21020-35-9

Usage

Chemical Properties

Off-White Solid

Uses

(-)-Butorphanol intermediate.

Upstream product

• 107-21-1 ethylene glycol 
• 3442-60-2 (4bR,8aS,9R)-8a-hydroxy-3-methoxy-11-methyl-8,8a,9,10-tetrahydro-5H-9,4b-(epiminoethano)phenanthren-6(7H)-one 
• 1043876-55-6 C₂₃H₃₁NO₄ 
• 50-00-0 formaldehyd 
• 1612-45-9 C₁₉H₂₅NO₄ 
• 21030-81-9 14-hydroxy-3-methoxy-17-methyl-4-phenoxy-morphinan-6-one 
• 21020-34-8 6,6-ethane-1,2-diyldioxy-3-methoxy-17-methyl-4-phenoxy-morphinan-14-ol 

Relevant academic research and scientific papers

AZAMOPHINAN DERIVATIVES AND USE THEREOF

The application is directed to compounds of Formula (I) and pharmaceutically acceptable salts and solvates thereof, wherein R1, R2, R3, R4, Y, and Z are defined as set forth in the specification. The invention i

Synthesis of quinolinomorphinan derivatives as highly selective δ opioid receptor ligands

We have reported previously the novel δ opioid agonist KNT-127 which showed high affinity and selectivity for the δ receptor. Moreover, the analgesic effect of subcutaneously administered KNT-127 was more potent than that of a prototypical δ agonist (-)-TAN-67 in the acetic acid writhing test. This study of the structure-activity relationship of KNT-127 derivatives focused on the introduction of substituents onto the 5′-, 6′-, 7′- or 8′-position of the quinoline ring and revealed that many derivatives with 5′- or 8′-substituents showed high affinities and selectivities for the δ receptor. Especially, SYK-153 with an 8′-OH group showed the highest affinity and the most balanced and highest selectivity for the δ receptor among the synthesized compounds.

Design and synthesis of KNT-127, a δ-opioid receptor agonist effective by systemic administration

We have reported previously the novel δ-opioid agonist, SN-28, which was more potent in in vitro assays than the prototype δ-agonists, TAN-67 and SNC-80. However, when administered by subcutaneous injection, this compound showed no analgesic effect at dosages greater than 30 mg/kg in the acetic acid writhing test. We speculated that SN-28 was not effective in the test because the presence of the charged ammonium groups prevented its penetration through the blood-brain barrier. On the basis of our proposal, we designed the novel δ-agonist, KNT-127, which was effective with systemic administration.

Synthesis and opioid receptor activity of indolopropellanes

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.