ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

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

Marina S. Borisova, Dmitry I. Ivankin, Dmitry N. Sokolov, Olga A. Luzina, Tatjana V. Rybalova, Tatjana G. Tolstikova, and Nariman F. Salakhutdinov

N N Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, Russia

E-mail: mborisova@nioch.nsc.ru

Received: 12 February 2021  Accepted: 9 June 2021

Abstract:

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.

Keywords: Antiulcer; Anti-inflammatory; (-)-Campholenic aldehyde; Thiazolidinones; Thiazinanones; Thiazolidinediones

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-021-01741-5

Chemical Papers 75 (10) 5503–5514 (2021)