Synthesis, the antioxidant and antibacterial activity of fluoroalkyl substituted thiazolidinones and thiazinanones incorporating an aminophosphonate or aminocarboxylate fragment

I. P. Yelenich, Yu. V. Rassukana, Ya. Ya. Khomutnyk, M. M. Kornet, O. A. Brazhko, A. D. Synytsya, P. P. Onys’ko

Abstract


2-R-2-RF-4-оxo-thiazolidines, thiazinanes, and bezothiazinanes incorporating a fragment of aminophosphonic or aminocarboxylic acid and a fluoroalkyl group at C-2 atom of the heterocycle have been prepared by cyclocondensation of the corresponding iminophosphonates or iminocarboxylates, RFCH(R)=NH [R = (EtO)2P(O), COOMe, RF = CF3, CHF2], with mercaptoacetic, 3-mercaptopropionic or thiosalicylic acid. The primary screening of the compounds on the antioxidant and antibacterial activity has been carried out. The antioxidant activity has been determined by the method based on auto-oxidation of adrenaline; the antibacterial activity has been investigated by the method of double serial dilution with the use of Hottinger broth. The compounds investigated show only an insignificant antioxidant effect and the low activity towards the strains of such bacteria as E. coli, Ps. aeroginosa, B. subtilis and St. aureus. Compounds bearing diethoxyphosphonyl or methoxycarbonyl group at C-2 atom of a five- or six-member heterocycle show the similar activity in general. For 2-fluoroalkyl substituted 4-thiazolidinon- or 4-bezothiazinanones a considerable growth of the culture biomass has been revealed, and it can find application for growth stimulation of producers of biologically active compounds. Compounds incorporating the thiazinanones or bezothiazinanones fragment reveal the prooxidant effect, and it can become a basis for manifestation of the antineoplastic or antimicrobic activity.


Keywords


thiazolidinones; thiazinanones; benzothiazinanones; fluoroalkyl; aminophosphonates; aminocarboxylates; biological activity

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DOI: https://doi.org/10.24959/ophcj.14.814

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Abbreviated key title: Ž. org. farm. hìm.

ISSN 2518-1548 (Online), ISSN 2308-8303 (Print)