Synthesis, Molecular Docking and Biological Properties of Novel Thiazolo[4,5-b]pyridine derivatives

• Main Authors: Taras I. Chaban, Julia E. Matiychuk, Olga Ya. Shyyka, Ihor G. Chaban, Volodymyr V. Ogurtsov, Ihor A. Nektegayev, Vasyl S. Matiychuk
• Format: Article
• Language: English
• Published: Slovenian Chemical Society 2020-12-01
• Series: Acta Chimica Slovenica
• Subjects: organic synthesis; thiazolo[4,5-b]pyridin-2-ones; anti-inflammatory activity; antioxidant activity; molecular docking
• Online Access: https://journals.matheo.si/index.php/ACSi/article/view/5439

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.