Synthesis and Analgesic Activity of Amines Combining Diazaadamantane and Monoterpene Fragments

Synthesis and Analgesic Activity of Amines Combining Diazaadamantane and Monoterpene Fragments Full article

Journal

Medicinal Chemistry
ISSN: 1573-4064 , E-ISSN: 1875-6638

Output data

Year: 2017, Volume: 13, Number: 8, Pages: 773-779 Pages count : 7 DOI: 10.2174/1573406413666170525124316

Tags

Monoterpene; azaadamantane; adamantane; heterocyclic compounds; analgesic activity; acetic acid-induced writhing test; hot plate test

Authors

Ponomarev Konstantin ¹ , Morozova Ekaterina ¹ , Pavlova Alla ¹ , Suslov Evgeniy ¹ , Korchagina Dina ¹ , Nefedov Andrej ¹ , Tolstikova Tat'yana ^1,2 , Volcho Konstantin ^1,2 , Salakhutdinov Nariman ^1,2

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Novosibirsk 630090, Russia

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 H-1 and C-13 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.

Ponomarev K. , Morozova E. , Pavlova A. , Suslov E. , Korchagina D. , Nefedov A. , Tolstikova T. , Volcho K. , Salakhutdinov N.
Synthesis and Analgesic Activity of Amines Combining Diazaadamantane and Monoterpene Fragments
Medicinal Chemistry. 2017. V.13. N8. P.773-779. DOI: 10.2174/1573406413666170525124316 WOS Scopus РИНЦ OpenAlex

Published print:

Nov 8, 2017

Web of science:	WOS:000415068900009
Scopus:	2-s2.0-85029551777
Elibrary:	35491919
OpenAlex:	W2619100693

DB	Citing
Web of science	12
Scopus	10
Elibrary	12
OpenAlex	11