Copyright (c) 2021 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Antimicrobial, Structure-Activity Relationship and Computational Studies of Some Synthesized Chalcone Derivatives
Corresponding Author(s) : Md Mizanur Rahman Badal
Asian Journal of Chemistry,
Vol. 33 No. 3 (2021): Vol 33 Issue 3
Abstract
Several chalcones viz. 1,3-diaryl-2-propane-1-one (1a), 3-(4-hydroxy phenyl)-1-phenyl-2-propane-1-one (1b), 3-(4-amino-phenyl)-1-phenyl-2-propane-1-one (1c) and their derivatives 2-ethoxy-4,6-diphenyl-4H-pyran-3-carboxylic acid ethyl ester (2a), 4-(4-hydroxy-phenyl)-7,7-dimethyl-2-phenyl-4,6,7,8-tetrahydro-chromen-5-one (2b) and 7-(4-amino-phenyl)-5-phenyl-1,5-dihydropyrano[2,3-d]pyrimidine-2,4-dione (2c) have been synthesized following both conventional and microwave irradiation methods. The structures of the isolated compounds were elucidated on the basis of UV-visible, FTIR, 1H NMR spectral data. The antimicrobial results showed some remarkable facts about the structure–activity relationship, which states that the electronic atmosphere around the chalcone derivative moieties and substituents considerably affect the antimicrobial potential of the synthesized compounds. Theoretical calculation as well as antimicrobial activity of the compounds were also studied.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- M. Xu, P. Wu, F. Shen, J. Ji and K.P. Rakesh, Bioorg. Chem., 91, 103133 (2019); https://doi.org/10.1016/j.bioorg.2019.103133
- J. Amanaganti and N.J.P. Subhashini, Int. J. Chem. Sci., 11, 1335 (2013).
- M.N. Gomes, E.N. Muratov, M. Pereira, J.C. Peixoto, L.P. Rosseto, P.V.L. Cravo, C.H. Andrade and B.J. Neves, Molecules, 22, 1210 (2017); https://doi.org/10.3390/molecules22081210
- S.V. Kostanecki and J. Tambor, Chem. Ber., 32, 1921 (1899); https://doi.org/10.1002/cber.18990320293
- A. Crozier, I.B. Jaganath and M.N. Clifford, Nat. Prod. Rep., 26, 1001 (2009); https://doi.org/10.1039/b802662a
- F. Bhabhor, K. Satish, H. Variya and V. Panchal, Int. Lett. Chem. Phys. Astron., 63, 83 (2016); https://doi.org/10.18052/www.scipress.com/ILCPA.63.83
- E.S.I. El-Desoky, E.M. Keshk, A.A. El-Sawi, M.A. Abozeid, L.A. Abouzeid and A.R.H. Abdel-Rahman, Saudi Pharm. J., 26, 852 (2018); https://doi.org/10.1016/j.jsps.2018.03.013
- P. Yadav, K. Lal, A. Kumar, S.K. Guru, S. Jaglan and S. Bhushan, Eur. J. Med. Chem., 126, 944 (2017); https://doi.org/10.1016/j.ejmech.2016.11.030
- D. Kozlowski, P. Trouillas, C. Calliste, P. Marsal, R. Lazzaroni and J.L. Duroux, J. Phys. Chem. A, 111, 1138 (2007);https://doi.org/10.1021/jp066496+
- Z. Rozmer and P. Perjési, Phytochem. Rev., 15, 87 (2016); https://doi.org/10.1007/s11101-014-9387-8
- Y.S. Mary, Y.S. Mary and A.C. Ciltas, Struct. Chem., 32, 19 (2020); https://doi.org/10.1007/s11224-020-01609-6
- E.G.W.M. Schijlen, C.H. Ric De Vos, A.J. Van Tunen and A.G. Bovy, Phytochemistry, 65, 2631 (2004);https://doi.org/10.1016/j.phytochem.2004.07.028
