N

SMILES

CCNC1=C(C=CC(=C1)O)C

Solubility

less than 0.1 mg/mL at 64° F (NTP, 1992)

Canonical SMILES

CCNC1=C(C=CC(=C1)O)C

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