Synthesis of new opioid derivatives with a propellane skeleton and their pharmacologies: Part 5, novel pentacyclic propellane derivatives with a 6-amide side chain

Bioorganic & Medicinal Chemistry
2015.0

Abstract

We designed and synthesized pentacyclic propellane derivatives with a 6-amide side chain to afford compounds with higher MOR/KOR ratio and lower sedative effects than nalfurafine. The obtained etheno-bridged derivative with a β-amide side chain, YNT-854, showed a higher MOR/KOR ratio than nalfurafine. YNT-854 also exhibited a higher dose ratio between the sedative effect and the analgesic effect than observed with nalfurafine, which may guide the future design of useful analgesics with a weaker sedative effect than nalfurafine.

Knowledge Graph

Similar Paper

Synthesis of new opioid derivatives with a propellane skeleton and their pharmacologies: Part 5, novel pentacyclic propellane derivatives with a 6-amide side chain
Bioorganic & Medicinal Chemistry 2015.0
Synthesis of new opioid derivatives with a propellane skeleton and their pharmacology: Part 1
Bioorganic & Medicinal Chemistry Letters 2011.0
Design, Synthesis, and Biological Evaluation of the Third Generation 17-Cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-[(4′-pyridyl)carboxamido]morphinan (NAP) Derivatives as μ/κ Opioid Receptor Dual Selective Ligands
Journal of Medicinal Chemistry 2019.0
Synthesis and Pharmacological Activities of 6-Glycine Substituted 14-Phenylpropoxymorphinans, a Novel Class of Opioids with High Opioid Receptor Affinities and Antinociceptive Potencies
Journal of Medicinal Chemistry 2011.0
Design, Synthesis, and Biological Evaluation of 17-Cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-[(4′-pyridyl)carboxamido]morphinan Derivatives as Peripheral Selective μ Opioid Receptor Agents
Journal of Medicinal Chemistry 2012.0
Synthesis and analgetic activity of some 5-aryl-2-azabicyclo[3.2.1]octanes
Journal of Medicinal Chemistry 1978.0
Syntheses of 4,6′-epoxymorphinan derivatives and their pharmacologies
Bioorganic & Medicinal Chemistry 2008.0
Synthesis and Pharmacology of a Novel κ Opioid Receptor (KOR) Agonist with a 1,3,5-Trioxazatriquinane Skeleton
ACS Medicinal Chemistry Letters 2014.0
Morphinan derivatives with an oxabicyclo[3.2.1]octane structure as dual agonists toward δ and κ opioid receptors
Bioorganic & Medicinal Chemistry 2022.0
Synthesis and Biological Evaluation of 14-Alkoxymorphinans. 18. N-Substituted 14-Phenylpropyloxymorphinan-6-ones with Unanticipated Agonist Properties:  Extending the Scope of Common Structure−Activity Relationships
Journal of Medicinal Chemistry 2003.0