5,6-Dihydro-3-(4-morpholinyl)-1-[4-(2-oxo-1-piperidinyl)phenyl]-2(1H)-pyridinone
[CAS# 545445-44-1]

Identification

• Classification: Organic raw materials >> Ketone compound
• Name: 5,6-Dihydro-3-(4-morpholinyl)-1-[4-(2-oxo-1-piperidinyl)phenyl]-2(1H)-pyridinone
• Synonyms: 3-Morpholin-4-yl-1-[4-(2-oxopiperidin-1-yl)phenyl]-5,6-dihydro-1H-pyridin-2-one
• Molecular Formula: C₂₀H₂₅N₃O₃
• Molecular Weight: 355.43
• CAS Registry Number: 545445-44-1
• EC Number: 883-022-0
• SMILES: C1CCN(C(=O)C1)C2=CC=C(C=C2)N3CCC=C(C3=O)N4CCOCC4

Properties

• Density: 1.267

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

5,6-Dihydro-3-(4-morpholinyl)-1-[4-(2-oxo-1-piperidinyl)phenyl]-2(1H)-pyridinone is a compound that belongs to the pyridinone class, which has drawn attention in medicinal chemistry for its therapeutic potential. The structure of this molecule includes a pyridinone ring, a morpholine group, and a phenyl ring attached to a piperidone moiety. This combination of functional groups contributes to its biological activity, particularly in the modulation of various enzyme systems and receptor targets.

The discovery of 5,6-dihydro-3-(4-morpholinyl)-1-[4-(2-oxo-1-piperidinyl)phenyl]-2(1H)-pyridinone can be linked to ongoing research aimed at designing compounds that inhibit phosphodiesterases (PDEs) and other key enzymes involved in cellular signaling. PDE inhibitors are of significant interest in pharmaceutical development due to their role in regulating intracellular levels of cyclic nucleotides, which are crucial for processes such as muscle relaxation, inflammation control, and vasodilation. The inclusion of the morpholine and piperidone groups in this compound’s structure enhances its potential as an inhibitor by providing additional binding interactions with target enzymes.

One of the primary applications of this compound is in the treatment of cardiovascular diseases, where PDE inhibitors like 5,6-dihydro-3-(4-morpholinyl)-1-[4-(2-oxo-1-piperidinyl)phenyl]-2(1H)-pyridinone are used to regulate blood pressure and improve heart function by promoting vasodilation. This effect is achieved through the inhibition of specific PDE enzymes, which leads to an increase in cyclic nucleotide levels, causing smooth muscle relaxation and improved blood flow. Additionally, compounds of this type have shown promise in the treatment of pulmonary hypertension and heart failure.

Another emerging application of this compound is its potential use in neurological disorders. PDE inhibitors are being explored for their role in enhancing memory and cognitive function, as well as in treating conditions such as depression and anxiety. The ability of 5,6-dihydro-3-(4-morpholinyl)-1-[4-(2-oxo-1-piperidinyl)phenyl]-2(1H)-pyridinone to cross the blood-brain barrier and modulate signaling pathways in the central nervous system makes it a candidate for further research in neuropharmacology.

References

2019. Analytical Quality by Design Approach for a Stability-Indicating Method to Determine Apixaban and Its Related Impurities. Chromatographia, 82(11).
DOI: 10.1007/s10337-019-03815-9