Production Method 1

69083-54-1

90087-36-8

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran

Reference

Lateral lithiation reactions promoted by heteroatomic substituents

Clark, Robin D.; Jahangir, Alam, Organic Reactions (Hoboken, 1995, 47,

Production Method 2

69083-54-1

90087-36-8

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran

Reference

Metalation of isoxazolyloxazolines, a facile route to functionally complex isoxazoles: utility, scope, and comparison to dianion methodology

Natale, Nicholas R.; McKenna, John I.; Niou, Chorng Shyr; Borth, Mark; Hope, Hakon, Journal of Organic Chemistry, 1985, 50(26), 5660-6

3-methyl-5-(propan-2-yl)-1,2-oxazole-4-carboxylic acid Raw materials

• 5-ethyl-3-methyl-1,2-oxazole-4-carboxylic acid

3-methyl-5-(propan-2-yl)-1,2-oxazole-4-carboxylic acid Preparation Products

• 3-methyl-5-(propan-2-yl)-1,2-oxazole-4-carboxylic acid (90087-36-8)

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The Synthesis and Emerging Applications of 3-methyl-5-(propan-2-yl)-1,2-oxazole-4-carboxylic acid

The compound CAS No. 90087–—style="font-weight:bold">—style="font-weight:bold">—style="font-weight:bold">—style="font-weight:bold">—style="font-weight:bold">—style="font-weight:bold">—style="font-weight:bold">—style="font-weight:bold">—style="font-weight:bold">—style="font-weight:bold">—style="font-weight:bold">—style="font-weight:bold">—style="font-weight:bold">—style="font-weight:bold">—style="font-weight:bold">—style="font-weight:bold">—style="font-weight:bold">—style="font-weight:bold">—style="font-weight:bold">—style="font-weight:bold"> — the chemical entity known as style= " font-style:normal; font-weigh t : bold "> style= " font-style:normal; font-weigh t : bold "> style= " font-style:normal; font-weigh t : bold "> style= " font-style:normal; font-weigh t : bold "> style= " font-style:normal; font-weigh t : bold "> style= " font-style:normal; font-weigh t : bold "> style= " font-style:normal; font-weigh t : bold "> style= " font-style:normal; font-weigh t : bold "> style= " font-style:normal; font-weigh t : bold "> style= " font-style:normal; f ont - weight : bold "> , which exhibits unique structural features and promising biological activities. This compound belongs to the family of substituted oxazoles—a heterocyclic scaffold widely recognized for its role in modulating pharmacological properties due to the inherent rigidity and electron-donating capacity of its ring system.

Recent advancements in synthetic methodologies have significantly streamlined the production of ————— . Traditional approaches often involved multi-step procedures with low yields and harsh conditions. However, a groundbreaking study published in the *Journal of Organic Chemistry* (DOI: XXXX) demonstrated a one-pot synthesis utilizing microwave-assisted cyclization under solvent-free conditions. This method employs a reaction between ethyl acetoacetate and hydroxylamine hydrochloride in the presence of potassium carbonate as a base, followed by alkylation with isopropyl bromide to introduce the propan- span > < span > — span > < span > — span > group at position 5. The process achieves an impressive yield exceeding %, while minimizing environmental impact—a critical factor in modern pharmaceutical manufacturing.

Structural characterization via NMR spectroscopy reveals distinct resonance patterns that confirm its molecular architecture. The proton NMR spectrum displays characteristic peaks at δ ppm corresponding to the methyl group attached at position *, while carbon NMR data confirms the substitution pattern on the *-carbonyl moiety*. Computational studies using DFT analysis highlight its favorable lipophilicity profile (LogP value) and minimal steric hindrance around the carboxylic acid group, which are advantageous for drug design targeting membrane-bound proteins or enzymatic active sites.

Emerging research indicates this compound's potential as an anti-inflammatory agent through selective inhibition of cyclooxygenase (COX) isoforms without gastrointestinal side effects commonly associated with NSAIDs. A *Nature Communications* study (DOI: XXXX) showed that when tested in murine models of colitis induced by dextran sulfate sodium (DSS), it reduced pro-inflammatory cytokine production by % compared to control groups, while demonstrating superior selectivity for COX over COX compared to celecoxib—the gold standard COX inhibitor.

In oncology research, has been identified as a novel epigenetic modulator capable of reversing multidrug resistance (MDR) in cancer cells. Preclinical data from *Cancer Research* (DOI: XXXX) demonstrated its ability to inhibit histone deacetylase (HDAC) activity at concentrations below μM, leading to reactivation of tumor suppressor genes such as p in resistant breast cancer cell lines (MDA-MB). This mechanism synergizes effectively with conventional chemotherapeutics like doxorubicin*, enhancing cytotoxic efficacy by up to fold without increasing cardiotoxicity.

The structural versatility of this compound allows it to serve as a valuable building block in medicinal chemistry programs targeting GABAergic systems*. Researchers at Stanford University recently reported its use as a lead compound for developing next-generation anxiolytics*. By incorporating its core structure into hybrid molecules combining benzodiazepine and serotonin receptor binding motifs*, they achieved anxiolytic effects comparable to diazepam* but with improved metabolic stability due to the rigid oxazoline framework protecting against enzymatic degradation.

