Synthesis and Analgesic Activity of Amines Combining Diazaadamantane and Monoterpene Fragments


Journal Name: Medicinal Chemistry

Volume 13 , Issue 8 , 2017

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Graphical Abstract:


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 and 13C 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.

Keywords: Monoterpene, azaadamantane, adamantane, heterocyclic compounds, analgesic activity, acetic acid-induced writhing test, hot plate test.

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Article Details

Year: 2017
Published on: 08 November, 2017
Page: [773 - 779]
Pages: 7
DOI: 10.2174/1573406413666170525124316
Price: $65

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