MiniBlock XT opens the door to sp3-rich tricyclic amine scaffolds through Diels-Alder reactions of azide-containing silyloxydienes
A library of 95 potential Sigma-1 and Sigma-2 inhibitors was swiftly generated taking advantage of the parallel synthesis capabilities of MiniBlock XT.
An elegant and divergent synthesis scheme was designed to prepare a series of analogs of potentially bioactive compounds. A 6,6,6-tricyclic amine building block was prepared through a Diels-Alder cycloaddition/Schmidt rearrangement domino sequence. Taking advantage of the MiniBlock XT unique capabilities in parallel synthesis, this scaffold was derivatized into 5 classes of analogs, for a total of 95 novel compounds. These structures will be screened against the Sigma-1 and Sigma-2 receptors to determine their biological activities.
Keywords:
Bioactive compounds, Diels-Alder, Schmidt, parallel synthesis
| Publication | Efficient access to sp3-rich tricyclic amine scaffolds through Diels-Alder reactions of azide-containing silyloxydienes |
| Authors | Michael C. McLeod, Jeffrey Aubé |
| Organization | Department of Medicinal Chemistry, University of Kansas |
| Source | Tetrahedron (2016), doi: 10.1016/j.tet.2016.03.016 |
| Date | 2016 |
| Reaction scheme |  |
| Full publication | http://www.sciencedirect.com/science/article/pii/S004040201630148X |
SiliCycle MiniBlock XT
The SiliCycle MiniBlock XT is an easy-to-operate parallel synthesis system designed for synthesis and screening reactions. Applications include synthesis of small organic molecules, optimization of critical process parameters, and screening for optimal reaction conditions.
- Parallel Synthesis
- Reaction Screening
- Catalyst Screening
- Reflux and Inerting
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