1-(4-Fluorophenyl)piperazine
1-(4-Fluorophenyl)piperazine is an important pharmaceutical intermediate that plays a key role in the synthesis of many CNS (central nervous system) drugs. It is widely used in the preparation of selective serotonin reuptake inhibitors (SSRIs) and other antidepressants. The 4-fluorophenyl moiety enhances the binding affinity of drug molecules to their target receptors, improving efficacy while reducing side effects.
It is also a core building block for the synthesis of anxiolytics and antipsychotic drugs. Through substitution, coupling, and other chemical modifications, it can generate a wide variety of structurally diverse active compounds, providing a rich platform for new drug discovery.
Key Role in Pharmaceutical Chemistry
In medicinal chemistry, the value of 1-(4-fluorophenyl)piperazine lies in its ability to provide a specific pharmacophore. The piperazine ring, a nitrogen-containing heterocycle, is capable of interacting with biological targets such as receptors and enzymes. When linked to a substituted phenyl ring such as p-fluorophenyl, the resulting fragment is widely used to design and optimize drug molecules by tuning biological activity, metabolic stability, and solubility.
Typical applications include its use as an intermediate for the antipsychotic drug Fananserin, as well as a key building block for antidepressants and other CNS drugs. It has also shown significant potential in anticancer drug research.
Fananserin (RP-62203)
Fananserin is a compound that was investigated as a dual antagonist of serotonin 5-HT₂ receptors and dopamine D₄ receptors.
Mechanism of Action & Pharmacological Properties
Fananserin exerts its pharmacological effects by acting on two major neurotransmitter systems in the brain:
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High-affinity antagonism
It shows strong binding to the 5-HT₂ receptor (Ki = 0.37 nM) and the dopamine D₄ receptor (Ki = 2.93 nM), effectively blocking receptor activation. -
Receptor selectivity
It has lower affinity for the 5-HT₁A receptor and very low affinity for the 5-HT₃ receptor. It also shows only low to moderate affinity for α₁-adrenergic receptors, dopamine D₂ receptors, and histamine H₁ receptors, giving it a relatively selective pharmacological profile.
Many commonly used antidepressants, especially SSRIs, also contain a piperazine or related moiety, which facilitates binding to biological targets.
Other CNS drugs that may contain similar structural features include antihistamines (anti-allergy and sedative agents) and antitussives.
Applications in Anticancer Drug Research
Derivatives of 1-(4-fluorophenyl)piperazine have also demonstrated strong potential in anticancer drug discovery.
For example, a research group at Peking University used this scaffold to design and synthesize 1-[bis(4-fluorophenyl)methyl]-4-substituted piperazines, some of which showed strong inhibitory activity against human ovarian cancer cell lines.
Another study from Southwest Minzu University introduced the 1-[bis(4-fluorophenyl)methyl]piperazine motif into 1,2,3-triazole derivatives, and the resulting compounds exhibited good inhibitory activity against leukemia, lung cancer, and liver cancer cell lines.
Applications in Agrochemicals
In the agrochemical field, 1-(4-fluorophenyl)piperazine is also an important intermediate for the development of high-efficiency, low-toxicity, and environmentally friendly pesticides.
Insecticides and Acaricides
Using 1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)piperazine as a key intermediate, a series of fluorinated pyridine-piperazine compounds can be synthesized. Bioassay results have shown that some of these compounds exhibit excellent insecticidal and acaricidal activity against pests such as diamondback moths and Spodoptera species.
Fungicides and Herbicides
By combining triazole rings, trifluoromethyl groups, and piperazine rings through Mannich reactions, new compounds have been obtained that show in vitro antifungal activity against a variety of plant pathogens, with some members also exhibiting herbicidal activity.
Product Information
We currently manufacture and supply:
1-(4-Fluorophenyl)piperazine
CAS No.: 2252-63-2
This product is used as an intermediate in the synthesis of the antipsychotic drug Fananserin and is widely applied in antidepressant and anticancer drug research. Its unique molecular structure also makes it highly valuable in the agrochemical sector, especially for the development of environmentally friendly pesticides.
Contact us for more information: info@coreychem.com