- N.C. Veitch and R.J. Grayer, Nat. Prod. Rep., 25, 555 (2008); https://doi.org/10.1039/b718040n
- S.K. Kumar, E. Hager, C. Pettit, H. Gurulingappa, N.E. Davidson and S.R. Khan, J. Med. Chem., 46, 2813 (2003);https://doi.org/10.1021/jm030213+
- P.B. Reddy, M.B.M. Reddy, R. Reddy, S. Chhajed and P.P. Gupta, Struct. Chem., 31, 2249 (2020);https://doi.org/10.1007/s11224-020-01571-3
- R. Mani and V. Natesan, Phytochemistry, 145, 187 (2018); https://doi.org/10.1016/j.phytochem.2017.09.016
- E.M. Sharshira and N.M.M. Hamada, Molecules, 17, 4962 (2012); https://doi.org/10.3390/molecules17054962
- C.G.D. Raj, B.K. Sarojini, S. Hegde, S. Sreenivasa, Y.S. Ravikumar, V. Bhanuprakash, Y. Revanaiah and R. Ragavendra, Med. Chem. Res.,22, 2079 (2013); https://doi.org/10.1007/s00044-012-0193-9
- S.L. Gaonkar and U.N. Vignesh, Res. Chem. Intermed., 43, 6043 (2017); https://doi.org/10.1007/s11164-017-2977-5
- G.R. De Oliveira, H.C.B. De Oliveira, W.A. Silva, V.H.C. Da Silva, J.R. Sabino and F.T. Martins, Struct. Chem., 23, 1667 (2012); https://doi.org/10.1007/s11224-012-9972-7
- M.M.R. Badal, H.M. Ashekul Islam, M. Maniruzzaman and M. Abu Yousuf, ACS Omega, 5, 22978 (2020); https://doi.org/10.1021/acsomega.0c02556
- J. Yan, J. Chen, S. Zhang, J. Hu, L. Huang and X. Li, J. Med. Chem.,59, 5264 (2016); https://doi.org/10.1021/acs.jmedchem.6b00021
- E.J. Baron and S. Antonson, Clin. Infect. Dis., 24, 537 (1997); https://doi.org/10.1093/clinids/24.3.537
- D.M. Livermore and D.F.J. Brown, J. Antimicrob. Chemother., 48(S1), 59 (2001); https://doi.org/10.1093/jac/48.suppl_1.59
- C.C. Sanders, W.E. Sanders and R.V. Goering, Antimicrob. Agents Chemother., 21, 968 (1982); https://doi.org/10.1128/AAC.21.6.968
- M.J. Frisch, G.W. Trucks, H.B. Schlegal, G.E. Scuseria, M.A. Robb, J.R. Cheesman, V.G. Zakrzewski, J.A. Montgomerg Jr., R.E. Stratmann,J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, R. Cammi, B. Mennucci, M.Cossi, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, N. Rega, P. Salvador, J.J. Dannenberg, D.K. Malich, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stetanov, A. Liashenko, G. Liu, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, M.W. Wong, J.L. Andres, C. Gonzalez, W. Chen, M. Head-Gordon, E.S. Replogle and J.A. Pople, GAUSSIAN 09, Revision A 11.4, Gaussian, Inc., Pittsburgh PA (2009).
- M.S. Cubberley and B.L. Iverson, J. Am. Chem. Soc., 123, 7560 (2001); https://doi.org/10.1021/ja015817m
- H.E. Gottlieb, V. Kotlyar and A. Nudelman, J. Org. Chem., 62, 7512 (1997); https://doi.org/10.1021/jo971176v
- R.G. Pearson, J. Org. Chem., 54, 1423 (1989); https://doi.org/10.1021/jo00267a034
- A. Nitti, M. Signorile, M. Boiocchi, G. Bianchi, R. Po and D. Pasini, J. Org. Chem., 81, 11035 (2016); https://doi.org/10.1021/acs.joc.6b01922
References
M. Xu, P. Wu, F. Shen, J. Ji and K.P. Rakesh, Bioorg. Chem., 91, 103133 (2019); https://doi.org/10.1016/j.bioorg.2019.103133
