Morphinans

Casy, A. F.; Parfitt, Robert T.

doi:10.1007/978-1-4899-0585-7_3

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2007

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“…To synthesize the nor-BNI analog without the 4,5-epoxy bridge (compound 4), the reaction of morphinan 2 32) with hydrazine dihydrochloride was carried out under aerobic conditions (Chart 1). Compound 3 having 5Ј-keto group was obtained concomitantly with starting compound 2 and other unidentified compounds, but not the objective compound 4, which was the precursor of the compound 1.…”

Section: Resultsmentioning

confidence: 99%

Catalytic Aerobic Oxidation of nor-Binaltorphimine (nor-BNI) Analogs without 4,5-Epoxy Bridge Affords a More Selective Ligand for .KAPPA. Opioid Receptor than the Representative .KAPPA. Antagonist nor-BNI

Osa

Ida

Fujii

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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An analog of nor-binaltorphimine (nor-BNI) without the 4,5-epoxy bridge, 17,17-bis(cyclopropylmethyl)-6,6,7,7-tetrahydro-6,6-imino-14b b,14a a-dihydroxy-3,3-dimethoxy-7,7-bimorphinan (4), which was the precursor of the designed compound 1 as a selective k k 3 opioid receptor antagonist, was catalytically oxidized with oxygen in the presence of platinum to give the 5-oxo derivative 3 with some other oxidized products. Morphinan derivatives without the 4,5-epoxy moiety were labile to oxygen, although the corresponding 4,5-epoxymorphinan derivatives resisted aerobic oxidation. One of the oxidized nor-BNI analogs without 4,5-epoxy bridge, compound 18, showed high affinity and selectivity for k k opioid receptor.

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Section: Resultsmentioning

confidence: 99%