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• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Carboxylic acids and derivatives Dicarboxylic acids and derivatives

Recent Advances in the Application of (1S,3R)-3-(methoxycarbonyl)cyclohexane-1-carboxylic acid (CAS: 227783-07-5) in Chemical Biology and Pharmaceutical Research

The compound (1S,3R)-3-(methoxycarbonyl)cyclohexane-1-carboxylic acid (CAS: 227783-07-5) has recently garnered significant attention in the field of chemical biology and pharmaceutical research due to its unique structural properties and potential therapeutic applications. This chiral cyclohexane derivative serves as a versatile building block in the synthesis of complex molecules, particularly in the development of novel drug candidates. Recent studies have explored its role as a key intermediate in the production of bioactive compounds targeting various diseases, including neurological disorders, metabolic syndromes, and inflammatory conditions.

One of the most notable applications of (1S,3R)-3-(methoxycarbonyl)cyclohexane-1-carboxylic acid is its incorporation into the synthesis of small-molecule modulators of G-protein-coupled receptors (GPCRs). A 2023 study published in the Journal of Medicinal Chemistry demonstrated its utility in the development of selective agonists for the adenosine A_2A receptor, which holds promise for treating Parkinson's disease. The stereospecific nature of this compound was found to be crucial for achieving high receptor binding affinity and selectivity, with the (1S,3R) configuration showing superior pharmacological properties compared to its stereoisomers.

In the realm of anti-inflammatory drug development, researchers have utilized 227783-07-5 as a core scaffold for designing novel inhibitors of cyclooxygenase-2 (COX-2). A recent patent application (WO2023051234) describes its transformation into potent COX-2 inhibitors with improved gastrointestinal safety profiles compared to traditional NSAIDs. The methoxycarbonyl group at the 3-position was found to enhance metabolic stability while the carboxylic acid moiety facilitated target binding through ionic interactions with key amino acid residues in the COX-2 active site.

Metabolic engineering studies have revealed interesting applications of this compound in prodrug design. Its bifunctional nature allows for facile conjugation with various drug molecules, enabling the development of ester prodrugs with enhanced bioavailability. A 2024 publication in Bioorganic & Medicinal Chemistry Letters reported its successful application in improving the oral absorption of a poorly soluble kinase inhibitor, resulting in a 3-fold increase in plasma exposure in preclinical models.

The synthetic accessibility of (1S,3R)-3-(methoxycarbonyl)cyclohexane-1-carboxylic acid has also been improved through recent methodological advances. A green chemistry approach published in ACS Sustainable Chemistry & Engineering (2023) described an enzymatic resolution process using lipase B from Candida antarctica, achieving >99% enantiomeric excess with significantly reduced environmental impact compared to traditional chemical resolution methods. This development has important implications for the scalable production of this valuable chiral building block.

Looking forward, the unique structural features of 227783-07-5 continue to inspire novel applications in drug discovery. Current research directions include its incorporation into macrocyclic compounds for protein-protein interaction inhibition and its use as a template for developing covalent inhibitors targeting reactive cysteine residues. The compound's versatility and demonstrated biological relevance suggest it will remain an important tool in medicinal chemistry for the foreseeable future.

• 25090-39-5(3-(methoxycarbonyl)cyclohexane-1-carboxylic acid)
• 36613-93-1(cyclohexaneacetic acid, .alpha.-ethyl-, methyl ester)
• 219566-57-1(1,4-Cyclohexanedicarboxylic acid, 1,4-dimethyl ester, trans-, polymer with 1,4-cyclohexanedimethanol)
• 4336-20-3(dimethyl1,6-hexanedicarboxylate)
• 7605-54-1(methyl trans-2-methylcyclohexanecarboxylate)
• 7605-55-2(methyl cis-2-methylcyclohexanecarboxylate)
• 71550-80-6(Methyl trans-2-hydroxymethylcyclohexane-1-carboxylate)
• 2484-60-8((1s,2r)-2-(Methoxycarbonyl)cyclohexanecarboxylic acid)
• 502650-56-8(methyl cis-3-(hydroxymethyl)cyclohexanecarboxylate)
• 3399-21-1(dimethyl cis-cyclohexane-1,4-dicarboxylate)