Hydroxyacetic acid - (1S)-1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline (1:1)
[CAS# 97232-75-2]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Quinoline compound
• Name: Hydroxyacetic acid - (1S)-1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline (1:1)
• Synonyms: Einecs 306-417-7; 2-hydroxyacetic acid (1S)-1-[(4-methoxyphenyl)methyl]-1,2,3,4,5,6,7,8-octahydroisoquinoline
• Molecular Formula: C₁₉H₂₇NO₄
• Molecular Weight: 333.42
• CAS Registry Number: 97232-75-2
• EC Number: 306-417-7
• SMILES: COC1=CC=C(C=C1)C[C@H]2C3=C(CCCC3)CCN2.C(C(=O)O)O

Discovory and Applicatios

Hydroxyacetic acid - (1S)-1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline (1:1) represents a significant compound in the realm of organic chemistry, particularly in the development of novel pharmaceuticals and advanced materials. This compound is an equimolar salt formed between hydroxyacetic acid and (1S)-1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline, and it has gained attention for its unique properties and potential applications.

The discovery of this compound is rooted in the study of isoquinoline derivatives, which are known for their wide range of biological activities. The combination of hydroxyacetic acid with the chiral isoquinoline derivative creates a salt that possesses both acidity and basicity, allowing for versatile interactions in biological and chemical systems. The stereochemistry of the (1S)-isoquinoline moiety is particularly important, as it influences the compound's interactions with enzymes and receptors in biological systems.

In terms of synthesis, Hydroxyacetic acid - (1S)-1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline (1:1) can be prepared through a straightforward acid-base reaction between the two components. The choice of hydroxyacetic acid as a counterion is strategic, as it introduces hydrophilic properties to the otherwise hydrophobic isoquinoline derivative. This enhances the solubility of the compound in aqueous environments, making it more suitable for biological applications.

The primary application of this compound lies in its potential use as a pharmaceutical intermediate. The octahydroisoquinoline structure is a core scaffold in many bioactive molecules, and its incorporation into drug candidates can lead to compounds with enhanced efficacy and selectivity. The presence of the (1S)-chiral center allows for specific interactions with chiral biological targets, which is crucial in the design of drugs with minimal side effects and optimized therapeutic profiles.

Furthermore, Hydroxyacetic acid - (1S)-1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline (1:1) has shown promise in preliminary studies as a potential lead compound for the development of treatments for neurological disorders. The compound’s ability to cross the blood-brain barrier, coupled with its interaction with neurotransmitter receptors, suggests its potential use in addressing conditions such as depression, anxiety, and neurodegenerative diseases. Additionally, the compound's structure allows for further chemical modification, providing a platform for the development of a wide range of analogs with varying biological activities.

The discovery and application of Hydroxyacetic acid - (1S)-1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline (1:1) underscore the importance of combining small organic molecules with therapeutic potential. Its synthesis is relatively simple, yet the resulting compound offers significant versatility in drug design. As research progresses, this compound is likely to serve as a valuable tool in the development of new pharmaceuticals, particularly in the treatment of complex neurological conditions.