SYNTHESIS AND STUDY OF ANTI-INFLAMMATORY ACTIVITY OF SOME THIAZOLO[4,3-b]QUINAZOLINES
DOI:
https://doi.org/10.11603/2312-0967.2020.4.11656Keywords:
intramolecular cyclization, thiazolo[4,3-b]quinazolines, Knoevenagel condensation, azo coupling, anti-inflammatory activityAbstract
The aim of work. To carry out the synthesis of some thiazolo[4,3-b]quinazolines, and to study the anti-inflammatory activity of the newly synthesized compounds.
Materials and methods. Methods of organic synthesis, NMR spectroscopy, elemental analysis, pharmacological screening.
Results and Discussion. In order to obtain new biologically active substances, we have proposed a method for the formation of a hard-to-reach thiazolo[4,3-b]quinazoline system based on the intramolecular cyclization of 2-(2-oxo-thiazolidin-4-ylideneamino) -benzoic acid. Based on the reactions of Knoevenagel condensation and azo coupling, the functionalization of the C3 position of the base 3H-thiazolo[4,3-b]quinazoline-1,9-dione was carried out with the formation of the corresponding 3-arylidene and 3-arylhydrazo derivatives. The structure of the obtained compounds and the interpretation of the performed chemical studies were confirmed by the data of elemental analysis and 1H NMR spectroscopy. Pharmacological screening for anti-inflammatory activity was performed. The results obtained made it possible to isolate 2 compounds with a pronounced anti-inflammatory effect, which in terms of activity are close to or exceed the reference drug Ibuprofen, which suggests that this condensed system is a promising molecular framework for the design of potential anti-inflammatory agents.
Conclusions. It was found that when using dehydrating agents, 2- (2-oxothiazolidin-4-ylideneamino) -benzoic acid undergoes cyclization to form the 3H-thiazolo[4,3-b]quinazoline-1,9-dione. The resulting scaffold reacted in Knoevenagel condensation and azo coupling reactions to obtain the corresponding C3 substituted thiazolo[4,3-b]quinazolines. In the process of studying anti-inflammatory activity, 2 highly active compounds were isolated.
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