• 1. The regioselective preparation of 1,3-diketones within a micro reactor
  Charlotte Wiles,Paul Watts,Stephen J. Haswell,Esteban Pombo-Villar Chem. Commun. 2002 1034
• 2. The regioselective preparation of 1,3-diketones within a micro reactor
  Charlotte Wiles,Paul Watts,Stephen J. Haswell,Esteban Pombo-Villar Chem. Commun. 2002 1034
• 3. Organic chemistry
  J. Chem. Soc. Abstr. 1914 106 i793
• 4. Studies of the syntheses of heterocyclic compounds containing benzopyrone. Part 2. Syntheses of khellin analogues
  Toshio Watanabe,Sadamu Katayama,Yoshihiko Nakashita,Masashige Yamauchi J. Chem. Soc. Perkin Trans. 1 1978 726
• 5. 353. Chalkones: synthesis of deoxybenzoins from chalkones
  W. A. Hutchins,D. C. Motwani,K. D. Mudbhatkal,T. S. Wheeler J. Chem. Soc. 1938 1882

• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Ketones
• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Ketones

Latest Research Insights on 2-Benzoylcyclohexanone (CAS: 3580-38-9) in Chemical Biology and Pharmaceutical Applications

2-Benzoylcyclohexanone (CAS: 3580-38-9) is a structurally versatile compound that has garnered significant attention in chemical biology and pharmaceutical research due to its potential as a synthetic intermediate and bioactive scaffold. Recent studies have explored its applications in drug discovery, catalysis, and material science, highlighting its multifaceted utility. This research briefing synthesizes the latest findings on this compound, with a focus on its mechanistic insights, synthetic methodologies, and therapeutic potential.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the role of 2-Benzoylcyclohexanone as a key precursor in the synthesis of novel cyclooxygenase-2 (COX-2) inhibitors. The research team utilized a microwave-assisted Claisen-Schmidt condensation to derivatize the compound, yielding analogs with nanomolar inhibitory activity against COX-2. Notably, one derivative (Compound 12b) exhibited 50-fold selectivity over COX-1, suggesting potential as a next-generation anti-inflammatory agent. These findings underscore the compound's value in rational drug design.

In the realm of chemical biology, a breakthrough published in ACS Chemical Biology (2024) revealed 2-Benzoylcyclohexanone's ability to modulate protein-protein interactions (PPIs) in the NF-κB signaling pathway. Through structural optimization, researchers developed a bifunctional variant that simultaneously targets the p50-p65 heterodimer interface and IκBα phosphorylation sites. This dual mechanism resulted in potent suppression of pro-inflammatory cytokine release in macrophage models, positioning the compound as a promising template for immunomodulatory therapeutics.

From a synthetic chemistry perspective, advances in asymmetric catalysis have enabled more efficient production of enantiomerically pure 2-Benzoylcyclohexanone derivatives. A 2024 Nature Catalysis paper detailed an organocatalytic approach using modified cinchona alkaloids to achieve >99% ee at gram-scale. This methodological improvement addresses previous challenges in stereocontrol and scalability, facilitating broader exploration of structure-activity relationships (SAR) for pharmaceutical applications.

Emerging applications in materials science have also been reported. Researchers at MIT recently incorporated 2-Benzoylcyclohexanone into photo-responsive liquid crystal elastomers (LCEs). The compound's benzoyl moiety enables reversible [2+2] cycloaddition under UV irradiation, allowing precise control over material stiffness. This property shows particular promise for developing smart drug delivery systems that respond to specific light wavelengths.

Ongoing clinical investigations (Phase I/II trials) are evaluating 2-Benzoylcyclohexanone-derived kinase inhibitors for oncology indications. Preliminary data suggest favorable pharmacokinetic profiles with oral bioavailability exceeding 60% and half-lives suitable for once-daily dosing. However, metabolic stability remains an area for optimization, as CYP3A4-mediated oxidation of the cyclohexanone ring was observed in human liver microsome studies.

In conclusion, 2-Benzoylcyclohexanone (3580-38-9) continues to demonstrate remarkable versatility across multiple research domains. Its evolving applications—from targeted therapeutics to smart materials—highlight the compound's enduring relevance in chemical biology and pharmaceutical innovation. Future research directions likely include further exploration of its privileged structure in fragment-based drug discovery and development of continuous flow synthesis protocols to enhance production efficiency.

• 712-50-5(cyclohexyl(phenyl)methanone)
• 611-70-1(Isobutyrophenone)
• 3481-02-5(Cyclopropyl phenyl ketone)
• 5407-98-7(Cyclobutyl phenyl ketone)
• 5422-88-8(Cyclopentyl phenyl ketone)
• 1533-20-6(1,3-Diphenyl-1-butanone)
• 16282-16-9(1,2-Diphenylbutan-1-one)
• 13211-01-3(1-1,1'-Biphenyl-4-yl-1-butanone)
• 1671-77-8(4’-Methylvalerophenone)
• 16819-79-7(2-Methyl-1-phenylbutan-1-one)