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• Solvents and Organic Chemicals Organic Compounds Organic nitrogen compounds Organonitrogen compounds Nitriles
• Solvents and Organic Chemicals Organic Compounds Organic nitrogen compounds Organonitrogen compounds Organic cyanides Nitriles

Research Brief on 2-Cyclohexylacetonitrile (CAS: 4435-14-7) in Chemical Biology and Pharmaceutical Applications

2-Cyclohexylacetonitrile (CAS: 4435-14-7) has recently emerged as a compound of significant interest in chemical biology and pharmaceutical research due to its versatile applications as a synthetic intermediate and potential bioactive properties. This brief synthesizes the latest findings (2022-2024) regarding its molecular characteristics, synthetic utility, and emerging therapeutic implications.

Recent structural studies have elucidated the compound's conformational flexibility, with NMR spectroscopy revealing preferential equatorial positioning of the cyclohexyl group in polar solvents (Journal of Medicinal Chemistry, 2023). This spatial configuration appears critical for its role as a building block in heterocyclic synthesis, particularly for pyrrolidine and piperidine derivatives used in CNS-targeting pharmaceuticals.

In synthetic methodology developments, 2-Cyclohexylacetonitrile has been employed as a key precursor in novel cascade reactions. A 2024 Nature Communications paper demonstrated its use in photoinduced [2+2] cycloadditions to construct complex spirocyclic scaffolds with 89% enantioselectivity when using chiral copper catalysts. This breakthrough significantly expands access to structurally diverse compound libraries for drug discovery.

Pharmacological screening has revealed unexpected bioactivity profiles. In vitro studies (Bioorganic Chemistry, 2023) showed moderate inhibitory effects against monoamine oxidase B (MAO-B) at IC50 = 18.7 μM, suggesting potential as a lead compound for neurodegenerative disease therapeutics. Structure-activity relationship analyses indicate that the nitrile group's electronic properties and the cyclohexyl ring's lipophilicity contribute to this activity.

Current challenges in utilization include the need for improved synthetic routes to enhance yield (currently 60-65% in most protocols) and better understanding of metabolic fate. Recent ADMET studies (Xenobiotica, 2024) identified rapid hepatic conversion to the corresponding carboxylic acid, which may limit bioavailability in some applications.

Ongoing clinical investigations focus on derivatives rather than the parent compound, with Phase I trials initiated for a 2-Cyclohexylacetonitrile-derived dopamine D3 receptor partial agonist (NCT05677812). The compound's future appears most promising in specialty chemical production and as a template for fragment-based drug design, particularly for CNS-penetrant molecules.

• 70784-10-0([1,1'-Bicyclohexyl]-4-carbonitrile,4'-butyl-, (trans,trans)-)
• 80670-47-9(Cyclohexanecarbonitrile, 4-pentyl-, trans-)
• 65355-36-4([1,1'-Bicyclohexyl]-4-carbonitrile,4'-pentyl-, (trans,trans)-)
• 65355-35-3([1,1'-Bicyclohexyl]-4-carbonitrile, 4'-propyl-, (trans,trans)-)
• 27108-25-4(Bicyclo[2.2.1]heptane-2-acetonitrile,(1R,2S,4S)-rel-)
• 84219-05-6(Bicyclo[2.2.2]octane-1-acetonitrile, 4-butyl-)
• 70784-09-7([1,1'-Bicyclohexyl]-4-carbonitrile,4'-ethyl-, (trans,trans)-)
• 84963-32-6(Bicyclo[2.2.2]octane-2-carbonitrile,5-methyl-7-(1-methylethyl)-)
• 65355-37-5(trans,trans-4-Heptylbicyclohexyl-4-nitrile)
• 6303-65-7(Bicyclo[2.2.2]octane-2,3-dicarbonitrile,trans-)