Synthesis and biological evaluation of new 1,3-thiazolidine-4-one derivatives of 2-(4-isobutylphenyl)propionic acid.

New thiazolidine-4-one derivatives of 2-(4-isobutylphenyl)propionic acid (ibuprofen) have been synthesized as potential anti-inflammatory drugs. The structure of the new compounds was proved using spectral methods (FR-IR, 1H-NMR, 13C-NMR, MS). The in vitro antioxidant potential of the synthesized compounds was evaluated according to the total antioxidant activity, the DPPH and ABTS radical scavenging assays. Reactive oxygen species (ROS) and free radicals are considered to be involved in many pathological events like diabetes mellitus, neurodegenerative diseases, cancer, infections and more recently, in inflammation. It is known that overproduction of free radicals may initiate and amplify the inflammatory process via upregulation of genes involved in the production of proinflammatory cytokines and adhesion molecules. The chemical modulation of acyl hydrazones of ibuprofen 3a-l through cyclization to the corresponding thiazolidine-4-ones 4a-n led to increased antioxidant potential, as all thiazolidine-4-ones were more active than their parent acyl hydrazones and also ibuprofen. The most active compounds are the thiazolidine-4-ones 4e, m, which showed the highest DPPH radical scavenging ability, their activity being comparable with vitamin E.

Synthesis and biological evaluation of new 1,3-thiazolidine-4-one derivatives of nitro-l-arginine methyl ester.

BACKGROUND: l-Arginine is a semi-essential aminoacid with important role in regulation of physiological processes in humans. It serves as precursor for the synthesis of proteins and is also substrate for different enzymes such as nitric oxide synthase. This amino-acid act as free radical scavenger, inhibits the activity of pro-oxidant enzymes and thus acts as an antioxidant and has also bactericidal effect against a broad spectrum of bacteria. RESULTS: New thiazolidine-4-one derivatives of nitro-l-arginine methyl ester (NO2-Arg-OMe) have been synthesized and biologically evaluated in terms of antioxidant and antibacterial/antifungal activity. The structures of the synthesized compounds were confirmed by (1)H, (13)C NMR, Mass and IR spectral data. The antioxidant potential was investigated using in vitro methods based on ferric/phosphomolybdenum reducing antioxidant power and DPPH/ABTS radical scavenging assay. The antibacterial effect was investigated against Gram positive (Staphylococcus aureus ATCC 25923, Sarcina lutea ATCC 9341) and Gram negative (Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853) bacterial strains. The antifungal activity was also investigated against Candida spp. (Candida albicans ATCC 10231, Candida glabrata ATCC MYA 2950, Candida parapsilosis ATCC 22019). CONCLUSIONS: Synthesized compounds showed a good antioxidant activity in comparison with the NO2-Arg-OMe. The antimicrobial results support the selectivity of tested compounds especially on P. aeruginosa as bacterial strain and C. parapsilosis as fungal strain. The most proper compounds were 6g (R = 3-OCH3) and 6h (R = 2-OCH3) which showed a high free radical (DPPH, ABTS) scavenging ability and 6j (R = 2-NO2) that was the most active on both bacterial and fungal strains and also it showed the highest ABTS radical scavenging ability.Graphical abstract1: ethyl 3-aminopropionate hydrochloride, 2a-j: aromatic aldehydes, 3: thioglycolic acid, 4a-j: thiazolidine-propionic acid derivatives , 5: Nω-nitro-L-arginine methyl ester hydrochloride, 6a-j: thiazolidine-propionyl-nitro-L-arginine methyl ester derivatives.

New derivatives of aryl-propionic acid. Synthesis and biological evaluation.

AIM: To design new derivatives of aryl-propionic acid with potential antibacterial and antioxidant activity. MATERIAL AND METHODS: New hydrazone of ibuprofen (2-(4-isobutylphenyl)propionic acid) have been synthesized by reaction of ethyl ester of ibuprofen with hydrazine hydrate and then condensation of corresponding hydrazide with various aromatic aldehydes. RESULTS: The synthesized compounds were screened for their antibacterial activity against Gram positive (Staphylococcus aureus ATCC 25923, Sarcinalutea ATCC 9341, Bacillus cereus ATCC 14579, Bacillus subtilis) and Gram negative bacterial strains (Escherichia coli ATCC 25922). Some of them were found to have good antibacterial activity. The antioxidant activity of these compounds was also tested using the total antiox idant capacity test. CONCLUSIONS: The chemical modulations performed on ibuprofen structure have a good influence on the biological activity of the synthesized compounds.