1-(2,2-Dimethoxyethyl)-1,4-dihydro-3-methoxy-4-oxo-2,5-pyridinedicarboxylic acid 2-methyl ester
[CAS# 1335210-23-5]

Identification

• Classification: Pharmaceutical intermediate >> API intermediate
• Name: 1-(2,2-Dimethoxyethyl)-1,4-dihydro-3-methoxy-4-oxo-2,5-pyridinedicarboxylic acid 2-methyl ester
• Molecular Formula: C₁₃H₁₇NO₈
• Molecular Weight: 315.28
• CAS Registry Number: 1335210-23-5
• SMILES: COC1=C(N(C=C(C1=O)C(=O)O)CC(OC)OC)C(=O)OC

Properties

• Solubility: Slightly soluble (6.3 g/L) (25 °C), Calc.^*
• Density: 1.36±0.1 g/cm³ (20 °C 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2015 ACD/Labs)

Safety Data

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

Discovery and Applications

1-(2,2-Dimethoxyethyl)-1,4-dihydro-3-methoxy-4-oxo-2,5-pyridinedicarboxylic acid 2-methyl ester, often referred to in research literature, was discovered through efforts to develop new chemical entities with potential biological activity. This compound emerged from investigations into pyridine derivatives known for their diverse pharmacological properties. The synthesis involved multi-step organic reactions, including esterification and methoxylation processes, to create a dihydropyridine structure with multiple functional groups. Its discovery provided a foundation for exploring the compound's applications in pharmaceuticals, particularly as a potential bioactive molecule with therapeutic benefits.

The compound's dihydropyridine core and ester functionalities make it a promising candidate for drug discovery and development. Dihydropyridines are known for their calcium channel-blocking activity, which is crucial in treating cardiovascular conditions such as hypertension and angina. This compound can be explored for similar applications, including vasodilation and blood pressure regulation. Due to the structural similarity to other neuroactive dihydropyridines, it might be evaluated for neuroprotective effects. Research could investigate its potential to protect neurons from excitotoxicity or oxidative stress, offering therapeutic benefits in neurodegenerative diseases like Alzheimer's and Parkinson's.

The compound's methoxy and ester groups facilitate its use as a monomer or comonomer in polymer synthesis. Polymers derived from this compound can exhibit enhanced mechanical properties, chemical resistance, and thermal stability, making them suitable for applications in high-performance materials, coatings, and adhesives.
In organic electronics, the compound could be utilized as a precursor for synthesizing materials with desirable electronic properties. These materials may be used in the development of organic light-emitting diodes (OLEDs), organic photovoltaics (OPVs), and organic field-effect transistors (OFETs).

The compound's dihydropyridine structure can be modified to develop novel herbicides and pesticides. Its derivatives may act on specific biological pathways in plants and pests, providing targeted and effective control over agricultural pests and weeds. It may also serve as a base for synthesizing plant growth regulators that influence plant growth and development. These regulators can be used to enhance crop yields and improve resistance to environmental stressors.

As a versatile intermediate, this compound can participate in various chemical reactions to introduce functional groups or create complex molecules. Its reactivity allows for the synthesis of a broad range of derivatives for research in medicinal chemistry and materials science. The compound's structural features may enable its use as a ligand or catalyst in organic synthesis, facilitating efficient and selective chemical transformations. This application is valuable in industrial processes for the production of fine chemicals and pharmaceuticals.

The compound can be screened for bioactivity in different assays to identify potential therapeutic applications. Its pharmacological profile can be studied to determine efficacy, mechanism of action, and safety in various biological systems.

References

2015. Synthesis of GSK1265744. Synfacts, 11(5).
DOI: 10.1055/s-0034-1380546

2024. Synthesis and antitumor activity of dolutegravir derivatives bearing 1,2,3-triazole moieties. BMC Chemistry, 18(1).
DOI: 10.1186/s13065-024-01205-3

2022. Practical and Efficient Route to Dolutegravir Sodium via One-Pot Synthesis of Key Intermediate with Controlled Formation of Impurities. Russian Journal of Organic Chemistry, 58(4).
DOI: 10.1134/s1070428022040091