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4-Aminocyclopentane-1,3-diols as Platforms for Diversity: Synthesis of Anandamide Analogs

Zohrabi-Kalantari, Vida ; Jarrahian, Abbas ; Bissantz, Caterina ; Bergstrom, Donald E ; Barker, Eric L ; Link, Andreas

Medicinal chemistry (Shp-sariqah, United Arab Emirates), 2013-09, Vol.9 (6), p.881-888 [Periódico revisado por pares]

Netherlands: Bentham Science Publishers Ltd

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Título:
4-Aminocyclopentane-1,3-diols as Platforms for Diversity: Synthesis of Anandamide Analogs
Autor: Zohrabi-Kalantari, Vida ; Jarrahian, Abbas ; Bissantz, Caterina ; Bergstrom, Donald E ; Barker, Eric L ; Link, Andreas
Assuntos: Amines - chemistry ; Arachidonic Acids - chemical synthesis ; Arachidonic Acids - chemistry ; Combinatorial Chemistry Techniques ; Cyclopentanes - chemistry ; Drug Design ; Endocannabinoids - chemical synthesis ; Endocannabinoids - chemistry ; Hydrophobic and Hydrophilic Interactions ; Models, Molecular ; Molecular Structure ; Polyunsaturated Alkamides - chemical synthesis ; Polyunsaturated Alkamides - chemistry ; Small Molecule Libraries ; Stereoisomerism
É parte de: Medicinal chemistry (Shp-sariqah, United Arab Emirates), 2013-09, Vol.9 (6), p.881-888
Notas: ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
Descrição: 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.
Editor: Netherlands: Bentham Science Publishers Ltd
Idioma: Inglês

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4-Aminocyclopentane-1,3-diols as Platforms for Diversity: Synthesis of Anandamide Analogs

Zohrabi-Kalantari, Vida ; Jarrahian, Abbas ; Bissantz, Caterina ; Bergstrom, Donald E ; Barker, Eric L ; Link, Andreas

Netherlands: Bentham Science Publishers Ltd

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