European Journal of Chemistry 2010, 1(2), 102-109 | doi: https://doi.org/10.5155/eurjchem.1.2.102-109.47 | Get rights and content

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


Mohamed Nabil Aboul-Enein (1,*) , Aida Abd El-Sattar El-Azzouny (2) , Ola Ahmed Saleh (3) , Mahmoud Abd El-Moien Nawwar (4) , Mohamed Abd El-Hamid Ismail (5) , Mahmoud Gamal El-Din Elsedeek (6) , Yousreya Aly Maklad (7)

(1) Medicinal and Pharmaceutical Chemistry Department, Pharmaceutical and Drug Industries Research Division, National Research Centre, Dokki-Giza, 12622, Egypt
(2) Medicinal and Pharmaceutical Chemistry Department, Pharmaceutical and Drug Industries Research Division, National Research Centre, Dokki-Giza, 12622, Egypt
(3) Medicinal and Pharmaceutical Chemistry Department, Pharmaceutical and Drug Industries Research Division, National Research Centre, Dokki-Giza, 12622, Egypt
(4) Phytochemistry and Chemosystematic Department, Pharmaceutical and Drug Industries Research Division, National Research Centre, Dokki-Giza, 12622, Egypt
(5) Pharmaceutical Chemistry Department, Faculty of Pharmacy, Ain Shams University, Cairo, 11566, Egypt
(6) Medicinal and Pharmaceutical Chemistry Department, Pharmaceutical and Drug Industries Research Division, National Research Centre, Dokki-Giza, 12622, Egypt
(7) Medicinal and Pharmaceutical Chemistry Department, Pharmaceutical and Drug Industries Research Division, National Research Centre, Dokki-Giza, 12622, Egypt
(*) Corresponding Author

Received: 08 Apr 2010 | Accepted: 07 May 2010 | Published: 15 Jun 2010 | Issue Date: June 2010

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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Keywords


Synthesis; 5-aralkyl pyrrolidine-3-carboxylic acids; Epilepsy; Anticonvulsants

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DOI: 10.5155/eurjchem.1.2.102-109.47

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Funding information


National Research Centre, Dokki, Giza, Egypt

Citations

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[1]. Walaa Hamada Abd-Allah, Mona Elsayed Aboutabl, Mohamed Nabil Aboul-Enein, Aida Abdel Sattar El-Azzouny
Synthesis, molecular modeling studies and anticonvulsant activity of certain (1-(benzyl (aryl) amino) cyclohexyl) methyl esters
Bioorganic Chemistry  71, 135, 2017
DOI: 10.1016/j.bioorg.2017.01.021
/


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How to cite


Aboul-Enein, M.; El-Azzouny, A.; Saleh, O.; Nawwar, M.; Ismail, M.; Elsedeek, M.; Maklad, Y. Eur. J. Chem. 2010, 1(2), 102-109. doi:10.5155/eurjchem.1.2.102-109.47
Aboul-Enein, M.; El-Azzouny, A.; Saleh, O.; Nawwar, M.; Ismail, M.; Elsedeek, M.; Maklad, Y. Synthesis and preliminary biological screening of certain 5-aralkyl pyrrolidine-3-carboxylic acids as anticonvulsants. Eur. J. Chem. 2010, 1(2), 102-109. doi:10.5155/eurjchem.1.2.102-109.47
Aboul-Enein, M., El-Azzouny, A., Saleh, O., Nawwar, M., Ismail, M., Elsedeek, M., & Maklad, Y. (2010). Synthesis and preliminary biological screening of certain 5-aralkyl pyrrolidine-3-carboxylic acids as anticonvulsants. European Journal of Chemistry, 1(2), 102-109. doi:10.5155/eurjchem.1.2.102-109.47
Aboul-Enein, Mohamed, 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. "Synthesis and preliminary biological screening of certain 5-aralkyl pyrrolidine-3-carboxylic acids as anticonvulsants." European Journal of Chemistry [Online], 1.2 (2010): 102-109. Web. 10 May. 2021
Aboul-Enein, Mohamed, El-Azzouny, Aida, Saleh, Ola, Nawwar, Mahmoud, Ismail, Mohamed, Elsedeek, Mahmoud, AND Maklad, Yousreya. "Synthesis and preliminary biological screening of certain 5-aralkyl pyrrolidine-3-carboxylic acids as anticonvulsants" European Journal of Chemistry [Online], Volume 1 Number 2 (15 June 2010)

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