Synthesis of a novel 4,6′-epoxymorphinan derivative and a highly strained novel conjugated ketone |
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Authors: | Toru Nemoto |
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Affiliation: | School of Pharmacy, Kitasato University 5-9-1, Shirokane, Minatoku, Tokyo 108-8641, Japan |
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Abstract: | A modification of the 4,5-epoxymorphinan skeleton of naltrexone was carried out to improve the potency and the selectivity of the ligand for an opioid receptor subtype. As one of the modified structures, we newly designed and synthesized a novel 7-membered ring ether derivative, which had an inserted OCH2 group between the 4- and 6-positions of the morphinan skeleton. The derivative with a 7-membered ring ether, 4,6′-epoxymorphinan, has a more fixed chair form than the 4,5-epoxymorphinan. In addition, we found a new cleavage reaction of the 4,5-epoxy ring in naltrexone, and also obtained a highly strained novel conjugated ketone. |
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Keywords: | Opioid Naltrexone 4,6&prime -Epoxymorphinan Analgesics |
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