Abstract
A series of N-benzylidenepyridin-4-amines (1a–1j) were synthesized by refluxing 4-aminopyridine with various substituted aromatic aldehydes in toluene. The structures of the synthesized compounds were confirmed on the basis of IR, 1H NMR, 13C NMR, and mass spectroscopy data. The synthesized compounds were screened for anthelmintic activity on earth worms. Tested compounds showed paralysis time from 0.44 to 2.46 min and death time from 1.03 to 3.50 min, whereas the standard drugs albendazole and piperazine citrate showed paralysis time of 0.54 and 0.58 min and death time of 2.16 and 2.47 min, respectively, at the same concentration of 1 % m/V. Three compounds, including N-(2-hydroxybenzylidene)pyridin-4-amine (1e), N-(4-nitrobenzylidene)pyridin-4-amine (1h), and N-(4-methoxybenzylidene)pyridin-4-amine (1j), showed significant anthelmintic activity compared to the standard drugs.
Similar content being viewed by others
References
M. I. Ayad, A. Sh. Sallam, and H. E. Mabrouk, Thermochim. Acta, 189, 65–73 (1991); DOI: 10.1016/0040-6031(91)87100-B.
H. Temel, U. Cakir and H. I. Ugras, Russ. J. Inorg. Chem., 46, 1846–1850 (2001).
D. K. Johnson, T. B. Murphy, N. J. Rose, et al., Inorg. Chim. Acta, 67, 159–165 (1982); DOI: 10.1016/S0020-1693(00)85058-6.
L. T. Yildirim, K. C. Emregul, R. Kurtaran, et al., Cryst. Res. Technol., 37, 1344–1351 (2002); DOI: 10.1002/crat.200290012.
Y. Hao and H. Shen, Spectrochim. Acta A, 56, 1013–1020 (2000); DOI: 10.1016/S1386-1425(99)00286-3.
P. B. Miniyar and S. J. Makhija, Int. J. Drug Dev. Res., 1, 19–26 (2009).
H. Bulut, M. Karatepe, H. Temel, et al., Asian J. Chem., 17, 2793–2796 (2005).
A. Cukurovali, I. Yilmaz, S. Gur, et al., Eur. J. Med. Chem., 41, 201–207 (2006); DOI: 10.1016/j.ejmech.2005.01.013.
E. Ispir, Dyes Pigments, 82, 13–19 (2009); DOI: 10.1016/j.dyepig.2008.09.019.
E. Tsuchida and K. Oyaizu, Coord. Chem. Rev., 237, 213–228 (2003); DOI: 10.1016/S0010-8545(02)00251-5.
E. Kwiatkowski, G. Romanowski, W. Nowicki, et al., Polyhedron, 22, 1009–1018 (2003); DOI: 10.1016/S0277-5387(03)00041-X.
G.-M. Chen and H. C. Brown, J. Am. Chem. Soc., 122, 4217–4218 (2000); DOI: 10.1021/ja993965v.
A. Sidhu and M. Rai, Indian J. Chem., 47B, 778–780 (2008).
H. S. Hothi, A. Makkar, J. R. Sharma, et al., Eur. J. Med. Chem., 41, 253–255 (2006); DOI: 10.1016/j.ejmech.2005.07.016.
R. K. Sandhar, J. R. Sharma, and M. R. Manrao, J. Indian Chem. Soc., 85, 220–223 (2008).
M. Rai, V. Khera, V. K. Kaul, et al., J. Indian Chem. Soc., 83, 208–209 (2006).
N. Rani, J. R. Sharma, V. K. Kaul, et al., J. Indian Chem. Soc., 85, 1041–1044 (2008).
M. M. Hania, E-J. Chem., 6, 629–632 (2009); DOI: 10.1155/2009/104058.
I. J. Kuppast and P. V. Nayak, Indian J. Nat. Prod., 19, 27–29 (2003).
Acknowledgments
The author is grateful to IIMT College of Medical Sciences (Meerut) for providing research facilities to pursue this work.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Dutta, S. Synthesis and Anthelmintic Activity of N-Benzylidenepyridin-4-amines. Pharm Chem J 48, 448–451 (2014). https://doi.org/10.1007/s11094-014-1129-0
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11094-014-1129-0