Synthesis, antiulcerative, and anti-inflammatory activities of new campholenic derivatives-1,3-thiazolidin-4-ones, 1,3-thiazolidine-2,4-diones, and 1,3-thiazinan-4-ones

In this paper, new thiazolidinones, thiazinanones, and thiazolidinediones based on a monoterpenoid (-)-campholenic aldehyde were synthesized and their antiulcer and anti-inflammatory activity was investigated. The thiazolidinones and thiazinanones containing a (-)-campholenic moiety have been shown...

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Published in:Chemical papers Vol. 75; no. 10; pp. 5503 - 5514
Main Authors: Borisova, Marina S., Ivankin, Dmitry I., Sokolov, Dmitry N., Luzina, Olga A., Rybalova, Tatjana V., Tolstikova, Tatjana G., Salakhutdinov, Nariman F.
Format: Journal Article
Language:English
Published: Warsaw Versita 01-10-2021
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Summary:In this paper, new thiazolidinones, thiazinanones, and thiazolidinediones based on a monoterpenoid (-)-campholenic aldehyde were synthesized and their antiulcer and anti-inflammatory activity was investigated. The thiazolidinones and thiazinanones containing a (-)-campholenic moiety have been shown to possess antiulcerogenic properties in indomethacin-induced ulcer test comparable to the activity of the reference drug omeprazole. None of the investigated thiazolidinediones showed antiulcerative activity in the test. One of the (-)-campholenic aldehyde-derived thiazolidinones has also demonstrated high anti-inflammatory activity on the histamine-induced inflammatory edema model similar to the activity of diclofenac. It is shown that changing a (-)-campholenic substituent for a linear aliphatic or a terpenic fragment with a pinane scaffold results in decreasing the pharmacological properties, though the (-)-campholenic moiety does not seem to make a key contribution to the pharmacological activity. Compounds 11 and 17 have been shown to exhibit antiulcer and anti-inflammatory action at a dose of 100 mg/kg.
ISSN:0366-6352
1336-9075
2585-7290
DOI:10.1007/s11696-021-01741-5