Synthesis and analgesic activity of amines combining diazaadamantane and monoterpene fragments

Konstantin Ponomarev, Ekaterina Morozova, Alla Pavlova, Evgeniy Suslov, Dina Korchagina, Andrej Nefedov, Tat'yana Tolstikova, Konstantin Volcho, Nariman Salakhutdinov

    Research output: Contribution to journalArticlepeer-review

    4 Citations (Scopus)


    Background: It was found earlier that compounds combining diazaadamantane and monoterpene moieties possessed promising analgesic activity along with low acute toxicity and the lack of ulcerogenic activity. Objective: In this paper, new structural analogues of the most active compounds were synthesized and evaluated for their analgesic activity. Methods: Their structures were confirmed by various analytical methods, such as 1H and13C NMR, HRMS. All of them were evaluated for analgesic activity at a dose of 20 mg/kg or less using acetic acid-induced writhing test and hot plate test. Results: Some compounds showed analgesic activity in acetic acid-induced writhing test. One of the synthesized compounds demonstrated high analgesic activity in both tests with 46% effect in acetic acid-induced writhing test and 89% effect in hot plate test. Both structural fragments of this compound did not possess any analgesic effect at a dose of 20 mg/kg. Conclusion: Structure-activity relationships indicated that the most active compound combines fragments of (–)-myrtenal and 6-amino-5,7-dimethyl-1,3-diazaadamantane. Both parts of the molecule are important for demonstrating analgesic activity.

    Original languageEnglish
    Pages (from-to)773-779
    Number of pages7
    JournalMedicinal Chemistry
    Issue number8
    Publication statusPublished - 1 Dec 2017


    • Acetic acid-induced writhing test
    • Adamantane
    • Analgesic activity
    • Azaadamantane
    • Heterocyclic compounds
    • Hot plate test
    • Monoterpene
    • Administration, Oral
    • Monoterpenes/administration & dosage
    • Pain/chemically induced
    • Adamantane/administration & dosage
    • Structure-Activity Relationship
    • Amines/administration & dosage
    • Dose-Response Relationship, Drug
    • Acetic Acid
    • Analgesics/administration & dosage
    • Animals
    • Mice
    • Molecular Structure
    • Pain Measurement
    • azaadamantane
    • adamantane
    • analgesic activity
    • POTENT
    • acetic acid-induced writhing test
    • hot plate test
    • heterocyclic compounds


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