Synthetic approaches to isocarbacyclin and analogues as potential neuroprotective agents against ischemic stroke.

Bioorg Med Chem

Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, Greensboro 27402, USA. Electronic address:

Published: January 2019

Isocarbacyclin is a valuable synthetic analogue of prostacyclin with potential neuroprotective effects for the treatment of ischemic stroke. Herein, we describe the synthesis of isocarbacyclin and bicyclic analogues in only 7-10 steps, with the ω-side chain diversified at a late stage. A combination of new reaction design, function-oriented synthesis, and late-stage diversification led to a series of compounds that were tested for their neuroprotective activities. Efforts toward the synthesis of tricyclic analogues of isocarbacyclin, using the same combination of metal-catalyzed reactions, is also described.

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http://dx.doi.org/10.1016/j.bmc.2018.12.010DOI Listing

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