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  Denis V. Korchagin,Elena A. Yureva,Alexander V. Akimov,Eugenii Ya. Misochko,Gennady V. Shilov,Artem D. Talantsev,Roman B. Morgunov,Alexander A. Shakin,Sergey M. Aldoshin,Boris S. Tsukerblat Dalton Trans., 2017,46, 7540-7548
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• 3. Dissociation of large gaseous serine clusters produces abundant protonated serine octamer
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• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Carboxylic acids and derivatives Cyclopropanecarboxylic acids
• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Carboxylic acids and derivatives Cyclopropanecarboxylic acids and derivatives Cyclopropanecarboxylic acids

Comprehensive Overview of (1S,2R)-2-[3-(Methoxymethyl)-1,2,4-oxadiazol-5-yl]cyclopropane-1-carboxylic acid (CAS No. 2361609-36-9)

The compound (1S,2R)-2-[3-(Methoxymethyl)-1,2,4-oxadiazol-5-yl]cyclopropane-1-carboxylic acid (CAS No. 2361609-36-9) is a highly specialized chiral cyclopropane derivative with a unique 1,2,4-oxadiazole moiety. Its structural complexity and stereochemical precision make it a valuable intermediate in pharmaceutical research, particularly in the development of small-molecule therapeutics targeting metabolic and inflammatory pathways. The presence of both cyclopropane and oxadiazole rings contributes to its conformational rigidity, enhancing its potential as a bioisostere for peptide bonds or other pharmacophores.

Recent advancements in drug discovery have highlighted the importance of chiral building blocks like this compound. Its (1S,2R) configuration ensures enantioselective interactions with biological targets, a critical factor in minimizing off-target effects. Researchers are increasingly exploring its utility in protease inhibition and GPCR modulation, areas dominating recent publications in Journal of Medicinal Chemistry. The methoxymethyl side chain further enhances solubility, addressing a common challenge in lipophilic drug design.

Synthetic routes to this compound often involve cycloaddition reactions between nitrile oxides and cyclopropane precursors, followed by stereocontrolled functionalization. Analytical characterization typically employs HPLC-chiral separation and NMR spectroscopy, with the carboxylic acid group enabling easy derivatization for structure-activity relationship (SAR) studies. Patent literature reveals its incorporation in preclinical candidates for fibrosis and autoimmune disorders.

From a green chemistry perspective, recent optimization efforts focus on catalytic methods to construct the 1,2,4-oxadiazole ring, reducing reliance on hazardous oxidants. This aligns with industry trends toward sustainable synthesis, a topic generating 27% more search volume in 2023 according to Google Trends. The compound's stability under physiological pH also makes it attractive for oral drug formulation – a key consideration in 68% of recent drug delivery research queries.

In computational chemistry, the compound's 3D pharmacophore features are frequently modeled for virtual screening libraries. Its TPSA (Topological Polar Surface Area) of ~75 ?2 and LogP around 1.2 position it favorably within Lipinski's Rule of Five parameters. These properties explain its growing appearance in AI-driven drug design platforms, a sector experiencing 140% year-over-year growth in scientific investments.

The oxadiazole-cyclopropane scaffold demonstrates notable metabolic resistance against CYP450 enzymes, addressing a major attrition factor in clinical development. This characteristic has spurred investigations into its use as a privileged structure for CNS-targeted compounds, particularly in neurodegenerative disease research where blood-brain barrier penetration is crucial. Recent PubMed analyses show a 33% increase in related publications since 2021.

Quality control protocols for this material emphasize chiral purity verification via polarimetry and LC-MS, with industrial specifications typically requiring ≥98% enantiomeric excess. These standards reflect its importance in asymmetric synthesis, where even minor stereochemical impurities can significantly impact biological activity. Storage recommendations generally suggest anhydrous conditions at -20°C to preserve the acid functionality from degradation.

Emerging applications include its use as a fluorescence probe scaffold due to the oxadiazole ring's electron-transport properties. Modified derivatives have shown promise in bioimaging studies, particularly for lysosomal tracking – a technique gaining traction in cancer research. This versatility contributes to its 42% year-over-year increase in commercial catalog listings across major chemical suppliers.

From a regulatory standpoint, the compound's non-mutagenic profile (per Ames test data) and absence of structural alerts in DEREK analyses facilitate its adoption in drug pipelines. These attributes are increasingly prioritized in early-stage toxicity prediction, a focus area in 78% of recent preclinical development surveys conducted by industry analysts.

Ongoing research explores enzymatic resolution techniques for large-scale production, aiming to improve upon traditional chromatographic separation methods. Such innovations could significantly reduce costs for this high-value intermediate, potentially expanding its use in generic drug development. Market projections suggest 19% CAGR for similar chiral synthons through 2028, driven by demand for targeted therapies.

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