noroxymorphone and cyclopropane

noroxymorphone has been researched along with cyclopropane* in 1 studies

Other Studies

1 other study(ies) available for noroxymorphone and cyclopropane

Article	Year
Synthesis of N-isobutylnoroxymorphone from naltrexone by a selective cyclopropane ring opening reaction. Bioorganic & medicinal chemistry letters, 2008, Sep-15, Volume: 18, Issue:18 Selective ring opening reaction of the N-cyclopropylmethyl group in naltrexone (1d) was effected in the presence of platinum (IV) oxide and hydrobromic acid under a hydrogen atmosphere at rt to selectively afford N-isobutyl derivative 10. The binding affinity of N-i-Bu derivative 10 for opioid receptors was 11-17 times less than that of the corresponding N-CPM compound, naltrexone (1d). However, compound 10 showed dose-dependent analgesic effects. Contrary to expectations based on previous structure-activity relationship studies for a series of N-substituted naltrexone derivatives that compound 10 would be an opioid antagonist, 10 showed dose-dependent analgesia in the mouse acetic acid writhing test (ED(50): 5.05 mg/kg, sc), indicating it was an opioid agonist. This finding may have a great influence on the drug design of opioid agonists. Topics: Acetic Acid; Analgesics, Opioid; Animals; Cyclopropanes; Dose-Response Relationship, Drug; Mice; Molecular Structure; Morphinans; Naltrexone; Receptors, Opioid	2008

Article

Year

Synthesis of N-isobutylnoroxymorphone from naltrexone by a selective cyclopropane ring opening reaction.

Bioorganic & medicinal chemistry letters, 2008, Sep-15, Volume: 18, Issue:18

Selective ring opening reaction of the N-cyclopropylmethyl group in naltrexone (1d) was effected in the presence of platinum (IV) oxide and hydrobromic acid under a hydrogen atmosphere at rt to selectively afford N-isobutyl derivative 10. The binding affinity of N-i-Bu derivative 10 for opioid receptors was 11-17 times less than that of the corresponding N-CPM compound, naltrexone (1d). However, compound 10 showed dose-dependent analgesic effects. Contrary to expectations based on previous structure-activity relationship studies for a series of N-substituted naltrexone derivatives that compound 10 would be an opioid antagonist, 10 showed dose-dependent analgesia in the mouse acetic acid writhing test (ED(50): 5.05 mg/kg, sc), indicating it was an opioid agonist. This finding may have a great influence on the drug design of opioid agonists.

Topics: Acetic Acid; Analgesics, Opioid; Animals; Cyclopropanes; Dose-Response Relationship, Drug; Mice; Molecular Structure; Morphinans; Naltrexone; Receptors, Opioid

2008