6199-38-8Relevant articles and documents
Opioid affinity and selectivity of 4-hydroxy-3-methoxyindolomorphinan analogues related to naltrindole
Coop, Andrew,Rothman, Richard B.,Dersch, Christina,Partilla, John,Porreca, Frank,Davis, Peg,Jacobson, Arthur E.,Rice, Kenner C.
, p. 1673 - 1679 (1999)
To investigate the effect of the introduction of a 4-phenolic substituent on the δ opioid affinity and selectivity of the indolomorphinans, a range of 4-phenolic analogues of naltrindole were prepared and evaluated in in vitro assays. Although the majority of the ligands displayed poor affinity for all three opioid receptors (μ, κ, δ), 17-cyclopropylmethyl-6,7-didehydro-4-hydroxy-3-methoxy-6,7:2',3'- indolomorphinan (13) was an exception, displaying excellent 5 binding selectivity (δ K(i) = 7 nM, μ/δ = 1900, μ/κ = 1130). GTP-χ-S functional assays showed 13 to be a selective δ antagonist, albeit with lower potency than naltrindole. Although the reason for the unique profile of 13 could not be determined, these results validate our approach of introducing groups into the indolomorphinans that are known to reduce μ activity, to obtain increased δ selectivity.
Synthesis and opioid receptor activity of indolopropellanes
Li, Fuying,Gaob, Linghuan,Yin, Chenlei,Chen, Jie,Liu, Jinggen,Xie, Xin,Zhang, Ao
scheme or table, p. 4603 - 4606 (2010/04/29)
A series of skeletal rearranged indolomorphinans 7a-d were obtained by N-demethylation of 3-methoxy-N-methyl-14-hydroxymorphinan-6-one 12 followed by N-realkylation, reduction and Fischer indole cyclization. The structure of the novel skeleton was confirmed by X-ray analysis. These new indoles displayed moderate binding affinity and selectivity at the μ receptor, with compound 7b showing the highest affinity at this receptor with a Ki value of 40 nM, and 6- and 25-fold selectivity against δ and κ receptors, respectively. Function assays showed that indolopropellanes 7b and 7c possessed full agonistic activity at all the opioid receptors indicating a different interaction model existed.
Formamidinesulfinic acid reduction of dihydrocodeinone derivatives
Brine,Boldt,Coleman,et al.
, p. 1555 - 1557 (2007/10/09)
Treatment of dihydrocodeinone (1f) with formamidinesulfinic acid afforded mixtures of dihydrothebainone (3a) dihydroisothebainol dihydroisothenainol (4a) under both homogeneous and heterogeneous conditions. Similar treatment of 14-hydroxydihydrocodeinone
