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dc.contributor.authorLozama, Anthony
dc.contributor.authorCunningham, Christopher W.
dc.contributor.authorCaspers, Michael J.
dc.contributor.authorDouglas, Justin T.
dc.contributor.authorDersch, Christina M.
dc.contributor.authorRothman, Richard B.
dc.contributor.authorPrisinzano, Thomas E.
dc.date.accessioned2017-01-11T20:12:56Z
dc.date.available2017-01-11T20:12:56Z
dc.date.issued2011-02-21
dc.identifier.citationLozama, Anthony, Christopher W. Cunningham, Michael J. Caspers, Justin T. Douglas, Christina M. Dersch, Richard B. Rothman, and Thomas E. Prisinzano. "Opioid Receptor Probes Derived from Cycloaddition of the Hallucinogen Natural Product Salvinorin A." Journal of Natural Products 74.4 (2011): 718-26.en_US
dc.identifier.urihttp://hdl.handle.net/1808/22585
dc.description.abstractAs part of our continuing efforts toward more fully understanding the structure−activity relationships of the neoclerodane diterpene salvinorin A, we report the synthesis and biological characterization of unique cycloadducts through [4+2] Diels−Alder cycloaddition. Microwave-assisted methods were developed and successfully employed, aiding in functionalizing the chemically sensitive salvinorin A scaffold. This demonstrates the first reported results for both cycloaddition of the furan ring and functionalization via microwave-assisted methodology of the salvinorin A skeleton. The cycloadducts yielded herein introduce electron-withdrawing substituents and bulky aromatic groups into the C-12 position. Kappa opioid (KOP) receptor space was explored through aromatization of the bent oxanorbornadiene system possessed by the cycloadducts to a planar phenyl ring system. Although dimethyl- and diethylcarboxylate analogues 5 and 6 retain some affinity and selectivity for KOP receptors and are full agonists, their aromatized counterparts 13 and 14 have reduced affinity for KOP receptors. The methods developed herein signify a novel approach toward rapidly probing the structure−activity relationships of furan-containing natural products.en_US
dc.publisherJournal of Natural Productsen_US
dc.rightsCopyright © 2011 The American Chemical Society and American Society of Pharmacognosyen_US
dc.titleOpioid Receptor Probes Derived from Cycloaddition of the Hallucinogen Natural Product Salvinorin Aen_US
dc.typeArticleen_US
kusw.kuauthorDouglas, Justin T.
kusw.kudepartmentMSG-Nuclear Magnetic Resonanceen_US
dc.identifier.doi10.1021/np1007872en_US
dc.identifier.orcidhttps://orcid.org/0000-0002-4468-2213
kusw.oaversionScholarly/refereed, publisher versionen_US
kusw.oapolicyThis item meets KU Open Access policy criteria.en_US
dc.rights.accessrightsopenAccess


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