81465-82-9 | 5-AMINO-3-(4-FLUOROPHENYL)ISOXAZOLE

CAS:81465-82-9 | 5-AMINO-3-(4-FLUOROPHENYL)ISOXAZOLE,Description

3-(4-Fluorophenyl)isoxazol-5-amine is a compound that belongs to the class of organic compounds known as isoxazoles, which are characterized by a five-membered ring containing one oxygen atom, one nitrogen atom, and three carbon atoms. The presence of a fluorophenyl group suggests that this compound may exhibit unique physical and chemical properties, potentially making it useful in various applications, including medicinal chemistry and materials science.

Synthesis Analysis

The synthesis of fluorine-substituted isoxazole derivatives can be achieved through various methods. For instance, the synthesis of 5-(4-fluorophenyl)-1H-pyrazol-3-amine, a related compound, was accomplished using a Michael addition reaction between guanidine hydrochloride and α,β-unsaturated ketones, yielding a pair of isomers with improved solubility in water or PBS buffer systems. Similarly, 5-(fluoroalkyl)isoxazole building blocks were synthesized starting from functionalized halogenoximes through a one-pot metal-free [3+2] cycloaddition, followed by late-stage deoxofluorination or nucleophilic substitution to introduce the fluoroalkyl groups. These methods highlight the versatility of synthetic approaches for incorporating fluorine atoms into isoxazole rings.

Molecular Structure Analysis

The molecular structure of isoxazole derivatives can be elucidated using various spectroscopic techniques and single-crystal X-ray diffraction. For example, the crystal structure of a pyrazole ring derivative was determined using single-crystal X-ray diffraction, and the optimized molecular structure was calculated based on density functional theory (DFT). The study of non-covalent interactions, such as hydrogen bonds and π-π interactions, is crucial for understanding the stability and reactivity of these compounds.

Chemical Reactions Analysis

Isoxazole derivatives can participate in a range of chemical reactions. The synthesis of novel Schiff bases using 2-amino-5-(3-fluoro-4-methoxyphenyl)thiophene-3-carbonitrile and 1,3-disubstituted pyrazole-4-carboxaldehydes demonstrates the reactivity of isoxazole derivatives in condensation reactions to form Schiff bases with potential antimicrobial activity. Additionally, the reductive heterocyclization of 3-(2-nitrophenyl)isoxazoles to form quinoline-4-amines showcases the ability of isoxazole rings to undergo transformation into other heterocyclic systems10 .

Physical and Chemical Properties Analysis

The physical and chemical properties of isoxazole derivatives are influenced by the presence of fluorine atoms and other substituents. The introduction of fluorine can significantly alter the compound's lipophilicity, electronic distribution, and hydrogen bonding capacity. For instance, the anti-inflammatory activity of fluorine-substituted 1,4,5,6-tetrahydrobenzo[h]quinazolin-2-amine derivatives was attributed to the presence of o- and p-fluoro substituents, which displayed potential inhibitory effects on LPS-induced NO secretion. The solubility of these compounds in aqueous media is also an important property, as demonstrated by the improved solubility of isomers in water or PBS buffer systems. Additionally, the antimicrobial activity of isoxazole derivatives can be assessed against various bacterial and fungal organisms, indicating their potential application in the development of new therapeutic agents.

Scientific Research Applications

Antibacterial and Antifungal Activity

A study by (Banpurkar, Wazalwar, & Perdih, 2018) explored the synthesis of 3-methyl-4H-isoxazol-5-one derivatives, including 4-(4-fluorophenylazo)-3-methyl-4H-isoxazol-5-one. This compound demonstrated antibacterial and antifungal properties, particularly against Staphylococcus aureus and Candida albicans.

Antitumor Activity

Research by (Potkin et al., 2014) involved the synthesis of isoxazolylcarbamides, including variants derived from 4-fluorophenol, which showed significant antitumor activities. Similarly, (Sekhar et al., 2019) synthesized 1,3,4-thiadiazole derivatives, including N-benzyl-5-(4-fluorophenyl)-1,3,4-thiadiazole-2-amines, showing promising inhibitory activities against breast cancer cell lines.

Synthesis of Novel Compounds

(Hamama, Ibrahim, & Zoorob, 2017) investigated the synthesis of new isoxazole derivatives, including compounds incorporating 4-fluorophenyl structures, which exhibited higher antitumor activity than standard cytotoxic agents in some cases.

Synthesis of Heterocyclic Compounds

(Petkevich et al., 2018) synthesized fluorine-containing derivatives of isoxazoles, focusing on the effects of fluorination on the chemical properties of these compounds.

Dual Antagonist Synthesis

A study by (LiangJimmy, Deng, & Mani, 2011) described the synthesis of a potent 5HT7/5HT2 dual antagonist using a 3-(4-fluorophenyl)-2-isopropyl-2,4,5,6,7,8-hexahydropyrazolo[3,4-d]azepine scaffold, highlighting the potential for pharmaceutical applications.

In Vitro Antibacterial Activity

(Uwabagira, Sarojini, & Poojary, 2018) synthesized N-(3-chloro-2-methylphenyl)-4-(4-fluorophenyl)-1,3-thiazol-2-amine, testing its in vitro antibacterial activity against specific bacterial strains.

Anticancer and Antitubercular Agents

(Yakantham, Sreenivasulu, & Raju, 2019) developed thiazol-4-amine derivatives with isoxazol-5-yl substituents, including 4-fluorophenyl variants, to assess their anticancer and antitubercular properties.

Antimicrobial Activity

(Kumar et al., 2019) created a series of isoxazole derivatives, incorporating 5-fluorophenyl elements, to evaluate their antimicrobial activities against various bacterial and fungal organisms.

Safety And Hazards

According to the available information, 3-(4-Fluorophenyl)isoxazol-5-amine may be harmful if swallowed (Hazard Statements H302). It is classified as Acute Tox. 4 Oral.

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