Synthesis of thiazolidin-4-ones and thiazinan-4-ones from 1-(2-aminoethyl)pyrrolidine as acetylcholinesterase inhibitors
| Autor: | Bruna Caetano Moreira, Mayara Sandrielly Pereira Soares, Taís Ferreira, Cinara Teiroba De Ávila, Gabriele A. Berwaldt, Luiza Spohr, Adriana M. das Neves, Roselia Maria Spanevello, Nathalia Stark Pedra, Wilson Cunico, Taís B. Goulart, Anita Avila de Souza |
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| Rok vydání: | 2019 |
| Předmět: |
Short Communication
pyrrolidine Thiazines RM1-950 Hippocampus 01 natural sciences Medicinal chemistry Pyrrolidine Structure-Activity Relationship chemistry.chemical_compound Drug Discovery Animals Rats Wistar Cerebral Cortex Pharmacology Dose-Response Relationship Drug Molecular Structure thiazolidin-4-ones 010405 organic chemistry astrocytes General Medicine Acetylcholinesterase Rats 0104 chemical sciences 010404 medicinal & biomolecular chemistry chemistry acetylcholinesterase inhibitors Thiazolidines thiazinan-4-ones Amine gas treating Cholinesterase Inhibitors Therapeutics. Pharmacology |
| Zdroj: | Journal of Enzyme Inhibition and Medicinal Chemistry, Vol 35, Iss 1, Pp 31-41 (2020) Journal of Enzyme Inhibition and Medicinal Chemistry |
| ISSN: | 1475-6374 1475-6366 |
| Popis: | The present study describes the synthesis of a novel series of thiazolidin-4-one and thiazinan-4-one using 1-(2-aminoethyl)pyrrolidine as amine precursor. All compounds were synthesised by one-pot three component cyclocondensation reaction from the amine, a substituted benzaldehyde and a mercaptocarboxylic acid. The compounds were obtained in moderate to good yields and were identified and characterised by 1H, 13 C, 2 D NMR and GC/MS techniques. The compounds also were screened for their in vitro acetylcholinesterase (AChE) activity in hippocampus and cerebral cortex on Wistar rats. The six most potent compounds have been investigated for their cytotoxicity by cell viability assay of astrocyte primary culture, an important cell of central nervous system. We highlighted two compounds (6a and 6k) that had the lowest IC50 in hippocampus (5.20 and 4.46 µM) and cerebral cortex (7.40 and 6.83 µM). These preliminary and important results could be considered a starting point for the development of new AChE inhibitory agents. |
| Databáze: | OpenAIRE |
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