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Synthesis and preliminary biological screening of certain 5-aralkyl pyrrolidine-3-carboxylic acids as anticonvulsants

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Author(s): Mohamed Nabil Aboul-Enein | Aida Abd El-Sattar El-Azzouny | Ola Ahmed Saleh | Mahmoud Abd El-Moien Nawwar | Mohamed Abd El-Hamid Ismail | Mahmoud Gamal El-Din Elsedeek | Yousreya Aly Maklad

Journal: European Journal of Chemistry
ISSN 2153-2249

Volume: 1;
Issue: 2;
Start page: 102;
Date: 2010;
Original page

Keywords: Synthesis | 5-aralkyl pyrrolidine-3-carboxylic acids | Epilepsy | Anticonvulsants

ABSTRACT
Synthesis of a series of 5-aralkyl pyrrolidine-3-carboxylic acid derivatives namely, 1-acetyl-4-hydroxy-5-benzyl or 5-(4-alkoxy-benzyl)-pyrrolidine-3-carboxylic acids (3a-e), 1-H-4-hydroxy-5-benzyl or 5-(4-alkoxy-benzyl)-pyrrolidine-3-carboxylic acids (4a-e), 1-acetyl-5-benzyl or 5-(4-alkoxy-benzyl)-pyrrolidine-3-carboxylic acids (8a-e), 1-H-5-benzyl or 5-(4-alkoxy-benzyl)-pyrrolidine-3-carboxylic acids (9a-e) have been accomplished. The structures of the new compounds were assigned from IR, 1H NMR, 13C NMR and elemental analyses. Compounds 3a-e, 4a-e, 8a-e and 9a-e were biologically screened for their anticonvulsant potential using the subcutaneous pentylenetetrazole seizures (scPTZ) assay and Gabapentin as reference standard. The 1-H-4-hydroxy-5-benzyl or 5-(4-alkoxy-benzyl)-pyrrolidine-3-carboxylic acids (4a-e) showed the highest anticonvulsant activity. Compound 4b was found to be the most potent one which exhibited 100% protection.
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