Thiazole-Bearing 4-Thiazolidinones as New Anticonvulsant Agents
Here, we describe the synthesis and anticonvulsant activity of thiazole-bearing hybrids based on 2-imino-4-thiazolidinone and 2,4-dioxothiazolidine-5-carboxylic acid cores. The structure of target compounds was based on the following: (<i>i</i>) A combination of two thiazole cores; (<...
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| Main Authors: | , , , |
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| Format: | Book |
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MDPI AG,
2020-03-01T00:00:00Z.
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| Summary: | Here, we describe the synthesis and anticonvulsant activity of thiazole-bearing hybrids based on 2-imino-4-thiazolidinone and 2,4-dioxothiazolidine-5-carboxylic acid cores. The structure of target compounds was based on the following: (<i>i</i>) A combination of two thiazole cores; (<i>ii</i>) similarity to ralitolin’s structure; (<i>iii</i>) the compliance with structural requirements for the new anticonvulsants. Target compounds were synthesized via known approaches based on Knoenavegel reaction, alkylation reaction, and one-pot three-component reaction. Anticonvulsant properties of compounds were evaluated in two different models—pentylenetetrazole-induced seizures and maximal electroshock seizure tests. Among the tested compounds 5<i>Z</i>-(3-nitrobenzylidene)-2-(thiazol-2-ylimino)-thiazolidin-4-one <b>Ib</b>, 2-[2,4-dioxo-5-(thiazol-2- ylcarbamoylmethyl)-thiazolidin-3-yl]-<i>N</i>-(2-trifluoromethylphenyl)acetamide <b>IId</b> and (2,4-dioxo-5- (thiazol-2-ylcarbamoylmethylene)-thiazolidin-3-yl)acetic acid ethyl ester <b>IIj</b> showed excellent anticonvulsant activity in both models. The directions of compounds modification based on SAR aspects were discussed. The results of the study provide a basis for further study of the anticonvulsant properties of selected thiazole-thiazolidinones. |
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| Item Description: | 2218-0532 10.3390/scipharm88010016 |