European Journal of Chemistry

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



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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

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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References

[1]. Lindsay, J. M. Epilepsia 1971, 12, 47-54.
doi:10.1111/j.1528-1157.1971.tb03914.x
PMid:5282882

[2]. Blume, W.; Lüders, H.; Mizrahi, E.; Tassinari, C.; Boas, W. V. E.; Engle, J. Epilepsia 2001, 42, 1212-1218.
doi:10.1046/j.1528-1157.2001.22001.x
PMid:11580774

[3]. Fisher, R.; Boas, W. V. E.; Blume, W.; Elger, C.; Genton, P.; Lee, P.; Engel, J. Epilepsia 2005, 46, 470-472.
doi:10.1111/j.0013-9580.2005.66104.x
PMid:15816939

[4]. Engel, Jr. J.; Padley, T. A.; “Epilepsy a comprehensive text book” Lippincott-Raven, Philadelphia, 1998.

[5]. Baker, G. A.; Hargis, E.; Hsih, M. M.-S.; Mounfield, H.; Arzimanoglou, A.; Glauser, T.; Pellock, J.; Lund, S. Epilepsy and Behavior 2008, 12, 395-401.
PMid:18164251

[6]. Ismail, M. A. H.; Aboul-Enein, M. N.; Abouzid, K. A. M.; Abou El Ella, D. A.; Ismail, N. S. M. Bioorg. Med. Chem. 2009, 17, 3739-3746.
doi:10.1016/j.bmc.2009.03.008

[7]. Sircar, S. S. G. J. Chem. Soc. 1927, 1252-1256.

[8]. Long, M. J. Amer. Chem. Soc. 1951, 73, 4895-4898.
doi:10.1021/ja01154a126

[9]. Marshall, P. G.; Vallance, D. K. J. Pharm. Pharmacol. 1954, 6, 740-746.

[10]. Waser, V. P. G.; Ganz, A. J.; Pfirmann, R. W. Arzneim.-Forsch. 1977, 27, 1942-1953.
PMid:579105

[11]. Noyer, M.; Gillard, M.; Matagne, A. Eur. J. Pharmacol. 1995, 286, 137-146.
doi:10.1016/0014-2999(95)00436-O

[12]. Goodman; Y.; Mattson, M. P. J. Neurochem. 1996, 66, 869-72; Chem. Abst. 1996, 124, 165104d.

[13]. Labouta, I. M.; Jacobsen, P.; Thorbek, P.; Krogsgaard- Larsen, P.; Hjeds, H. Acta Chemica Scandinavica 1982, B 36, 669-74.

[14]. Rogawski, M. Br. J. Pharmacol. 2008, 154, 1555-1557.
doi:10.1038/bjp.2008.221
PMid:18552880    PMCid:2518467

[15]. Matagne, A.; Margineanu, D-G.; Potschka, H.; Loscher, W.; Michel, P.; Kenda, B.; Klitgaard, H. Eur. J. Pharmacol. 2009, 614, 30-37.
doi:10.1016/j.ejphar.2009.04.024
PMid:19383493

[16]. Aboul-Enein, M. N.; El-Azzouny, A. A.; Abdallah, N. A.; Maklad, Y. A.; Attia, M. I.; Ebeid, M. Y. Sci. pharm. 1997, 65, 225-245.

[17]. Aboul-Enein, M. N.; Ismail, M. A. H.; Maklad, Y. A.; Mohamed, N. S. Egypt. Pharm. J. 2003, 2, 94-121.

[18]. Aboul-Enein, M. N.; El-Azzouny, A. A.; Safwat, H. M.; Saleh, O. A.; Maklad, Y. A. Egypt. Pharm. J. 2005, 4, 549-578.

[19]. Balenovic, K.; Bregent, N. J. Org. Chem.1964, 19, 1589-1592.
doi:10.1021/jo01375a005

[20]. Satzinger, G.; Hartenstien, J.; Herrmann, M.; Heldt, W. U. S. Patent. 1977, 4,024, 175.

[21]. Keberel, H.; Faigle, J. W.; Wilhelm, M. U. S. Pat. 1969, 3,471, 548.

[22]. Aboul-Enein, M.N.; Khalifa, M.; El-Difrawy, S.M. Pharm. Acta Helv. 1973, 48, 405-411.

[23]. Aboul-Enein, M. N.; El-Difrawy, S. M.; Gadalla, K. Z.; Macklouf, A. A.; El Sayed, M. E. Egypt. J. Pharm. Sci. 1990, 31, 29-40.

[24]. Aboul-Enein, M. N.; El-Difrawy, S. M.; Nofal, Z. M.; El-Azzouny, A. A. Acta Pharm. Suec. 1982, 19, 309-316.
PMid:7136738

[25]. Pandeya, S. N.; Yogeeswari, P; Stables, J. P. Eur. J. Med.Chem. 2000, 35, 879-886. c) Parmar, S. S.; Gupta, A. K.; Gupta, T. K.; Stenberg, V. I. J. Pharm. Sci. 1975, 64, 154-157.

[26]. Hassert, G. L.; Poutsiaka, J.W.; Papandrianos, D.; Burke, J.C.; Carver, B.V. Toxicol. Appl. Pharmacol. 1961, 3, 726-741.
doi:10.1016/0041-008X(61)90036-9

[27]. Lado, F. A.; Sperber, E. F.; Moshe, S. L. Epilepsia 2001, 42, 458-463.
doi:10.1046/j.1528-1157.2001.30900.x
PMid:11440340

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National Research Centre, Dokki, Giza, Egypt
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