Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

C1′-Azacycloalkyl Hexahydrocannabinols

C1′-Azacycloalkyl Hexahydrocannabinols
Spyros P. Nikas, Marcus A. Tius, Naoyuki Shimada, Alexandros Makriyannis, Wen Zhang, Thanh C. Ho
We report the design, synthesis, and biological evaluation of a novel class of cannabinergic ligands, namely C1′-azacycloalkyl hexahydrocannabinols. Our synthetic approaches utilize an advanced common chiral intermediate triflate from which all analogues could be derived. Key synthetic steps involve microwave-assisted Liebeskind–Srogl C–C cross-coupling and palladium-catalyzed decarboxylative coupling reactions. The C1′-N-methylazetidinyl and C1′-N-methylpyrrolidinyl analogues were found to be high affinity ligands for the CB1 and CB2 cannabinoid receptors.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00988

DOI: 10.1021/acs.joc.7b00988

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