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Green Synthetic Protocol for (E)-1-Aryl-3-(2-morpholinoquinolin-3-yl)prop-2-en-1-ones and Their Antimicrobial Activity
Corresponding Author(s) : Venkateswara Rao Anna
Asian Journal of Chemistry,
Vol. 31 No. 9 (2019): Vol 31 Issue 9
Abstract
We report here an easy, efficient and green synthetic protocol for the (E)-1-aryl-3-(2-morpholinoquinolin-3-yl)prop-2-en-1-ones by the Claisen-Schmidt condensation of 2-morpholinoquinoline-3-carbaldehyde and different substituted acetophenones by using 1-butyl-3-methylimidazolium tetrafluoroborate (Bmim)BF4. The compounds were characterized by using 1H NMR, 13C NMR and mass spectral data and screened there in vitro antimicrobial activity against different bacterial and fungal organisms.
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- Y.-L. Chen, H.-M. Hung, C.-M. Lu, K.-C. Li and C.-C. Tzeng, Bioorg. Med. Chem., 12, 6539 (2004); https://doi.org/10.1016/j.bmc.2004.09.025.
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References
Y.-L. Chen, H.-M. Hung, C.-M. Lu, K.-C. Li and C.-C. Tzeng, Bioorg. Med. Chem., 12, 6539 (2004); https://doi.org/10.1016/j.bmc.2004.09.025.
Z. Luo, C. Zeng, W. Fang, H. He and C. Wang, Chem. Res. Chin. Univ., 25, 841 (2009).
N.C. Desai, B.Y. Patel and B.P. Dave, Med. Chem. Res., 26, 109 (2017); https://doi.org/10.1007/s00044-016-1732-6.
R.S. Keri and S.A. Patil, Biomed. Pharmacother., 68, 1161 (2014); https://doi.org/10.1016/j.biopha.2014.10.007.
C. de la Guardia, D. Stephens, H. Dang, M. Quijada, O. Larionov and R. Lleonart, Molecules, 23, 672 (2018); https://doi.org/10.3390/molecules23030672.
M. Foley and L. Tilley, Pharmacol. Ther., 79, 55 (1998); https://doi.org/10.1016/S0163-7258(98)00012-6.
M.O. Püsküllü, B. Tekiner and S. Suzen, Mini Rev. Med. Chem., 13, 365 (2013); https://doi.org/10.2174/138955713804999793.
S. Mukherjee and M. Pal, Curr. Med. Chem., 20, 4386 (2013); https://doi.org/10.2174/09298673113209990170.
E. García, J.C. Coa, E. Otero, M. Carda, I.D. Vélez, S.M. Robledo and W.I. Cardona, Med. Chem. Res., 27, 497 (2018); https://doi.org/10.1007/s00044-017-2076-6.
H. Bektas, S. Ceylan, N. Demirbas, S. Alpay-Karaoglu and B.B. Sökmen, Med. Chem. Res., 22, 3629 (2013); https://doi.org/10.1007/s00044-012-0318-1.
A. Ahmadi, M. Khalili, R. Hajikhani, N. Safari and B. Nahri-Niknafs, Med. Chem. Res., 21, 3532 (2012); https://doi.org/10.1007/s00044-011-9891-y.
D.D. Bozic, M. Milenkovic, B. Ivkovic and I. Cirkovic, Indian J. Med. Res., 140, 130 (2014).
C. Karthikeyan, N.S.H. Narayana Moorthy, S. Ramasamy, U. Vanam, E. Manivannan, D. Karunagaran and P. Trivedi, Recent Patents Anticancer Drug Discov., 10, 97 (2014); https://doi.org/10.2174/1574892809666140819153902.
H.K. Hsieh, L.T. Tsao, J.P. Wang and C.N. Lin, J. Pharm. Pharmacol., 52, 163 (2000); https://doi.org/10.1211/0022357001773814.
C.T. Hsieh, T.J. Hsieh, M. El-Shazly, D.W. Chuang, Y.H. Tsai, C.T. Yen, S.F. Wu, Y.C. Wu and F.R. Chang, Bioorg. Med. Chem. Lett., 22, 3912 (2012); https://doi.org/10.1016/j.bmcl.2012.04.108.
B.A. Hathaway, J. Chem. Educ., 64, 367 (1987); https://doi.org/10.1021/ed064p367.
M.A. Bigdeli, G.H. Mahdavinia, S. Jafari and H. Hazarkhani, Catal. Commun., 8, 2229 (2007); https://doi.org/10.1016/j.catcom.2007.05.010.
S. Bhagat, R. Sharma and A.K. Chakraborti, J. Mol. Catal. Chem., 260, 235 (2006); https://doi.org/10.1016/j.molcata.2006.07.018.
A. Fischer, P. Makowski, J.-O. Müller, M. Antonietti, A. Thomas and F. Goettmann, ChemSusChem, 1, 444 (2008); https://doi.org/10.1002/cssc.200800019.
T. Mukaiyama, K. Narasaka and H. Hokonoki, J. Am. Chem. Soc., 91, 4315 (1969); https://doi.org/10.1021/ja01043a066.