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Synthesis, Molecular Docking and Antimicrobial Studies of Some Novel 1,4-Dihydropyridine Derivatives
Corresponding Author(s) : G. Ramalingam
Asian Journal of Chemistry,
Vol. 31 No. 12 (2019): Vol 31 Issue 12
Abstract
Three components one pot synthesis of some novel triazole substituted 1,4-dihydropyridine compounds from the simple condensation reaction of ethyl acetoacetate, 4-amino triazole and aromatic aldehyde has been demonstrated using on low cost and efficient acetic acid catalyst in solvent free condition followed by microwave irradiation method. The newly synthesized 1,4-dihydropyridine compounds exhibit in excellent yield. The synthesized dihydropyridine derivatives are screened for antimicrobial properties and molecular docking study.
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- A. Hantzch, Chem. Ber., 14, 1637 (1881); https://doi.org/10.1002/cber.18810140214.
- N. Razzaghi-Asl, R. Miri and O. Firuzi, Iran. J. Pharm. Res., 15, 413 (2016).
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- S.F. Flaim and R. Zelis, Fed. Proc., 40, 2877 (1981).
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- R. Boer and V. Gekeler, Drugs Fut., 20, 499 (1995).
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- A. Debache, R. Boulcina, A. Belfaitah, S. Rhouati and B. Carboni, Synett., 509 (2008); https://doi.org/10.1055/s-2008-1032093.
- N. Koukabi, E. Kolvari, M.A. Zolfigol, A. Khazaei, B.S. Shaghasemi and B. Fasahati Adv. Synth. Catal., 354, 2001 (2012); https://doi.org/10.1002/adsc.201100352.
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- K.C. Khatri, D.S. Rekunge and G.U. Chaturbhuj, Tetrahedron Lett., 58, 1240 (2017).
- 22 S. Ko, M.N.V. Sastry, C. Lin and C.-F. Yao, Tetrahedron Lett., 46, 5771 (2005); https://doi.org/10.1016/j.tetlet.2005.05.148.
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- R.A. Mekheimer, A.A. Hameed and K.U. Sadek, Green Chem., 10, 592 (2008); https://doi.org/10.1039/b715126h.
- S.T. Patel, J.M. Percy and R.D. Wilkes, J. Org. Chem., 61, 166 (1996); https://doi.org/10.1021/jo951516h.
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References
A. Hantzch, Chem. Ber., 14, 1637 (1881); https://doi.org/10.1002/cber.18810140214.
N. Razzaghi-Asl, R. Miri and O. Firuzi, Iran. J. Pharm. Res., 15, 413 (2016).
S. Gullapalli and P. Ramarao, J. Nephropharmacol., 42, 467 (2002); https://doi.org/10.1016/S0028-3908(01)00200-3.
E.K. Ozer, M.G. Gunduz, A. El-Khouly, Y. Sara, R. Simsek, A.B. Iskit and C. Safak, Turk. J. Biochem., 43, 578 (2017); https://doi.org/10.1515/tjb-2016-0247.
A.M. Vijesh, A.M. Isloor, S.K. Peethambar, K.N. Shivananda, T. Arulmoli and N.A. Isloor, J. Eur. Med. Chem., 46, 5591 (2011); https://doi.org/10.1016/j.ejmech.2011.09.026.
H.-A.S. Abbas, H.N. Hafez and A.-R.B.A. El-Gazzar, J. Eur. Med. Chem., 46, 21 (2011); https://doi.org/10.1016/j.ejmech.2010.09.071.
A. Idhayadhulla, R.S. Kumar, A.J.A. Nasser, S. Kavimani and S. Indhumathy, Pharm. Chem. J., 49, 463 (2015); https://doi.org/10.1007/s11094-015-1305-x.
F. Bossert, H. Meyer and E. Wehinger, J. Angew. Chem. Int. Ed. Engl., 20, 762 (1981); https://doi.org/10.1002/anie.198107621.
