Abstract
The synthesis, anti-inflammatory and antioxidant properties of novel 5-hydroxy-7-methyl-3H-thiazolo[4,5-b]pyridin-2-one derivatives were discussed. Fused thiazolo[4,5-b]pyridin-2-ones were synthesized and modified at the N3, C5 and C6 positions of the main core in order to obtain the compounds with a satisfactory pharmacological profile. The synthesized compounds were preselected via molecular docking for further testing of their anti-inflammatory activity in vitro. Evaluation of novel compounds over the carageenin induced rat paw edema revealed strong anti-inflammatory action of some compounds including (thiazolo[4,5-b]pyridin-3(2H)-yl) propanenitrile (5) and thiazolo[4,5-b]pyridin-3(2H)-yl) propanoic acid (6) even exceeding the standard - Ibuprofen. The antioxidant activity of the synthesized compounds was measured in vitro by the method of scavenging effect on 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals.
Highlights
Literature data survey has revealed that numerous nonsteroidal anti-inflammatory drugs (NSAIDs), which belong to different chemical classes, have been developed to treat inflammatory disorders
The present work is devoted to the synthesis of a series of novel 3H-thiazolo[4,5-b]pyridine-2-ones by the structural modification of the core heterocycle in its N3, C5 and C6 positions for further pharmacological in vivo anti-inflammatory activity assay based on the results obtained via computer simulation – molecular docking and in vitro antioxidant screenings
We looked at a possibility to use the reported method for preparation of 3-phenyl-5-hydroxy-7-methyl-3Hthiazolo[4,5-b]pyridin-2-one [4] from above mentioned ethyl acetoacetate and 3-phenyl-4-iminothiazolidone2-onе
Summary
Inflammation is an essential response of living organisms to the common ailments starting from traumatic disorder or fever associated with infection to major life-threatening diseases like myocardial infarction or brain haemorrhage or infarct. Literature data survey has revealed that numerous nonsteroidal anti-inflammatory drugs (NSAIDs), which belong to different chemical classes, have been developed to treat inflammatory disorders. Inhibition of COX-1 is responsible, in part, for gastrointestinal side effects, which are the most frequent side effects of NSAIDs.4 These conditions generate one of the biggest challenges of modern medicinal chemistry for the development of alternative anti-inflammatory drugs with minimal adverse effects.. In summing up the published scientific data fused thiazolopyridines are characterized by herbicidal, antioxidant, antimicrobial, antifungal, and anti-mitotic activities. They show potent inhibitory activities for Aβ42 fibrillization for Alzheimer’s disease treatment.. Exploration of different chemical modifications avenues of thiazolopyridines to obtain novel active compounds, and the development of a new class of anti-inflammatory drugs with optimal pharmacokinetic properties should be continued. The present work is devoted to the synthesis of a series of novel 3H-thiazolo[4,5-b]pyridine-2-ones by the structural modification of the core heterocycle in its N3, C5 and C6 positions for further pharmacological in vivo anti-inflammatory activity assay based on the results obtained via computer simulation – molecular docking and in vitro antioxidant screenings
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