4-[[(3-Chloro-4-methoxyphenyl)methyl]amino]-2-[(2S)-2-(hydroxymethyl)-1-pyrrolidinyl]-5-pyrimidinecarboxylic acid
[CAS# 330785-84-7]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Pyrimidine
• Name: 4-[[(3-Chloro-4-methoxyphenyl)methyl]amino]-2-[(2S)-2-(hydroxymethyl)-1-pyrrolidinyl]-5-pyrimidinecarboxylic acid
• Molecular Formula: C₁₈H₂₁ClN₄O₄
• Molecular Weight: 392.84
• CAS Registry Number: 330785-84-7
• EC Number: 807-887-0
• SMILES: COC1=C(C=C(C=C1)CNC2=NC(=NC=C2C(=O)O)N3CCC[C@H]3CO)Cl

Properties

• Solubility: Practically insoluble (0.019 g/L) (25 °C), Calc.^*
• Density: 1.415±0.06 g/cm³ (20 °C 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2013 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302
• Safety Statements: P264-P270-P301+P317-P330-P501

Discovery and Applications

4-[[(3-Chloro-4-methoxyphenyl)methyl]amino]-2-[(2S)-2-(hydroxymethyl)-1-pyrrolidinyl]-5-pyrimidinecarboxylic acid is a chemically intricate compound with notable applications in medicinal chemistry. Characterized by its complex structure, this molecule integrates a pyrimidine ring with multiple substituents, including a chloro-methoxyphenyl group, a hydroxymethyl-pyrrolidinyl group, and a carboxylic acid moiety. Its molecular formula is C19H20ClN3O4.

The discovery of this compound is a result of extensive research aimed at developing new pharmaceuticals with enhanced biological activity and specificity. The pyrimidine ring system, as a core structure, is frequently employed in the design of various therapeutic agents due to its ability to interact with numerous biological targets. The introduction of different functional groups can tailor the compound’s pharmacological properties and improve its efficacy and selectivity.

One of the primary applications of 4-[[(3-Chloro-4-methoxyphenyl)methyl]amino]-2-[(2S)-2-(hydroxymethyl)-1-pyrrolidinyl]-5-pyrimidinecarboxylic acid lies in its potential as a therapeutic agent. The chloro and methoxy substituents on the phenyl group can influence the compound’s interaction with specific enzymes or receptors, which may lead to the development of drugs targeting particular biological pathways.

The pyrrolidinyl group in the compound is particularly noteworthy. Pyrrolidine derivatives are known for their ability to interact with biological systems in a variety of ways, making them valuable in the design of new drugs. The hydroxymethyl substitution enhances the compound’s potential for specific binding interactions and may contribute to improved pharmacokinetics and pharmacodynamics.

In the realm of drug development, 4-[[(3-Chloro-4-methoxyphenyl)methyl]amino]-2-[(2S)-2-(hydroxymethyl)-1-pyrrolidinyl]-5-pyrimidinecarboxylic acid may offer significant advantages. Its structural diversity and ability to interact with various biological targets suggest potential applications in treating a range of conditions, including cancer, infectious diseases, and inflammatory disorders.

The carboxylic acid group in the molecule also plays a crucial role in its biological activity. This functional group can influence the compound’s solubility, stability, and binding affinity, contributing to its overall efficacy as a therapeutic agent. Furthermore, the integration of multiple functional groups allows for fine-tuning of the molecule’s properties, which is essential in drug design and development.

The compound’s potential extends beyond therapeutic applications. Its unique combination of substituents may also enable the design of diagnostic tools or imaging agents. By modifying the pyrimidine core and exploring its interactions with various biological systems, researchers can develop new technologies for medical imaging and disease detection.

In conclusion, 4-[[(3-Chloro-4-methoxyphenyl)methyl]amino]-2-[(2S)-2-(hydroxymethyl)-1-pyrrolidinyl]-5-pyrimidinecarboxylic acid represents a significant advancement in medicinal chemistry. Its complex structure and diverse functional groups make it a promising candidate for further research and development in both therapeutic and diagnostic applications.

References

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