27469-60-9 | 4,4'-Difluorobenzhydrylpiperazine

CAS:27469-60-9 | 4,4'-Difluorobenzhydrylpiperazine,Description

1-[Bis(4-fluorophenyl)methyl]piperazine is a chemical compound that has been studied for various applications, including its potential as an antimicrobial agent and its role in the synthesis of pharmaceuticals. The compound features a piperazine core substituted with a bis(4-fluorophenyl)methyl group, which is a structural motif found in several bioactive molecules.

Synthesis Analysis

The synthesis of 1-[Bis(4-fluorophenyl)methyl]piperazine derivatives has been explored in several studies. For instance, novel N-alkyl and N-sulfonyl derivatives of this compound were synthesized and characterized by IR and 1H NMR spectroscopy. Another study reported the synthesis of related compounds to investigate their potential as antioxidants through the Mannich reaction. Additionally, the synthesis of metabolites related to 1-[Bis(4-fluorophenyl)methyl]piperazine dihydrochloride, a cerebral vasodilator, was performed to confirm their structures.

Molecular Structure Analysis

The molecular structure of 1-[Bis(4-fluorophenyl)methyl]piperazine and its derivatives has been determined using various techniques. X-ray analysis revealed the crystal and molecular structure of a related compound, showing the piperazine ring adopting a chair conformation and the benzimidazole ring forming a dihedral angle with the fluorophenyl ring. The crystal structure of 1-[Bis(4-fluorophenyl)methyl]piperazine-1,4-diium dimaleate was also determined, highlighting very short intramolecular hydrogen bonds within the maleate anions.

Chemical Reactions Analysis

The chemical reactivity of 1-[Bis(4-fluorophenyl)methyl]piperazine has been utilized in the synthesis of various pharmaceuticals. For example, it served as a key intermediate in the synthesis of Fluspirilen and Penfluridol, neuroleptic agents, through a rhodium-catalyzed hydroformylation reaction. The compound's derivatives have also been tested for their 5-HT2 antagonist activity, indicating their potential use in treating conditions related to serotonin receptors.

Physical and Chemical Properties Analysis

The physical and chemical properties of 1-[Bis(4-fluorophenyl)methyl]piperazine derivatives have been evaluated in several studies. For instance, the antimicrobial activity of synthesized derivatives was assessed against various Gram-positive and Gram-negative bacteria, with some compounds showing potent activities. The antioxidant activity of a synthesized derivative was tested, revealing potential as an antioxidant. Additionally, the binding affinity of chiral derivatives for the dopamine transporter was investigated, identifying compounds with high affinity and selectivity, which could be beneficial in treating cocaine abuse.

Scientific Research Applications

Synthesis Applications

• Synthesis of Flunarizine and Its Isomers : 1-[Bis(4-fluorophenyl)methyl]piperazine is used in the industrial production of Flunarizine, a calcium channel blocker with vasodilating and antihistamine activities, through condensation reactions (Shakhmaev, Sunagatullina, & Zorin, 2016).
• Antimigraine Drug Synthesis : It serves as a starting material in the synthesis of Lomerizine, an antimigraine drug, indicating its importance in pharmaceutical manufacturing (Narsaiah & Kumar, 2010).
• Synthesis of Medicinally Important Derivatives : Novel substituted derivatives of 1-[bis(4-fluorophenyl)-methyl]piperazine have been synthesized and evaluated as antimicrobial agents, showcasing its versatility in medicinal chemistry (Narendra Sharath Chandra et al., 2006).

Biochemical and Pharmacological Studies

• Studies on Metabolites : Research into the metabolites of compounds like KB-2796, a cerebral vasodilator, which is a derivative of 1-[bis(4-fluorophenyl)methyl]piperazine, contributes to understanding drug metabolism and biotransformation (Ohtaka, Hori, Iemura, & Yumioka, 1989).
• Exploring Binding Characteristics : The binding of derivatives of 1,4-bis((4-((4-heptylpiperazin-1-yl)methyl)-1H-1, 2, 3-triazol-1-yl)methyl)benzene, a piperazine derivative, to bovine serum albumin was investigated, which is crucial for understanding pharmacokinetic mechanisms (Karthikeyan et al., 2015).
• Antibacterial and Biofilm Inhibition Studies : Piperazine derivatives, including 1,4-bis[(1-hydroxy-4-t-butyl-phenyl)methyl]piperazine, have been studied for their antibacterial efficacies and biofilm inhibition activities, highlighting their potential in microbial resistance research (Mekky & Sanad, 2020).

Chemical Properties and Reactions

• Study of Chemical Reactions : Investigations into the Leuckart-Wallach reaction involving 1-[Bis-(4-fluorophenyl)methyl]piperazine provide insights into its chemical reactivity and potential applications in synthetic chemistry (Zhou Ping, 2002).

Safety And Hazards

This chemical is considered hazardous by the 2012 OSHA Hazard Communication Standard (29 CFR 1910.1200). It is toxic if swallowed, causes skin irritation, causes serious eye irritation, and may cause respiratory irritation. It is advised to avoid breathing dust/fume/gas/mist/vapors/spray and to use only outdoors or in a well-ventilated area.

Future Directions

While specific future directions for 1-[Bis(4-fluorophenyl)methyl]piperazine are not mentioned in the search results, its use in the synthesis of various compounds suggests potential applications in the development of new pharmaceuticals.

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