2126162-29-4 | 3-methoxy-3-(trifluoromethyl)azetidine hydrochloride

CAS:2126162-29-4 | 3-methoxy-3-(trifluoromethyl)azetidine hydrochloride,Description

Synthesis Analysis

The synthesis of azetidine derivatives with trifluoromethyl groups has been explored in the literature. For instance, 3-Hydroxy-4-(trifluoromethyl)azetidin-2-ones were synthesized from 3-benzyloxy-β-lactams and then transformed into new 3-chloro-4-(trifluoromethyl)azetidin-2-one building blocks. These building blocks serve as precursors for constructing CF3-containing aminopropanes, oxazinanes, and aziridines. The synthesis route involves the use of chlorides and intramolecular cyclization to create novel compounds with the trifluoromethyl group, which is known for its ability to enhance the metabolic stability and bioavailability of pharmaceuticals.

Molecular Structure Analysis

The molecular structure of azetidine derivatives is characterized by a four-membered ring that imparts rigidity and can influence the biological activity of the compounds. The presence of a trifluoromethyl group is particularly interesting as it can significantly affect the electronic properties of the molecule due to its strong electron-withdrawing nature. This can lead to enhanced binding affinity to biological targets and improved pharmacokinetic properties.

Chemical Reactions Analysis

Azetidine derivatives undergo various chemical reactions that are useful in synthetic chemistry. For example, the reaction of N-(ethoxycarbonyl)-3-(bromomethyl)-3-chloroazetidine with DBU leads to the formation of haloalkenes through a process known as the "halogen dance," which involves nucleophilic displacement and elimination reactions. Additionally, the synthesis of 3,3-dichloroazetidines involves the generation of 1-azaallylic carbanions, which are then reacted with aromatic aldehydes to produce beta-hydroxy imines. These imines are further converted into azetidines through cyclization reactions.

Physical and Chemical Properties Analysis

The physical and chemical properties of azetidine derivatives, such as solubility, melting point, and reactivity, are influenced by the substituents on the azetidine ring. The trifluoromethyl group, in particular, is known to increase the lipophilicity of the molecule, which can be beneficial for crossing biological membranes. The electron-withdrawing nature of the trifluoromethyl group also affects the acidity of adjacent protons, potentially leading to increased reactivity in certain chemical transformations.

Scientific Research Applications

Anticancer Potential

3-Methoxy-3-(trifluoromethyl)azetidine hydrochloride and its derivatives have shown significant potential in anticancer research. For example, a series of thiourea compounds bearing 3-(4-methoxyphenyl)azetidine moiety, which is structurally related to 3-Methoxy-3-(trifluoromethyl)azetidine, have been synthesized and evaluated for their in vitro anticancer activity against various human cancer cell lines. These compounds have shown potent anticancer properties, with some exhibiting more potency than the standard drug Doxorubicin in specific cell lines (Parmar et al., 2021).

Synthesis and Reactivity

The compound's synthesis and reactivity have been explored in various studies. For instance, research on the convenient synthesis of 3,3-dichloroazetidines, a class closely related to 3-Methoxy-3-(trifluoromethyl)azetidine, provides insights into novel methods of producing azetidine derivatives, which are crucial for further pharmaceutical applications (Aelterman et al., 1998).

Building Blocks for Other Compounds

The compound has been used as a building block for the preparation of various derivatives. For example, 3-Hydroxy-4-(trifluoromethyl)azetidin-2-ones, closely related to 3-Methoxy-3-(trifluoromethyl)azetidine, have been transformed into new building blocks for the construction of CF3-containing aminopropanes, oxazinanes, and aziridines (Dao Thi et al., 2018).

GABA Uptake Inhibitors

Azetidine derivatives, including 3-Methoxy-3-(trifluoromethyl)azetidine, have been evaluated as gamma-aminobutyric acid (GABA) uptake inhibitors. These compounds are of interest in neurological research due to their potential impact on neurotransmitter regulation (Faust et al., 2010).

Novel Therapeutic Agents

Research on azetidine derivatives has also focused on developing novel therapeutic agents. For example, the exploration of novel 3-substituted azetidine derivatives as triple reuptake inhibitors highlights the therapeutic potential of these compounds in the treatment of various conditions (Han et al., 2012).

Safety And Hazards

The compound causes skin irritation and serious eye irritation. It may also cause respiratory irritation. It’s recommended to avoid breathing dust/fume/gas/mist/vapors/spray of the compound. In case of contact with skin or eyes, it’s advised to wash with plenty of water.

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