Convenient Synthesis and Biological Activity of 4-minomethylene 1-phenylpyrazolidine-3,5-diones

Authors

  • Eman A. Ahmed Faculty of Science, Sohag University, 82524 Sohag, Egypt

DOI:

https://doi.org/10.29356/jmcs.v59i3.33

Keywords:

pyrazolidine-3, 5-diones, enaminones, nucleophiles, anti- inflammatory activity, antimicrobial activity.

Abstract

Reaction of (Z)-4-((dimethylamino)methylene)-1-phenylpyrazolidine-3,5-dione (1) with different nucleophiles is described. Treatment of enaminone 1 with phenylhydrazine led to 3-oxo-N’,2-diphenyl-2,3-dihydro-1H-pyrazole-4-carbohydrazide 7. New enaminone derivatives 2–6 and 12–14 were conveniently obtained in high yields via nucleophilic substitution of the dimethylamino group in enaminone 1 when reacted with o-aminophenol, o-aminothiophenol, ethanolamine, cysteamine hydrochloride, piperidine, morpholine, 2-aminopyridine and glycine. Reaction of enaminone 1 with diaza-nucleophiles, such as hydrazine hydrate, ethylenediamine and o-phenylenediamine, afforded the corresponding bis-enaminones 9–11. Anti-inflammatory and antimicrobial activities of some new products were evaluated. Compounds 1, 2, 4, 7, 12a, and 12b showed high anti- inflammatory activity compared with indomethacin as the reference, while the highest antimicrobial effect was observed in the case of compound 3.

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Author Biography

Eman A. Ahmed, Faculty of Science, Sohag University, 82524 Sohag, Egypt

Chemistry Department, Faculty of Science

References

Singh, K.; Singh, J.; Singh, H. Tetrahedron 1998, 54, 935–942.

Shawali, A. S.; Haboub, A. J. M. J. Chem. Res. 2011, 35, 341–345.

Al-Awadi, N. A.; Ibrahim, M. R.; Elnagdi, M. H.; John, E.; Ibrahim, Y. A. Beilstein J. Org. Chem. 2012, 8, 441–447.

Dominguez, E.; Ibeas, E.; de Maigorta, E. M.; Palacios, J. K.; SanMartin, R. A. J. Org. Chem. 1996, 61, 5435–5439.

Nikolovaa, S.; Kochovskaa, E.; Ivanov, I. Synth. Commun. 2013, 43, 326-336.

Khodairy, A. Synth. Commun. 2011, 41, 612-621.

Nagaraju, V.; Purnachander, D.; Rao Mangina, N. S. V. M.; Suresh, S.; Sridhar, B.; Karunakar, G. V. Org. Biomol. Chem. 2015, 13, 3011-3023.

Khurana, M.; Salama, N. N.; Scott, K. R., Nemieboka, N. N.; Bauer, K. S. Jr.; Eddington, N. D. Biopharm. Drug Dispos. 2003, 24, 397–407.

Thumar, N. J.; Patel, M. P. Saudi Pharm J. 2011, 19, 75–83.

Michael, J. P.; Koning, C. B.; Hosken, G. D.; Stanbury, T. V. Tetrahedron 2001, 57, 9635–9648.

Jackson, P. L.; Hanson, C. D.; Farrell, A. K.; Butcher, R. J.; Stables, J. P.; Eddington, N. D.; Scott, R. K. Eur. J. Med. Chem. 2012, 5, 42–51.

Riyadh, S. M. Molecules 2011, 16, 1834-1853.

El-Shennawy, A. M.; Mohamed, A. H.; Abass, M. Medscape Gen. Med. J. 2007, 9, 15–33.

Naringrekar, V. H.; Stella, V. J. J. Pharm. Sci. 1990, 79, 138–146.

El-Deeb, I. M.; Lee, S. H. Bioorg. Med. Chem. 2010, 18, 3961–3973.

Rashad, A. E.; Hegab, M. I.; Abdel-Megeid, R. E.; Micky, J. A.; Abdel-Megeid, F. M. E. Bioorg. Med. Chem. 2008, 16, 7102–7106.

El-Hashim, A.; Yousefi, S.; Edafiogho, I.; Raghupathy, R.; Yousif, M.; Simon, H. Eur. J. Pharm. 2010, 632, 73–78.

Kolle, U.; Kolb, B.; Mannschreck, A. Chem. Ber. 1980, 113, 2545-2565.

Crystallographic data have been deposited at the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 964084. Akkurt, M.; Mohamed, S. K.; Elremaily, M. A. A.; Ahmed, E. A.; Albayati, M. R. Acta Crystallogr. E 2013, 69, o1408–o1409.

Crystallographic data have been deposited at the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 1005600. Mague, J. T.; Mohamed, S. K.; Akkurt, M.; Ahmed, E. A.; Albayati, M. R. Acta Crystallogr. E 2014, 70, o819–o820.

Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270–283.

Janoschek, R. Pure Appl. Chem. 2001, 73, 1521-1553.

Crystallographic data have been deposited at the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 1015152. Mohamed, S. K.; Akkurt, M.; Mague, J. T.; Ahmed, E. A. and Albayati, M. R. Acta Crystallogr. E 2014, 70, o938–o939.

Kataoka, T.; Teraoka, J.; Sakoda, A.; Nishiyama, Y.; Yamato, K.; Monden, M., Ishimori, Y.; Nomura, T.; Taguc, T., Yamaoka, K. Inflammation 2012, 35, 713–722.

Winter, C. A.; Risley, E. A.; Nuss, G. W. Experiment. Biol. Med. 1962, 111, 544–547.

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Published

2017-10-12

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Regular Articles