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

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

Volume: 9 Issue: 6

Author(s): Vida Zohrabi-Kalantari, Abbas Jarrahian, Caterina Bissantz, Donald E. Bergstrom, Eric L. Barker and Andreas Link

Affiliation:

Keywords: Cannabinoids, Cyclopentane, Diversity, Epoxide, Stereocontrolled Synthesis, Transport Inhibitors.

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.

Cite this article as:

Zohrabi-Kalantari Vida, Jarrahian Abbas, Bissantz Caterina, Bergstrom E. Donald, Barker L. Eric and Link Andreas, 4-Aminocyclopentane-1,3-diols as Platforms for Diversity: Synthesis of Anandamide Analogs, Medicinal Chemistry 2013; 9 (6) . https://dx.doi.org/10.2174/1573406411309060013