73986-27-3Relevant articles and documents
Effects of substitution on the pyrrole N atom in derivatives of tetrahydronaltrindole, tetrahydrooxymorphindole, and a related 4,5-epoxyphenylpyrrolomorphinan
Srivastava, Sanjay K.,Shefali,Miller, Carl N.,Aceto, Mario D.,Traynor, John R.,Lewis, John W.,Husbands, Stephen M.
, p. 6645 - 6648 (2004)
The effect of substitution of the pyrrolo- and indolo-N atoms in tetrahydronaltrindole (TNTI), tetrahydrooxymorphindole (TOMI), and 17-cyclopropylmethyl-3,14-dihydroxy-4,5-epoxy-4′-phenyl-6,7:2′, 3′-pyrrolomorphinan (4) is reported. In opioid functional a
Michael reactions of benzylimines derived from morphinan-6-ones: Synthesis of pyrrolo- and pyridinomorphinans
Shefali,Srivastava, Sanjay K.,Hall, Lee D.,Lewis, John W.,Husbands, Stephen M.
, p. 1790 - 1799 (2002)
The benzylimines 15 derived from oxymorphones 14 and generated in situ reacted with Michael acceptors (methyl methacrylate, maleic anhydride, and α-methylene-γ-butyrolactone) to give opioid ligands 16, 17, and 19-21 having pyrrole- or pyridine-derived ring systems (see Scheme 3). The product of the reaction with maleic anhydride displayed a surprising preference for the 2-hydroxypyrrole form 19 rather than for the tautomeric 1,6-dihydro-2H-pyrrol-2-one form 24, resulting from the stability of the C(6)=C(7) bond in oxymorphone and related structures.
4'-Arylpyrrolomorphinans: effect of a pyrrolo-N-benzyl substituent in enhancing delta-opioid antagonist activity.
Srivastava, Sanjay K,Husbands, Stephen M,Aceto, Mario D,Miller, Carl N,Traynor, John R,Lewis, John W
, p. 537 - 540 (2002)
A new method for the preparation of N-benzylpyrrolomorphinans has been developed. Thus Michael reaction of the benzylimines of oxycodones and oxymorphones with nitrostyrenes gave a series of 4'-aryl-N-benzylpyrrolomorphinans. These were selective delta an
Tuned-affinity bivalent ligands for the characterization of opioid receptor heteromers
Harvey, Jessica H.,Long, Darcie H.,Whistler, Jennifer L.,England, Pamela M.
supporting information, p. 640 - 644,5 (2020/08/31)
Opioid receptors, including the μ- and δ-opioid receptors (MOR and DOR), are important targets for the treatment of pain. Although there is mounting evidence that these receptors form heteromers, the functional role of the MOR/DOR heteromer remains unresolved. We have designed and synthesized bivalent ligands as tools to elucidate the functional role of the MOR/DOR heteromer. Our ligands (L2 and L4) are comprised of a compound with low affinity at the DOR tethered to a compound with high affinity at the MOR, with the goal of producing ligands with "tuned affinity" at MOR/DOR heteromers as compared to DOR homomers. Here, we show that both L2 and L4 demonstrate enhanced affinity at MOR/DOR heteromers as compared to DOR homomers, thereby providing unique pharmacological tools to dissect the role of the MOR/DOR heteromer in pain.
