153567-11-4Relevant articles and documents
Delta opioid binding selectivity of 3-ether analogs of naltrindole
Coop, Andrew,Pinto, Julia,Wang, Lijuan,McCullough, Karen,Rothman, Richard B.,Dersch, Christine,Jacobson, Arthur E.,Rice, Kenner C.
, p. 3435 - 3438 (1999)
Masking of the 3-phenol of naltrindole as a range of ethers caused a decrease in binding affinity at all three opiate receptors (μ, κ, δ), however for the methyl ether, the reduction in affinity at both μ and κ was greater than at δ, thereby increasing δ
Design, synthesis, and preliminary evaluation of a potential synthetic opioid rescue agent
Baynard, Caroline,Butelman, Eduardo R.,Hedrick, Sidnee L.,Horn, Jamie,Jackson, Karen,Kaska, Sophia,Kreek, Mary Jeanne,Leggas, Markos,Luo, Dan,Niloy, Kumar Kulldeep,Prisinzano, Thomas E.,Sarma, Rupam
, (2021/09/14)
Background: One of the most prominent opioid analgesics in the United States is the high potency agonist fentanyl. It is used in the treatment of acute and chronic pain and as an anesthetic adjuvant. When used inappropriately, however, ingestion of just a
Preparation method for bromomethyl naltrexone
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Paragraph 0025; 0035; 0066; 0067; 0068, (2017/01/19)
The invention specifically relates to a preparation method for bromomethyl naltrexone, belonging to the field of pharmaceutical chemicals. According to the invention, bromomethyl naltrexone is prepared from an intermediate, i.e., O-benzyl-N-bromomethyl na
An efficient synthesis of 3-OBn-6β,14-epoxy-bridged opiates from naltrexone and identification of a related dual MOR inverse agonist/KOR agonist
Martin, David J.,Fitzmorris, Paul E.,Deveau, Amy M.,Li, Bo,Ayestas, Mario,Sally, Ellicott J.,Dersch, Christina M.,Rothman, Richard B.
supporting information, p. 6801 - 6805,5 (2020/09/02)
In an effort to better understand the conformational preferences that inform the biological activity of naltrexone and related naltrexol derivatives, a new synthesis of the restricted analog 3-OBn-6β,14-epoxymorphinan 4 is described. 4 was synthesized starting from naltrexone in 50% overall yield, proceeding through the OBn-6α-triflate intermediate 8. Key steps to the synthesis include benzylation (96% yield), reduction (90% yield, α:β:3:2), followed by a one-pot triflation/displacement sequence (96% yield) to yield the desired bridged epoxy derivative 4. X-ray crystallographic analysis of intermediate 3-OBn-6α-naltrexol 7a supports population of the key boat conformation required for the epoxy ring closure. We also report that the 6β-mesylate 10-a high affinity opioid receptor ligand, the epimeric derivative of 11, and an analog of 12-functions as an inverse agonist at the mu opioid receptor using herkinorin pre-conditioned cells and an agonist at the kappa opioid receptor when evaluated in independent in vitro [ 35S]-GTP-γ-S assays.
