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9 alpha- and 9 beta-Hydroxyphenylmorphans.

H Awaya, E L May, A E Jacobson

    Journal of Pharmaceutical Sciences
    |December 1, 1984
    PubMed
    Summary
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    This study investigated the antinociceptive properties of novel morphan analogues. The phenolic analogue (III) demonstrated strong pain relief and supported morphine dependence, unlike its diastereoisomer (VII).

    Area of Science:

    • Medicinal Chemistry
    • Pharmacology
    • Organic Synthesis

    Background:

    • Morphan derivatives are explored for their potential analgesic properties.
    • Understanding structure-activity relationships is crucial for developing effective pain therapeutics.
    • Morphine dependence and withdrawal symptoms are significant challenges in pain management.

    Purpose of the Study:

    • To synthesize and evaluate the antinociceptive activity of a phenolic morphan analogue (III) and its diastereoisomer (VII).
    • To assess the compounds' ability to support morphine dependence in rhesus monkeys.
    • To elucidate the stereochemical orientation of hydroxyl groups influencing biological activity.

    Main Methods:

    • Platinum-oxide catalyzed hydrogenation of 5-m-methoxyphenyl-2-methyl-9-oxomorphan (I) to yield racemate (II).

    Related Experiment Videos

  • Synthesis of phenolic analogue (III) and its di-O-acetyl derivative (VI).
  • Stereoselective synthesis of diastereoisomer (VII) via methobromide intermediate (IV), methyl bromide extrusion, and O-demethylation.

    • Main Results:

    • Phenolic analogue (III) exhibited potent antinociceptive effects and fully supported morphine dependence in rhesus monkeys.
    • The di-O-acetyl derivative (VI) showed a similar activity profile to (III).
    • Diastereoisomer (VII) was largely inactive in antinociception and failed to suppress withdrawal symptoms.

    Conclusions:

    • The stereochemistry at the C-9 position significantly impacts the antinociceptive activity and opioid-like properties of these morphan derivatives.
    • Compound (III) represents a promising lead for developing novel analgesics with potential to manage opioid dependence.
    • Further research into C-9 hydroxyl group orientation is warranted for optimizing drug design.