4-Aminocyclopentane-1,3-diols as Platforms for Diversity: Synthesis of Anandamide Analogs
| Autor: | Eric L. Barker, Abbas Jarrahian, Vida Zohrabi-Kalantari, Caterina Bissantz, Donald E. Bergstrom, Andreas Link |
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| Rok vydání: | 2013 |
| Předmět: |
Models
Molecular Natural product Cyclopentadiene Molecular Structure Combinatorial Chemistry Techniques Polyunsaturated Alkamides Stereochemistry Small Molecule Libraries Stereoisomerism Arachidonic Acids Cyclopentanes Anandamide Ring (chemistry) chemistry.chemical_compound chemistry Drug Design Drug Discovery Molecule Amines Hydrophobic and Hydrophilic Interactions Endocannabinoids |
| Zdroj: | Medicinal Chemistry. 9:881-888 |
| ISSN: | 1573-4064 |
| DOI: | 10.2174/1573406411309060013 |
| Popis: | Starting from cyclopentadiene, two racemic mixtures of 4-aminocyclopentane-1,3-diols were prepared in 8 steps and characterized. Structure determination proved the anticipated trans-orientation of the two oxygen atoms with respect to the plane of the ring. The fragment-like new compounds are small and hydrophilic, devoid of rotatable bonds, and offer stereochemically defined attachment points for substituents. Thus, these platforms for diversity are suitable starting points for the construction of combinatorial libraries of lead-like 4-amidocyclopentane-1,3-diols or natural product analogs. As a proof of concept, cyclopentanoid anandamide analogs were prepared using these molecular platforms and evaluated as tools for the investigation of unresolved issues in the molecular biology of anandamide. |
| Databáze: | OpenAIRE |
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