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Synthesis of Novel Organic Compounds from Cyanuric Chloride Containing 1-(4-(7-Chloroquinolin-4-ylamino)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one Chalcone for Biological Applications
Corresponding Author(s) : A. Arun
Asian Journal of Chemistry,
Vol. 34 No. 5 (2022): Vol 34 Issue 5, 2022
Abstract
This article reported the synthesis of triazine having quinoline chalcone moiety and its derivatives. Cyanuric chloride, 1-(4-(7-chloroquinolin-4-ylamino)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one (KKC), aniline, 4-nitro aniline and 1-naphthol used for the synthesis. Triazine having chlorine atom was periodically replaced by the above materials to synthesize the desired product. Synthesized triazine based organic molecules were characterized using elemental analysis, FT-IR, 1H NMR and UV-visible spectroscopic techniques. Antibacterial activity of synthesized compounds was found on Gram-positive and Gram-negative bacteria by utilizing MIC method, most of the synthesized compound shows higher activity on Gram-positive bacteria Staphylococcus aureus with the value of 7.81 (mg/mL) than Gram-negative Escherichia coli. The presence of quinoline chalcone moiety and electron rich species responsible for higher antibacterial activity of the compounds on the tested bacteria.
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N.C. Desai, A.H. Makwana and K.M. Rajpara, J. Saudi Chem. Soc., 20, S334 (2016); https://doi.org/10.1016/j.jscs.2012.12.004
Z.E. Koc, H. Bingol, A.O. Saf, E. Torlak and A. Coskun, J. Hazard. Mater., 183, 251 (2010); https://doi.org/10.1016/j.jhazmat.2010.07.018
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R. Menicagli, S. Samaritani, G. Signore, F. Vaglini and L. Dalla Via, J. Med. Chem., 47, 4649 (2004); https://doi.org/10.1021/jm0495374
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R.S. Shinde, S.A. Dake and R.P. Pawar, Antiinfect. Agents, 17, 7 (2019); https://doi.org/10.2174/2211352517666190710115111
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R. Selvaraj, J. Suresh and A. Arun, Asian J. Chem., 32, 408 (2020); https://doi.org/10.14233/ajchem.2020.22461
A.A. Ouameur and H.A. Tajmir-Riahi, J. Biol. Chem., 279, 42041 (2004); https://doi.org/10.1074/jbc.M406053200
D.K. Jangir, S. Charak, R. Mehrotra and S. Kundu, J. Photochem. Photobiol. B, 105, 143 (2011); https://doi.org/10.1016/j.jphotobiol.2011.08.003
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K.D. Thomas, A.V. Adhikari, I.H. Chowdhury, T. Sandeep, R. Mahmood, B. Bhattacharya and E. Sumesh, Eur. J. Med. Chem., 46, 4834 (2011); https://doi.org/10.1016/j.ejmech.2011.07.049
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I. Petitpas, A.A. Bhattacharya, S. Twine, M. East and S. Curry, J. Biol. Chem., 276, 22804 (2001); https://doi.org/10.1074/jbc.M100575200
S.G. Charati, A.Y. Houde, S.S. Kulkarni and M.G. Kulkarni, J. Polym. Sci., B, Polym. Phys., 29, 921 (1991); https://doi.org/10.1002/polb.1991.090290803
K.I. Aly, Polym. Int., 47, 483 (1998); https://doi.org/10.1002/(SICI)1097-0126(199812)47:4<483::AID PI91>3.0.CO;2-F
B. Kalpana and R. Nanthini, Asian J. Chem., 31, 2341 (2019); https://doi.org/10.14233/ajchem.2019.21997
M. Thillainayagam, L. Pandian, K.K. Murugan, V. Vijayaparthasarathi, S. Sundaramoorthy, A. Anbarasu and S. Ramaiah, J. Biomol. Struct. Dyn., 33, 961 (2015); https://doi.org/10.1080/07391102.2014.920277
N. Balakrishn, M. Srivastava and P. Tiwari, Pak. J. Biol. Sci., 16, 1403 (2013); https://doi.org/10.3923/pjbs.2013.1403.1406
S. Prasad, R.S. Kashyap, J.Y. Deopujari, H.J. Purohit, G.M. Taori and H.F. Daginawala, BMC Complement. Altern. Med., 7, 36 (2007); https://doi.org/10.1186/1472-6882-7-36
T. Rabi and R.C. Gupta, Int. J. Pharmacol., 33, 359 (1995).
P. Uma, J. Suresh, R. Selvaraj, S. Karthik and A. Arun, J. Biomater. Sci. Polym. Ed., 26, 128 (2015); https://doi.org/10.1080/09205063.2014.985022