Copyright (c) 2020 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis, Characterization and Enzyme Inhibition Activity of Organophosphorus Trichalcones Containing Core-Phosphate Moiety
Corresponding Author(s) : Dnyaneshwar S. Wankhede
Asian Journal of Chemistry,
Vol. 32 No. 1 (2020): Vol 32 Issue 1
Abstract
Facile synthesis of various organophosphorus trichalcones, possessing substantial insecticidal activity, by using tris(4-acetylphenyl)-phosphate (3) and substituted benzaldehydes as a precursor has been reported. Key precursor 3 has been prepared under mild conditions in presence of tetrabutylammonium bromide (TBAB) as a phase transfer catalyst. All the synthesized compounds (5a-h) were screened for their antibacterial activity and inhibition of α-amylase of insect pest, Tribolium castaneum (Herbst) (Coleoptera: Tenebrionadeae). Biological activity evaluation study revealed that among all the compounds screened, compound 5g found to have promising inhibition of α-amylase of insect pest, Tribolium castaneum. All the synthesized compounds revealed insignificant antimicrobial activity against pathogenic bacteria even at 500 μg/mL.
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H.M. Ali and Z.H. Zidan, Phosphorus Sulfur Silicon Rel. Elem., 163, 41 (2000); https://doi.org/10.1080/10426500008046609.
S.E. Denmark and R.A. Stavenger, Acc. Chem. Res., 33, 432 (2000); https://doi.org/10.1021/ar960027g.
P.V.G. Reddy, C.S. Reddy and C.N. Raju, Chem. Pharm. Bull. (Tokyo), 51, 860 (2003); https://doi.org/10.1248/cpb.51.860.
K.A. Kumar, C.S. Reddy and C.D. Reddy, Indian J. Chem., 42A, 2589 (2003).
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R. Chandra, O.P. Pandey and S.K. Sengupta, J. Agric. Food Chem., 53, 2181 (2005); https://doi.org/10.1021/jf040134m.
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D.B. Barr and J. Angerer, Environ. Health Perspect., 114, 1763 (2006); https://doi.org/10.1289/ehp.9062.
N. Cetin, E. Cetin, G. Eraslan and A. Bilgili, Res. Vet. Sci., 82, 405 (2007); https://doi.org/10.1016/j.rvsc.2006.08.002.
F. Lai, H. Wang and R. Chen, Chem. J. Chinese Univ., 13, 191 (1992).
H. Cao, H. Wang, F. Yang, J. Wang and Z. Lue, Nongyaoxue Xuebao, 5, 21 (2003).
T.K. Chattapadhyay and R.L. Gupta, Indian J. Chem., 41B, 1718 (2002).
H. Ishikawa and K. Morita, J. Pestic. Sci., 18, 197 (1993); https://doi.org/10.1584/jpestics.18.2_197.
D. Shi, J. Liu, Z. Sheng, X. Liu and H. Wu, Nongyaoxue Xuebao, 4, 79 (2002).
D.B. Barr, R. Bravo, G. Weerasekera, L.M. Caltabiano, R.D. Whitehead Jr., A.O. Olsson, S.P. Caudill, S.E. Schober, J.L. Pirkle, E.J. Sampson, R.J. Jackson and L.L. Needham, Environ. Health Perspect., 112, 186 (2004); https://doi.org/10.1289/ehp.6503.
L. Keralliedde, R.J. Feldman, L.O. Henderson and T. Marrs, Organophosphates and Health, Imperial College Press: London (2001).
S. Karanth, K. Olivier Jr., J. Liu and C. Pope, Toxicol. Appl. Pharmacol., 177, 247 (2001); https://doi.org/10.1006/taap.2001.9312.
L.D. Quin, A Guide to Organophosphorus Chemistry, John Wiley & Sons Inc.: New York (2000).
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K. Kaniappan and S.C. Murugavel, J. Appl. Polym. Sci., 111, 1606 (2009); https://doi.org/10.1002/app.29190.
L.G. Costa, Toxicol. Sci., 162, 24 (2018); https://doi.org/10.1093/toxsci/kfx266.
R.T. Delfino, T.S. Ribeiro and J.D. Figueroa-Villar, J. Braz. Chem. Soc., 20, 407 (2009); https://doi.org/10.1590/S0103-50532009000300003.
P. Jhajharia, M.K. Samota, K. Soni and G. Seth, Phosphorus Sulfur Silicon Rel. Elem., 184, 315 (2009); https://doi.org/10.1080/10426500802111579.
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P.J. Thornton, H. Kadri, A. Miccoli and Y. Mehellou, J. Med. Chem., 59, 10400 (2016); https://doi.org/10.1021/acs.jmedchem.6b00523.
A.D. Sagar, D.S. Patil and B.P. Bandgar, Synth. Commun., 30, 1719 (2000); https://doi.org/10.1080/00397910008087214.
S. Pareek, S. Vyas, G. Seth and P.C. Vyas, Heteroatom Chem., 20, 246 (2009); https://doi.org/10.1002/hc.20533.
G. Keglevich, A. Grun, E. Balint, N. Zsuzsa Kiss and E. Jablonkai, Curr. Org. Chem., 17, 545 (2013); https://doi.org/10.2174/1385272811317050009.
F.G. Khan, M.V. Yadav and A.D. Sagar, Med. Chem. Res., 23, 2633 (2014); https://doi.org/10.1007/s00044-013-0837-4.
J.L. Zettler, J. Econ. Entomol., 84, 763 (1991); https://doi.org/10.1093/jee/84.3.763.
P. Bernfeld, Methods Enzymol., 1, 149 (1955); https://doi.org/10.1016/0076-6879(55)01021-5.
P.S. Kulkarni, P.M. Swami and P.K. Zubaidha, Synth. React. Inorg. Met.-Org. Nano-Met. Chem., 43, 617 (2013); https://doi.org/10.1080/15533174.2012.752392.
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