Abstract
New thiazolidine-4-one derivatives based on the 4-aminophenazone (4-amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one) scaffold have been synthesized as potential anti-inflammatory drugs. The pyrazoline derivatives are known especially for their antipyretic, analgesic and anti-inflammatory effects, but recently there were synthesized new compounds with important antioxidant, antiproliferative, anticancer and antidiabetic activities. The beneficial effects of these compounds are explained by nonselective inhibition of cyclooxygenase izoenzymes, but also by their potential scavenging ability for reactive oxygen and nitrogen species. The structure of the new compounds was proved using spectroscopic methods (FR-IR, 1H-NMR, 13C-NMR, MS). The in vitro antioxidant potential of the synthesized compounds was evaluated according to the ferric reducing antioxidant power, phosphomolydenum reducing antioxidant power, DPPH and ABTS radical scavenging assays. The chemical modulation of 4-aminophenazone (6) through linkage to thiazolidine-propanoic acid derivatives 5a–l led to improved antioxidant potential, all derivatives 7a–l being more active than phenazone. The most active compounds are the derivatives 7e, and 7k, which showed the higher antioxidant effect depending on the antioxidant assay considered.
Highlights
The pyrazolin-5-one scaffold occupies an important place in the nonsteroidal anti-inflammatory drug (NSAID) class, having drawn considerable attention from researchers due to its interesting biological activities
We report the synthesis, structural characterization and antioxidant activity of some new thiazolidine-4-one derivatives that contain a pyrazoline-5-one moiety
In the 1H-NMR spectra of the pyrazoline-thiazolidine-4-one derivatives 7a–l, the amide bond proton resonates as single, doublet or multiplet between 9.67–8.96 ppm
Summary
The pyrazolin-5-one scaffold occupies an important place in the nonsteroidal anti-inflammatory drug (NSAID) class, having drawn considerable attention from researchers due to its interesting biological activities. Phenazone or antipyrine (2,3-dimethyl-1-phenyl-3-pyrazolin-5-one) is a well-known compound for its analgesic and antipyretic effecs, while its 4-amino derivative (4-amino-2,3-dimethyl-1-phenyl-3pyrazolin-5-one) has anti-inflammatory effects [11]. The biological effects of these compounds have been attributed to their scavenging ability against reactive species. Compounds with thiazolidine structures have been reported as anti-inflammatory and analgesic [18], antitubercular [19], antimicrobial and antifungal [20], antiviral (especially as anti-HIV agents [21]), anticancer, antioxidants [18], anticonvulsants [22] and antidiabetic agents [22,23]. We report the synthesis, structural characterization and antioxidant activity of some new thiazolidine-4-one derivatives that contain a pyrazoline-5-one moiety
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