2-[(S)-(4-Chlorophenyl)(4-piperidinyloxy)methyl]pyridine (2R,3R)-2,3-Dihydroxybutanedioate
[CAS# 210095-58-2]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound
• Name: 2-[(S)-(4-Chlorophenyl)(4-piperidinyloxy)methyl]pyridine (2R,3R)-2,3-Dihydroxybutanedioate
• Synonyms: (S)-2-((4-Chlorophenyl)(piperidin-4-yloxy)methyl)pyridine (2R,3R)-2,3-dihydroxysuccinate
• Molecular Formula: C₁₇H₁₉ClN₂O^.C₄H₆O₆
• Molecular Weight: 452.89
• CAS Registry Number: 210095-58-2
• EC Number: 696-011-9
• SMILES: C1CNCCC1O[C@@H](C2=CC=C(C=C2)Cl)C3=CC=CC=N3.[C@@H]([C@H](C(=O)O)O)(C(=O)O)O

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Discovory and Applicatios

2-[(S)-(4-Chlorophenyl)(4-piperidinyloxy)methyl]pyridine (2R,3R)-2,3-Dihydroxybutanedioate is a chemical substance with a structure that combines a pyridine ring with a piperidine moiety and a chiral dihydroxybutanedioate group. This compound represents a complex molecule with distinct steric and electronic properties, making it of particular interest in the fields of medicinal chemistry and chemical synthesis. The specific molecular configuration, including the chiral centers, contributes to its unique reactivity and potential applications in pharmaceutical development.

The discovery of this compound was part of ongoing research aimed at developing new therapeutic agents, particularly those targeting the central nervous system (CNS). Pyridine derivatives have long been studied for their bioactivity, with many exhibiting significant pharmacological effects. The incorporation of the piperidinyloxy and chlorophenyl groups introduces additional functional features, which may influence the molecule’s interaction with biological targets. The (2R,3R)-2,3-dihydroxybutanedioate part of the molecule is a key structural element that imparts chiral specificity, potentially affecting the compound's binding affinity and pharmacodynamics.

One of the most promising applications of 2-[(S)-(4-chlorophenyl)(4-piperidinyloxy)methyl]pyridine (2R,3R)-2,3-dihydroxybutanedioate lies in drug discovery and the development of novel therapeutics. The compound’s structure suggests that it could interact with a range of biological targets, including receptors and enzymes that are involved in neurological processes. For example, its piperidine ring, a common motif in CNS-active drugs, could enable it to interact with neurotransmitter systems, such as dopaminergic or serotonergic pathways. This makes the compound a candidate for exploration in the treatment of disorders such as schizophrenia, depression, or Parkinson’s disease.

The chiral centers in the molecule, specifically in the dihydroxybutanedioate segment, add another layer of complexity and specificity to its potential interactions with biological systems. Chiral compounds are often of particular interest in the pharmaceutical industry because they can exhibit differing pharmacological effects based on their enantiomeric configuration. The (2R,3R)-dihydroxybutanedioate configuration is expected to influence the compound's binding and activity, which may result in increased selectivity for certain receptors or enzymes, potentially reducing side effects and improving therapeutic efficacy.

In chemical synthesis, 2-[(S)-(4-chlorophenyl)(4-piperidinyloxy)methyl]pyridine (2R,3R)-2,3-dihydroxybutanedioate may be used as a building block for more complex molecules, particularly in the development of other pharmaceutical candidates. Its ability to serve as a chiral auxiliary or as part of a larger molecular framework could make it useful in the synthesis of novel compounds with enhanced biological activity or specificity. Additionally, the presence of the chlorophenyl and piperidinyloxy groups provides opportunities for further functionalization, allowing chemists to modify the molecule to improve its pharmacological properties.

Another potential application of this compound is in the field of catalysis. The presence of both nitrogen and oxygen-containing functional groups suggests that the compound may exhibit interesting reactivity in synthetic chemistry. For instance, it could be employed in catalytic processes that require specific coordination chemistry, or in the synthesis of other complex organic molecules. This versatility in chemical reactivity opens up further applications in industrial chemistry and material science.

In summary, 2-[(S)-(4-chlorophenyl)(4-piperidinyloxy)methyl]pyridine (2R,3R)-2,3-dihydroxybutanedioate is a multifunctional compound with significant potential in medicinal chemistry and chemical synthesis. Its unique structure, which combines a pyridine ring with functional groups like piperidinyloxy and dihydroxybutanedioate, makes it an attractive candidate for drug development, particularly in CNS-targeted therapies. As research continues, this compound may lead to new treatments for a range of neurological disorders or serve as a valuable tool in the synthesis of more complex molecules.