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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MDPI AG
2020-03-01
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| Series: | Scientia Pharmaceutica |
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| Online Access: | https://www.mdpi.com/2218-0532/88/1/16 |
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| author | Mariia Mishchenko Sergiy Shtrygol Danylo Kaminskyy Roman Lesyk |
| author_facet | Mariia Mishchenko Sergiy Shtrygol Danylo Kaminskyy Roman Lesyk |
| author_sort | Mariia Mishchenko |
| collection | DOAJ |
| description | 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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| issn | 2218-0532 |
| language | English |
| last_indexed | 2024-04-12T19:51:23Z |
| publishDate | 2020-03-01 |
| publisher | MDPI AG |
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| series | Scientia Pharmaceutica |
| spelling | doaj.art-b5c9947b9a8e4cfeb783517f7a0558672022-12-22T03:18:49ZengMDPI AGScientia Pharmaceutica2218-05322020-03-018811610.3390/scipharm88010016scipharm88010016Thiazole-Bearing 4-Thiazolidinones as New Anticonvulsant AgentsMariia Mishchenko0Sergiy Shtrygol1Danylo Kaminskyy2Roman Lesyk3Department of Pharmacology, National University of Pharmacy, Kulykovska 12, 61168 Kharkiv, UkraineDepartment of Pharmacology, National University of Pharmacy, Kulykovska 12, 61168 Kharkiv, UkraineDepartment of Pharmaceutical, Organic and Bioorganic Chemistry, Danylo Halytsky Lviv National Medical University, Pekarska 69, 79010 Lviv, UkraineDepartment of Pharmaceutical, Organic and Bioorganic Chemistry, Danylo Halytsky Lviv National Medical University, Pekarska 69, 79010 Lviv, UkraineHere, 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.https://www.mdpi.com/2218-0532/88/1/164-thiazolidinonesthiazolessynthesisanticonvulsant activity |
| spellingShingle | Mariia Mishchenko Sergiy Shtrygol Danylo Kaminskyy Roman Lesyk Thiazole-Bearing 4-Thiazolidinones as New Anticonvulsant Agents Scientia Pharmaceutica 4-thiazolidinones thiazoles synthesis anticonvulsant activity |
| title | Thiazole-Bearing 4-Thiazolidinones as New Anticonvulsant Agents |
| title_full | Thiazole-Bearing 4-Thiazolidinones as New Anticonvulsant Agents |
| title_fullStr | Thiazole-Bearing 4-Thiazolidinones as New Anticonvulsant Agents |
| title_full_unstemmed | Thiazole-Bearing 4-Thiazolidinones as New Anticonvulsant Agents |
| title_short | Thiazole-Bearing 4-Thiazolidinones as New Anticonvulsant Agents |
| title_sort | thiazole bearing 4 thiazolidinones as new anticonvulsant agents |
| topic | 4-thiazolidinones thiazoles synthesis anticonvulsant activity |
| url | https://www.mdpi.com/2218-0532/88/1/16 |
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