H. Nakayama and Y. Kanaoka, Heterocycles, 42, 901 (1996); https://doi.org/10.3987/REV-95-SR4.
G.S. Marks, B.E. McLaughlin, H.J. Vreman, D.K. Stevenson, K. Nakatsu, J.F. Brien and S.C. Pang, J. Cardiovasc. Pharmacol., 30, S1 (1997); https://doi.org/10.1097/00005344-199707000-00001.
S.F. Flaim and R. Zelis, Fed. Proc., 40, 2877 (1981).
P.A. Van Zwieten, Blood Press, 7(supp1), 5 (1998); https://doi.org/10.1080/080370598438999.
T. Godfraind, R. Miller and M. Wibo, Pharmacol. Rev., 38, 321 (1986).
G. Duburs and A. Sausins, Heterocycles, 27, 269 (1988); https://doi.org/10.3987/REV-87-370.
R. Mannhold, B. Jablonka, W. Voigt, K. Schönafinger and E. Schraven, Eur. Med. Chem., 27, 229 (1992); https://doi.org/10.1016/0223-5234(92)90006-M.
R. Boer and V. Gekeler, Drugs Fut., 20, 499 (1995).
M.G. Sharma, D.P. Rajani and H.M. Patel, J. Royal Chem. Sci., 4, 170006 (2017); https://doi.org/10.1098/rsos.170006.
A. Debache, R. Boulcina, A. Belfaitah, S. Rhouati and B. Carboni, Synett., 509 (2008); https://doi.org/10.1055/s-2008-1032093.
N. Koukabi, E. Kolvari, M.A. Zolfigol, A. Khazaei, B.S. Shaghasemi and B. Fasahati Adv. Synth. Catal., 354, 2001 (2012); https://doi.org/10.1002/adsc.201100352.
C. Faydali, H. Demirrhan, M. Arslan, M. Fuckislamoglu and M. Zengin, J. Turk. Chem., 33, 769 (2009).
V. Sivamurugan, R.S. Kumar, M. Palanichamy and V. Murugesan, J. Heterocycl. Chem., 42, 969 (2005); https://doi.org/10.1002/jhet.5570420534.
L.-M. Wang, J. Sheng, L. Zhang, J.-W. Han, Z.-Y. Fan, H. Tian and C.-T. Qian, Tetrahedron, 61, 1539 (2005); https://doi.org/10.1016/j.tet.2004.11.079.
K.C. Khatri, D.S. Rekunge and G.U. Chaturbhuj, Tetrahedron Lett., 58, 1240 (2017).
22 S. Ko, M.N.V. Sastry, C. Lin and C.-F. Yao, Tetrahedron Lett., 46, 5771 (2005); https://doi.org/10.1016/j.tetlet.2005.05.148.
G. Sabitha, G.S.K.K. Reddy, C.S. Reddy and J.S. Yadav, Tetrahedron Lett., 44, 4129 (2003); https://doi.org/10.1016/S0040-4039(03)00813-X.
R.A. Mekheimer, A.A. Hameed and K.U. Sadek, Green Chem., 10, 592 (2008); https://doi.org/10.1039/b715126h.
S.T. Patel, J.M. Percy and R.D. Wilkes, J. Org. Chem., 61, 166 (1996); https://doi.org/10.1021/jo951516h.
A. Rahamati, A. Shaabani, A.H. Rezayan and M. Sharifi, Monatsh. Chem., 137, 77 (2006); https://doi.org/10.1007/s00706-005-0405-9.
N.M. Evdokimov, I.V. Magedov, A.S. Kireev and A. Kornienko, Org. Lett., 8, 899 (2006); https://doi.org/10.1021/ol052994+.
M. Kidwai, S. Saxena, R. Mohan and R. Venkataramanan, J. Chem. Soc., Perkin Trans. II, 1845 (2002); https://doi.org/10.1039/B205539M.
C. Pramanik, P. Patil, S. Kotharkar, N.K. Tripathy and M.K. Gurjar, Tetrahedron Lett., 3043, 58 (2013); https://doi.org/10.1016/j.tetlet.2013.03.090.