European Journal of Chemistry

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

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Published: Jun 15, 2010
DOI: https://doi.org/10.5155/eurjchem.1.2.102-109.47
Keywords:
Synthesis, 5-aralkyl pyrrolidine-3-carboxylic acids, Epilepsy, Anticonvulsants
Section
Research Article
Issue
Vol. 1 No. 2 (2010): June 2010
Dates
Received 2010-04-08
Accepted 2010-05-07
Published 2010-06-15


Main Article Content

Mohamed Nabil Aboul-Enein
Medicinal and Pharmaceutical Chemistry Department, Pharmaceutical and Drug Industries Research Division, National Research Centre, Dokki-Giza, 12622, Egypt
Aida Abd El-Sattar El-Azzouny
Medicinal and Pharmaceutical Chemistry Department, Pharmaceutical and Drug Industries Research Division, National Research Centre, Dokki-Giza, 12622, Egypt
Ola Ahmed Saleh
Medicinal and Pharmaceutical Chemistry Department, Pharmaceutical and Drug Industries Research Division, National Research Centre, Dokki-Giza, 12622, Egypt
Mahmoud Abd El-Moien Nawwar
Phytochemistry and Chemosystematic Department, Pharmaceutical and Drug Industries Research Division, National Research Centre, Dokki-Giza, 12622, Egypt
Mohamed Abd El-Hamid Ismail
Pharmaceutical Chemistry Department, Faculty of Pharmacy, Ain Shams University, Cairo, 11566, Egypt
Mahmoud Gamal El-Din Elsedeek
Medicinal and Pharmaceutical Chemistry Department, Pharmaceutical and Drug Industries Research Division, National Research Centre, Dokki-Giza, 12622, Egypt
Yousreya Aly Maklad
Medicinal and Pharmaceutical Chemistry Department, Pharmaceutical and Drug Industries Research Division, National Research Centre, Dokki-Giza, 12622, Egypt

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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Aboul-Enein, M. N.; El-Azzouny, A. A. E.-S.; Saleh, O. A.; Nawwar, M. A. E.-M.; Ismail, M. A. E.-H.; Elsedeek, M. G. E.-D.; Maklad, Y. A. Synthesis and Preliminary Biological Screening of Certain 5-Aralkyl Pyrrolidine-3-Carboxylic Acids As Anticonvulsants. Eur. J. Chem. 2010, 1, 102-109.

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National Research Centre, Dokki, Giza, Egypt
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