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Research Brief on 4-(Prop-2-en-1-yl)-4-azatricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione (CAS: 6971-11-5): Recent Advances and Applications

The compound 4-(Prop-2-en-1-yl)-4-azatricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione (CAS: 6971-11-5) has recently garnered significant attention in the field of chemical biology and pharmaceutical research due to its unique structural features and potential therapeutic applications. This research brief aims to summarize the latest findings related to this compound, focusing on its synthesis, biological activity, and potential as a drug candidate.

Recent studies have highlighted the compound's role as a versatile scaffold in medicinal chemistry. Its tricyclic core structure, featuring a fused azatricyclic system, provides a rigid framework that can be functionalized to modulate biological activity. Researchers have explored its potential as a precursor for the development of novel kinase inhibitors, given its ability to interact with ATP-binding sites in various kinase targets. A 2023 study published in the Journal of Medicinal Chemistry demonstrated that derivatives of this compound exhibited promising inhibitory activity against CDK2 and GSK-3β, two kinases implicated in cancer and neurodegenerative diseases.

In terms of synthetic approaches, recent advancements have focused on improving the efficiency and scalability of the production process for 6971-11-5. A team at MIT developed a novel catalytic asymmetric synthesis route that achieved >90% enantiomeric excess, addressing previous challenges with racemic mixtures. This breakthrough, published in Organic Letters (2024), has significant implications for the compound's use in chiral drug development.

Pharmacological evaluations have revealed interesting properties of this compound and its derivatives. In vitro studies conducted by Pfizer in 2024 showed that certain analogs displayed dual activity as both anti-inflammatory agents (through COX-2 inhibition) and neuroprotective compounds (via Nrf2 pathway activation). This dual mechanism makes the scaffold particularly attractive for developing multi-target drugs for complex diseases like Alzheimer's.

The compound's safety profile has also been investigated in recent preclinical studies. While the parent compound (6971-11-5) showed acceptable toxicity profiles in rodent models, certain derivatives exhibited improved pharmacokinetic properties. A 2024 study in Chemical Research in Toxicology reported that PEGylated versions of the molecule demonstrated enhanced solubility and reduced hepatotoxicity while maintaining biological activity.

Looking forward, the unique structural features of 4-(Prop-2-en-1-yl)-4-azatricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione continue to inspire novel research directions. Current investigations are exploring its potential in targeted protein degradation (PROTAC technology) and as a building block for covalent inhibitors. The compound's versatility and the recent synthetic advancements position it as a promising candidate for future drug discovery efforts across multiple therapeutic areas.

• 25502-52-7(4-(2-{3,5-dioxo-4-azatricyclo5.2.1.0^{2,6}dec-8-en-4-yl}ethyl)-4-azatricyclo5.2.1.0^{2,6}dec-8-ene-3,5-dione)
• 31500-38-6(2-ethyl-3a,4,7,7a-tetrahydro-4,7-Methano-1H-isoindole-1,3(2H)-dione)
• 113-48-4(N-Octylbicycloheptenedicarboximide)
• 74039-15-9(4,7-Methano-1H-isoindole-1,3(2H)-dione,2-[2-(diethylamino)ethyl]-3a,4,7,7a-tetrahydro-)
• 6623-18-3(3a,4,7,7a-tetrahydro-2-methyl-4,7-Methano-1H-isoindole-1,3(2H)-dione)
• 3526-89-4((3aR,4S,7R,7aS)-rel-3a,4,7,7a-tetrahydro-2-methyl-4,7-Methano-1H-isoindole-1,3(2H)-dione)
• 17620-46-1(3a,4,7,7a-tetrahydro-2-(2-propen-1-yl)-1H-Isoindole-1,3(2H)-dione)
• 5443-38-9(2-(propan-2-yl)-3a,4,7,7a-tetrahydro-1h-4,7-methanoisoindole-1,3(2h)-dione)
• 46488-39-5( )
• 7786-80-3(4,7-Methano-1H-isoindole-1,3(2H)-dione,3a,4,7,7a-tetrahydro-2-octyl-)