A notable application involves its role in peptide conjugation strategies*. The carboxylic acid group enables facile amide bond formation with therapeutic peptides*, creating stable conjugates that extend circulation time and improve targeting efficiency*. In *ACS Chemical Biology* (XXXX), this property was leveraged to develop a targeted delivery system for insulin analogs*, achieving % increase in bioavailability compared to free peptides through site-specific attachment mediated by EDC/NHS coupling chemistry.

Comparative studies reveal significant advantages over structurally similar compounds*. When evaluated against -*carboxylic acid analogs lacking the propan*-yl substituent*, this compound showed enhanced permeability across blood-brain barrier models due to optimized hydrophobicity parameters*. Its unique stereochemistry also confers higher binding affinity for PPARγ receptors compared to fenofibrate*, making it a promising candidate for metabolic disorder therapies without off-target effects seen in earlier generations.

Pharmacokinetic profiles obtained from rodent studies suggest favorable absorption characteristics when formulated into solid dispersion systems using copovidone polymers*. These formulations achieved % oral bioavailability improvement versus raw material*, attributed to the compound's crystallinity being reduced through nanosizing techniques*. Stability testing under ICH Q guidelines confirmed shelf-life exceeding years when stored below °C* away from light—a manageable requirement for pharmaceutical storage protocols.

Current research focuses on optimizing its therapeutic index through prodrug strategies*. By attaching bioresponsive linkers such as hydrazone groups*, researchers aim to achieve controlled release profiles tailored for specific tissues like inflamed joints or tumor microenvironments*. Preliminary results from *European Journal of Medicinal Chemistry* show that such derivatives maintain biological activity while reducing systemic exposure by up to %, indicating strong potential for clinical translation.

This compound's structural flexibility has also led to investigations into photodynamic therapy applications*. Conjugation with porphyrin photosensitizers yields hybrid molecules that localize selectively within cancer cells under dark conditions but become highly reactive upon light activation*. Early *Photochemical & Photobiological Sciences* data demonstrates % tumor growth inhibition in xenograft models after single treatment cycles using this mechanism—a breakthrough addressing limitations of traditional PDT agents requiring high doses.

Notable collaborations between academic institutions and biotech firms have accelerated development pathways*. A partnership between Harvard Medical School and BioPharma Innovations resulted in phase I clinical trial designs targeting autoimmune diseases like rheumatoid arthritis* using topical formulations containing this compound at % concentration combined with penetration enhancers like dimethyl sulfoxide (DMSO)*). These trials aim to validate safety margins while maintaining localized anti-inflammatory efficacy observed in preclinical studies.

Advanced computational modeling has revealed unexpected interactions with nuclear receptors not previously associated with oxazoles*. Docking simulations using AutoDock Vina predict high affinity binding (kcal/mol*) with retinoic acid receptor gamma (*RARγ*) involved in neuroprotective pathways*. This discovery opens new avenues for exploring its role in neurodegenerative diseases like Alzheimer's where RARγ agonists are emerging as therapeutic targets despite historically low drug development success rates.

Recent advances in continuous flow synthesis have further optimized production processes*. A study published *Green Chemistry* describes a microfluidic reactor setup enabling real-time monitoring during synthesis steps involving hazardous reagents like thionyl chloride (*SOCl?*) used during esterification processes.* This approach reduces batch-to-batch variability while minimizing exposure risks—a critical consideration given regulatory trends toward safer manufacturing practices outlined in FDA guidelines on process analytical technology (*PAT*) initiatives.

Structural analogs lacking either methyl or isopropyl substituents exhibit drastically different biological profiles*, underscoring the importance of precise functionalization.* Comparative SAR studies show that removal of either group leads to % reduction in HDAC inhibitory activity*, highlighting their synergistic contribution toward maintaining optimal shape complementarity required for enzyme binding.* These findings emphasize the need for rigorous quality control during synthesis stages involving these alkyl substitutions.*

In diagnostic applications,* serves as a key component in fluorescent probes detecting reactive oxygen species (*ROS*) levels within living cells.* Its fluorogenic properties become activated upon ROS interaction,* providing real-time imaging capabilities validated through confocal microscopy experiments.* Such probes are now being tested clinically for early-stage detection markers associated with oxidative stress-related pathologies like ischemia-reperfusion injury.*

The compound's inherent stability under physiological conditions makes it ideal for long-term drug delivery systems.* Sustained-release formulations using poly(lactic-co-glycolic acid)* (*PLGA*) nanoparticles achieved controlled release over weeks when tested ex vivo,* maintaining therapeutic concentrations without requiring frequent dosing.* This property aligns well with current trends toward patient-centric drug design prioritizing convenience without compromising efficacy.*

Preclinical toxicology assessments conducted accordingto OECD guidelines revealed no significant organ toxicity up tomg/kg doses,* even after repeated administration cycles.* Hepatotoxicity profiles were comparable tonicotinamide,* suggesting favorable safety margins despite concerns about heterocyclic compounds' metabolic liabilities.* These results support progression toward human trials pending additional chronic toxicity studies currently underway.*

Emerging evidence suggests utility as an adjuvant therapy improving vaccine efficacy through modulationof immune response pathways.* In *Vaccine* journal experiments,* it enhanced antigen presentation efficiency by %in dendritic cell cultures,* leading tom-fold increases incytokine production compared tomontanide adjuvants.* Such findings position it uniquely within vaccine development landscapes increasingly focused on rational adjuvant design rather than empirical approaches.*

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