Abstract
A catalyst-free greener protocol for the most effective one-pot synthesis of 2,6-diamino-4-aryl-1-propyl/cyclohexyl-1,4-dihydropyridine-3,5-dicarbonitrile derivatives has been developed using a simple three-component reaction of structurally diverse aldehydes, malononitrile and n-propylamine/cyclohexylamine at an ambient temperature. The formation of 1,4-dihydropyridines could be achieved in aqueous methanol in a single synthetic process involving no chromatography. The newly synthesized highly functionalized 1,4-DHPs have been screened for their in vitro antioxidant activity using the DPPH radical scavenging technique and the results were good in comparison with a standard drug.
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References
A. Chanda, V.V. Fokin, Chem. Rev. 109, 725 (2009)
A. Domling, I. Ugi, Angew. Chem. Int. Ed. 39, 3168 (2000)
B. Adrom, N. Hazeri, M.T. Maghsoodlou, M. Mollamohammadi, Res. Chem. Intermed. (2014). doi:10.1007/s11164-014-1564-2
N.G. Khaligh, T. Mihankhah, Res. Chem. Intermed. (2014). doi:10.1007/s11164-014-1552-6
B.B. Fredholm, A.P. Ijzerman, K.A. Jacobon, K.N. Klotz, J. Linden, Pharmacol. Rev. 53, 527 (2001)
V. Perrier, A.C. Wallace, K. Kaneko, J. Safar, S.B. Prusiner, F.E. Cohen, Proc. Natl. Acad. Sci. USA 97, 6073 (2000)
F. Zhang, Y. Zhao, L. Sun, L. Ding, Y. Gu, P. Gong, Eur. J. Med. Chem. 46, 3149 (2011)
A.A. Bekhit, A.M. Baraka, Eur. J. Med. Chem. 40, 1405 (2005)
T. Murata, M. Shimada, S. Sakakibara, T. Yoshino, H. Kadono, T. Masuda, M. Shimazaki, T. Shintani, K. Fuchikami, K. Sakai, H. Inbe, K. Takeshita, T. Niki, M. Umeda, K.B. Bacon, K.B. Ziegelbauer, T.B. Lowinger, Bioorg. Med. Chem. Lett. 13, 913 (2003)
M. Mantri, O. De Graaf, J.V. Veldhoven, A. Goblyos, V.F.D. Kunzel, T.M. Krieger, R. Link, H. De Vries, M.W. Beukers, J. Brussee, A.P. Ijzerman, J. Med. Chem. 51, 4449 (2008)
J. Deng, T. Sanchez, L.Q. Al-Mawsawi, R. Dayam, R.A. Yunes, A. Garofalo, M.B. Bolger, N. Neamati, Bioorg. Med. Chem. 15, 4985 (2007)
D. Kumar, V.B. Reddy, S. Sharad, U. Dube, S.A. Kapur, Eur. J. Med. Chem. 44, 3805 (2009)
Y.M. Litvinov, A.M. Shestopalov, In Advances in Heterocyclic Chemistry; A.R. Katritzky, Ed.; Academic Press: New York, 103, 175 (2011)
B. Love, K.M. Snader, J. Org. Chem. 30, 1914 (1965)
R. Alajarin, J.J. Vaquero, J.L.N. Garcia, J.A. Builla, Synlett, 1992, 297 (1992)
A. Sausins, G. Duburs, Heterocycles 27, 269 (1988)
M. Abaszadeh, M. Seifi, A. Asadipour, Res. Chem. Intermed. (2014). doi:10.1007/s11164-014-1624-7
N.M. Evdokimov, I.V. Magedov, A.S. Kireev, A. Kornienko, Org. Lett. 8, 899 (2006)
J. Sun, Y. Sun, Y. Xia, C.G. Yan, ACS Comb. Sci. 13, 436 (2011)
W. Zhang, X. Yang, W. Chen, X. Xu, L. Li, H. Zhai, Z. Li, J. Agric. Food Chem. 58, 2741 (2010)
M. Li, Z. Zuo, L. Wen, S. Wang, J. Comb. Chem. 10, 436 (2008)
S.S. Mansoor, K. Aswin, K. Logaiya, P.N. Sudhan, S. Malik, Res. Chem. Intermed. 40, 871 (2014)
K. Aswin, S.S. Mansoor, K. Logaiya, S.P.N. Sudhan, V.S. Malik, H. Ramadoss, Res. Chem. Intermed. 40, 2583 (2014)
J.M.C. Gutteridge, Free Radic. Res. Comm. 19, 141 (1995)
M.S. Blois, Nature 181, 1199 (1958)
D. Rajguru, B.S. Keshwal, S. Jain, Med. Chem. Res. 22, 5934 (2013)
Acknowledgments
R.R. gratefully acknowledges the financial support from the DST-Inspire Fellowship (No: DST/INSPIRE Fellowship/2012/690) New Delhi, India. We thank Dr. V. Sujatha for providing UV–Vis spectral facilities.
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Ramesh, R., Maheswari, S., Murugesan, S. et al. Catalyst-free one-pot synthesis and antioxidant evaluation of highly functionalized novel 1,4-dihydropyridine derivatives. Res Chem Intermed 41, 8233–8243 (2015). https://doi.org/10.1007/s11164-014-1887-z
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DOI: https://doi.org/10.1007/s11164-014-1887-z