J. Amanaganti and N.J.P. Subhashini, Int. J. Chem. Sci., 11, 1335 (2013).
M.N. Gomes, E.N. Muratov, M. Pereira, J.C. Peixoto, L.P. Rosseto, P.V.L. Cravo, C.H. Andrade and B.J. Neves, Molecules, 22, 1210 (2017); https://doi.org/10.3390/molecules22081210
S.V. Kostanecki and J. Tambor, Chem. Ber., 32, 1921 (1899); https://doi.org/10.1002/cber.18990320293
A. Crozier, I.B. Jaganath and M.N. Clifford, Nat. Prod. Rep., 26, 1001 (2009); https://doi.org/10.1039/b802662a
F. Bhabhor, K. Satish, H. Variya and V. Panchal, Int. Lett. Chem. Phys. Astron., 63, 83 (2016); https://doi.org/10.18052/www.scipress.com/ILCPA.63.83
E.S.I. El-Desoky, E.M. Keshk, A.A. El-Sawi, M.A. Abozeid, L.A. Abouzeid and A.R.H. Abdel-Rahman, Saudi Pharm. J., 26, 852 (2018); https://doi.org/10.1016/j.jsps.2018.03.013
P. Yadav, K. Lal, A. Kumar, S.K. Guru, S. Jaglan and S. Bhushan, Eur. J. Med. Chem., 126, 944 (2017); https://doi.org/10.1016/j.ejmech.2016.11.030
D. Kozlowski, P. Trouillas, C. Calliste, P. Marsal, R. Lazzaroni and J.L. Duroux, J. Phys. Chem. A, 111, 1138 (2007);https://doi.org/10.1021/jp066496+
Z. Rozmer and P. Perjési, Phytochem. Rev., 15, 87 (2016); https://doi.org/10.1007/s11101-014-9387-8
Y.S. Mary, Y.S. Mary and A.C. Ciltas, Struct. Chem., 32, 19 (2020); https://doi.org/10.1007/s11224-020-01609-6
E.G.W.M. Schijlen, C.H. Ric De Vos, A.J. Van Tunen and A.G. Bovy, Phytochemistry, 65, 2631 (2004);https://doi.org/10.1016/j.phytochem.2004.07.028
N.C. Veitch and R.J. Grayer, Nat. Prod. Rep., 25, 555 (2008); https://doi.org/10.1039/b718040n
S.K. Kumar, E. Hager, C. Pettit, H. Gurulingappa, N.E. Davidson and S.R. Khan, J. Med. Chem., 46, 2813 (2003);https://doi.org/10.1021/jm030213+
P.B. Reddy, M.B.M. Reddy, R. Reddy, S. Chhajed and P.P. Gupta, Struct. Chem., 31, 2249 (2020);https://doi.org/10.1007/s11224-020-01571-3
R. Mani and V. Natesan, Phytochemistry, 145, 187 (2018); https://doi.org/10.1016/j.phytochem.2017.09.016
E.M. Sharshira and N.M.M. Hamada, Molecules, 17, 4962 (2012); https://doi.org/10.3390/molecules17054962
C.G.D. Raj, B.K. Sarojini, S. Hegde, S. Sreenivasa, Y.S. Ravikumar, V. Bhanuprakash, Y. Revanaiah and R. Ragavendra, Med. Chem. Res.,22, 2079 (2013); https://doi.org/10.1007/s00044-012-0193-9
S.L. Gaonkar and U.N. Vignesh, Res. Chem. Intermed., 43, 6043 (2017); https://doi.org/10.1007/s11164-017-2977-5
G.R. De Oliveira, H.C.B. De Oliveira, W.A. Silva, V.H.C. Da Silva, J.R. Sabino and F.T. Martins, Struct. Chem., 23, 1667 (2012); https://doi.org/10.1007/s11224-012-9972-7
M.M.R. Badal, H.M. Ashekul Islam, M. Maniruzzaman and M. Abu Yousuf, ACS Omega, 5, 22978 (2020); https://doi.org/10.1021/acsomega.0c02556
J. Yan, J. Chen, S. Zhang, J. Hu, L. Huang and X. Li, J. Med. Chem.,59, 5264 (2016); https://doi.org/10.1021/acs.jmedchem.6b00021
E.J. Baron and S. Antonson, Clin. Infect. Dis., 24, 537 (1997); https://doi.org/10.1093/clinids/24.3.537
D.M. Livermore and D.F.J. Brown, J. Antimicrob. Chemother., 48(S1), 59 (2001); https://doi.org/10.1093/jac/48.suppl_1.59
C.C. Sanders, W.E. Sanders and R.V. Goering, Antimicrob. Agents Chemother., 21, 968 (1982); https://doi.org/10.1128/AAC.21.6.968
M.J. Frisch, G.W. Trucks, H.B. Schlegal, G.E. Scuseria, M.A. Robb, J.R. Cheesman, V.G. Zakrzewski, J.A. Montgomerg Jr., R.E. Stratmann,J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, R. Cammi, B. Mennucci, M.Cossi, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, N. Rega, P. Salvador, J.J. Dannenberg, D.K. Malich, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stetanov, A. Liashenko, G. Liu, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, M.W. Wong, J.L. Andres, C. Gonzalez, W. Chen, M. Head-Gordon, E.S. Replogle and J.A. Pople, GAUSSIAN 09, Revision A 11.4, Gaussian, Inc., Pittsburgh PA (2009).
M.S. Cubberley and B.L. Iverson, J. Am. Chem. Soc., 123, 7560 (2001); https://doi.org/10.1021/ja015817m
H.E. Gottlieb, V. Kotlyar and A. Nudelman, J. Org. Chem., 62, 7512 (1997); https://doi.org/10.1021/jo971176v
R.G. Pearson, J. Org. Chem., 54, 1423 (1989); https://doi.org/10.1021/jo00267a034
A. Nitti, M. Signorile, M. Boiocchi, G. Bianchi, R. Po and D. Pasini, J. Org. Chem., 81, 11035 (2016); https://doi.org/10.1021/acs.joc.6b01922