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Synthesis of 3-Arylidene-4-Piperidone Derivatives as Potent Antioxidant Agents: A Solvent Free Approach
Corresponding Author(s) : P. Venkatesan
Asian Journal of Chemistry,
Vol. 31 No. 2 (2019): Vol. 31 No. 2
Abstract
A simple procedure using grinding method of condensation of N-acetyl-3-methyl-2,6-diarylpiperidin-4-one with aldehyde gave N-acetyl-3-arylidene-5-methyl-2,6-diarylpiperidin-4-one with good yield. The structure of the synthesized compounds was assigned on the basis of IR, 1H NMR and mass spectral studies. The synthesized compounds showed remarkable in vitro antioxidant activity.
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- M.A. Pasha and B. Datta, J. Saudi Chem. Soc., 18, 47 (2014); https://doi.org/10.1016/j.jscs.2011.05.012.
- A.L. Garay, A. Pichon and S.L. James, Chem. Soc. Rev., 36, 846 (2007); https://doi.org/10.1039/b600363j.
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- B.R. Madje, S.S. Shindalkar, M.N. Ware and M.S. Shingare, ARKIVOC, 82 (2005); https://doi.org/10.3998/ark.5550190.0006.e10.
- Z.-B. Xie, N. Wang, M.-Y. Wu, T. He, Z.-G. Le and X.-Q. Yu, Beilstein J. Org. Chem., 8, 534 (2012); https://doi.org/10.3762/bjoc.8.61.
- J.M. Harrowfield, R.J. Hart and R. Whitaker, Aust. J. Chem., 54, 423 (2001); https://doi.org/10.1071/CH01166.
- M. Phukan, M.K. Kalita and R. Borah , Green Chem. Lett. Rev., 3, 329 (2010); https://doi.org/10.1080/17518253.2010.487841.
- P. Tripathi, A.C. Tripathi, V. Chawla and S.K. Saraf, Eur. J. Med. Chem., 82, 439 (2014); https://doi.org/10.1016/j.ejmech.2014.05.080.
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- P. Venkatesan and T. Maruthavanan, Nat. Prod. Res., 29, 2092 (2015); https://doi.org/10.1080/14786419.2015.1009456.
- H.N. Pati, U. Das, S. Das, B. Bandy, E. De Clercq, J. Balzarini, M. Kawase, H. Sakagami, J.W. Quail, J.P. Stables and J.R. Dimmock, Eur. J. Med. Chem., 44, 54 (2009); https://doi.org/10.1016/j.ejmech.2008.03.015.
- T. Kalai, M.L. Kuppusamy, M. Balog, K. Selvendiran, B.K. Rivera, P. Kuppusamy and K. Hideg, J. Med. Chem., 54, 5414 (2011); https://doi.org/10.1021/jm200353f.
- C.R. Noller and V. Baliah, J. Am. Chem. Soc., 70, 3853 (1948); https://doi.org/10.1021/ja01191a092.
- A. Manimekalai, K. Selvaraju and T. Maruthavanan, Indian J. Chem., 46B, 160 (2007).
- M. Biswas, P.K. Haldar and A.K. Ghosh, J. Nat. Sci. Biol. Med., 1, 29 (2010); https://doi.org/10.4103/0976-9668.71670.
References
M.A. Pasha and B. Datta, J. Saudi Chem. Soc., 18, 47 (2014); https://doi.org/10.1016/j.jscs.2011.05.012.
A.L. Garay, A. Pichon and S.L. James, Chem. Soc. Rev., 36, 846 (2007); https://doi.org/10.1039/b600363j.
R.A. Sheldon, Green Chem., 7, 267 (2005); https://doi.org/10.1039/b418069k.
A. Orita, L. Jiang, T. Nakano, N. Ma and J. Otera, Chem. Commun., 13, 1362 (2002); https://doi.org/10.1039/b203651g.
B.R. Madje, S.S. Shindalkar, M.N. Ware and M.S. Shingare, ARKIVOC, 82 (2005); https://doi.org/10.3998/ark.5550190.0006.e10.
Z.-B. Xie, N. Wang, M.-Y. Wu, T. He, Z.-G. Le and X.-Q. Yu, Beilstein J. Org. Chem., 8, 534 (2012); https://doi.org/10.3762/bjoc.8.61.
J.M. Harrowfield, R.J. Hart and R. Whitaker, Aust. J. Chem., 54, 423 (2001); https://doi.org/10.1071/CH01166.
M. Phukan, M.K. Kalita and R. Borah , Green Chem. Lett. Rev., 3, 329 (2010); https://doi.org/10.1080/17518253.2010.487841.
P. Tripathi, A.C. Tripathi, V. Chawla and S.K. Saraf, Eur. J. Med. Chem., 82, 439 (2014); https://doi.org/10.1016/j.ejmech.2014.05.080.
S.T. Harini, H.V. Kumar, J. Rangaswamy and N. Naik, Bioorg. Med. Chem. Lett., 22, 7588 (2012); https://doi.org/10.1016/j.bmcl.2012.10.019.
P. Venkatesan and T. Maruthavanan, Nat. Prod. Res., 29, 2092 (2015); https://doi.org/10.1080/14786419.2015.1009456.
H.N. Pati, U. Das, S. Das, B. Bandy, E. De Clercq, J. Balzarini, M. Kawase, H. Sakagami, J.W. Quail, J.P. Stables and J.R. Dimmock, Eur. J. Med. Chem., 44, 54 (2009); https://doi.org/10.1016/j.ejmech.2008.03.015.
T. Kalai, M.L. Kuppusamy, M. Balog, K. Selvendiran, B.K. Rivera, P. Kuppusamy and K. Hideg, J. Med. Chem., 54, 5414 (2011); https://doi.org/10.1021/jm200353f.
C.R. Noller and V. Baliah, J. Am. Chem. Soc., 70, 3853 (1948); https://doi.org/10.1021/ja01191a092.
A. Manimekalai, K. Selvaraju and T. Maruthavanan, Indian J. Chem., 46B, 160 (2007).
M. Biswas, P.K. Haldar and A.K. Ghosh, J. Nat. Sci. Biol. Med., 1, 29 (2010); https://doi.org/10.4103/0976-9668.71670.