title: 4-Aminocyclopentane-1,3-diols as platforms for diversity: synthesis of anandamide analogs.
abstract: 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.
authors.affiliation: Institute of Pharmacy, Ernst- Moritz-Arndt-University, Friedrich-Ludwig-Jahn-Str. 17, 17487 Greifswald, Germany.
authors.forename: Vida
authors.initials: V
authors.lastname: Zohrabi-Kalantari
authors.forename: Abbas
authors.initials: A
authors.lastname: Jarrahian
authors.forename: Caterina
authors.initials: C
authors.lastname: Bissantz
authors.forename: Donald E
authors.initials: DE
authors.lastname: Bergstrom
authors.forename: Eric L
authors.initials: EL
authors.lastname: Barker
authors.forename: Andreas
authors.initials: A
authors.lastname: Link
mesh_terms: D000588:Amines / Q000737:chemistry*; D001095:Arachidonic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D003517:Cyclopentanes / Q000737:chemistry*; D015195:Drug Design; D063388:Endocannabinoids / Q000138:chemical synthesis* / Q000737:chemistry; D057927:Hydrophobic and Hydrophilic Interactions; D008958:Models, Molecular; D015394:Molecular Structure; D053284:Polyunsaturated Alkamides / Q000138:chemical synthesis* / Q000737:chemistry; D054852:Small Molecule Libraries; D013237:Stereoisomerism
chemical_list: D000588:Amines; D001095:Arachidonic Acids; D003517:Cyclopentanes; D063388:Endocannabinoids; D053284:Polyunsaturated Alkamides; D054852:Small Molecule Libraries; C078814:anandamide