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1-(4-Chlorophenyl)piperazine derivative

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Identification
Molecular formula
C23H24ClN3O2
CAS number
36286-72-5
IUPAC name
2-[4-(4-chlorophenyl)piperazin-1-yl]ethyl 3-(1H-indol-3-yl)prop-2-enoate
State
State

At room temperature, it exists in a solid state.

Melting point (Celsius)
160.00
Melting point (Kelvin)
433.00
Boiling point (Celsius)
418.00
Boiling point (Kelvin)
691.00
General information
Molecular weight
387.91g/mol
Molar mass
387.8830g/mol
Density
1.3000g/cm3
Appearence

This compound appears as a crystalline solid. The color can vary from white to off-white depending on the purity and preparation method.

Comment on solubility

Solubility of 2-[4-(4-chlorophenyl)piperazin-1-yl]ethyl 3-(1H-indol-3-yl)prop-2-enoate

The solubility of the compound 2-[4-(4-chlorophenyl)piperazin-1-yl]ethyl 3-(1H-indol-3-yl)prop-2-enoate can be influenced by several factors, including its structural characteristics and the nature of the solvent. This compound is likely to exhibit varying solubility in different solvents due to the presence of both hydrophobic and hydrophilic functional groups.

Factors Influencing Solubility:

  • Polarity: The balance between the polar indole moiety and the more hydrophobic chlorophenyl and piperazine groups can affect how well the compound dissolves in polar versus non-polar solvents.
  • Hydrogen Bonding: Potential hydrogen bonding sites within the molecule may enhance solubility in polar solvents, allowing for interaction with water molecules.
  • Temperature: As temperature increases, solubility often improves, especially for organic compounds, which may dissolve more readily when heated.
  • pH Levels: The solubility of this compound could be pH-dependent, particularly if protonation of amine groups occurs in acidic conditions, potentially increasing solubility.

Experiments may reveal that the compound is more soluble in organic solvents such as dimethyl sulfoxide (DMSO) or ethanol, while being poorly soluble in water. This is common among many organic compounds containing bulky aromatic systems. In summary, understanding the solubility of 2-[4-(4-chlorophenyl)piperazin-1-yl]ethyl 3-(1H-indol-3-yl)prop-2-enoate is critical for its application in pharmaceuticals and chemical synthesis.

Interesting facts

Interesting Facts about 2-[4-(4-chlorophenyl)piperazin-1-yl]ethyl 3-(1H-indol-3-yl)prop-2-enoate

This compound is a fascinating example of a synthetic molecule that bridges the fields of medicinal chemistry and pharmacology. It belongs to a class of compounds that incorporate both piperazine and indole moieties, which are known for their intriguing biological activities.

Biological Significance

The presence of the piperazine ring in this compound often leads to enhanced activity as a neuroactive agent. The following points highlight key aspects related to its biological properties:

  • Psychoactive Potential: Compounds with similar structures are frequently researched for their potential as antidepressants or antipsychotics, given the role of serotonin receptors in these conditions.
  • Drug Design: The incorporation of the indole structure is also vital, as indoles are known to interact with various neurotransmitter systems.
  • Pharmacophore: This particular compound may serve as a pharmacophore for developing new medications targeting mental health disorders.

Structure-Activity Relationship (SAR)

In medicinal chemistry, the concept of SAR is crucial. This compound demonstrates how minor modifications in molecular structure can significantly influence its biological activity:

  • Chlorophenyl Substituent: The presence of a 4-chlorophenyl group likely enhances interaction with biological targets, improving selectivity and potency.
  • Piperazine Linkage: The piperazine moiety can enhance water solubility, facilitating better bioavailability in pharmaceutical applications.

Applications and Research

Research into compounds like this one is ongoing, as scientists explore their potential applications, which include:

  • Development of new psychotropic medications
  • Treatments for anxiety and mood disorders
  • Investigating their roles in neuromodulation and cognitive enhancement

In conclusion, 2-[4-(4-chlorophenyl)piperazin-1-yl]ethyl 3-(1H-indol-3-yl)prop-2-enoate showcases the complexities of synthetic organic compounds and their relevance in developing therapeutic agents. Its unique structure and potential applications make it a compelling subject for ongoing scientific study.