Copyright (c) 2021 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis of (E)-1-(2,4-Bis((1-phenyl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3-phenylprop-2-en-1-one Derivatives and their Antimicrobial Activity
Corresponding Author(s) : Pochampally Jalapathi
Asian Journal of Chemistry,
Vol. 33 No. 10 (2021): Vol 33 Issue 10, 2021
Abstract
A new series of chalcone based bis 1,4-disubstituted 1,2,3-triazole heterocyclic molecules (6a-j) were synthesized via the reaction of 1-(2,4-bis((1-phenyl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)ethanone (6a-e) with substituted benzaldehyde. All the molecules were characterized by IR, 1H and 13C NMR and MS spectra spectral data. Compounds 6a-j were evaluated for their antimicrobial effects using a broth disc diffusion method. The compounds were evaluated for their in vitro antimicrobial potential against Gram-positive (Micrococcus luteus, Methicillin-resistant Staphylococcus aureus, Bacillus subtilis and Bacillus cereus), Gram-negative (Pseudomonas aeruginosa, Klebsiella pneumoniae, Escherichia coli and Proteus vulgaris) bacterial and fungal (Microsporum canis, Microsporum gypseum and Epidermophyton floccosum) strains by comparison of the reference drugs, zentamycin sulphate (antibacterial) and nystatin (antifungal). The screened compounds 6f, 6e, 6c and 6i were found to be the most active against all the tested bacterial and fungal strains.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- N.G.V. Aher, S.N. Pore, N. Mishra, A. Kumar, P.K. Shukla, A. Sharma and M.K. Bhat, Bioorg. Med. Chem. Lett., 19, 759 (2009); https://doi.org/10.1016/j.bmcl.2008.12.026
- X.L. Wang, K. Wan and C.H. Zhou, Eur. J. Med. Chem., 45, 4631 (2010); https://doi.org/10.1016/j.ejmech.2010.07.031
- A. Kamal, N. Shankaraiah, V. Devaiah, K. Laxma Reddy, A. Juvekar, S. Sen, N. Kurian and S. Zingde, Bioorg. Med. Chem. Lett., 18, 1468 (2008); https://doi.org/10.1016/j.bmcl.2007.12.063
- D.K. Kim, J. Kim and H.J. Park, Bioorg. Med. Chem. Lett., 14, 2401 (2004); https://doi.org/10.1016/j.bmcl.2004.03.024
- O. Ciofu and T. Tolker-Nielsen, Front. Microbiol., 10, 913 (2019); https://doi.org/10.3389/fmicb.2019.00913
- B.K. Singh, A.K. Yadav, B. Kumar, A. Gaikwad, S.K. Sinha, V. Chaturvedi and R.P. Tripathi, Carbohydr. Res., 343, 1153 (2008); https://doi.org/10.1016/j.carres.2008.02.013
- P.V. Chavan, K.S. Pandit, U.V. Desai, M.A. Kulkarni and P.P. Wadgaonkar, RSC Adv., 4, 42137 (2014); https://doi.org/10.1039/C4RA05080K
- H. Khalil, T. El Malah, A.I.A. El Maksoud, I. El Halfawy, A.A. El Rashedy and M. El Hefnawy, Front. Cell. Infect.Microbiol., 7, 304 (2017); https://doi.org/10.3389/fcimb.2017.00304
- I.E. Glowacka, G. Andrei, D. Schols, R. Snoeck and D.G. Piotrowska, Molecules, 20, 18789 (2015); https://doi.org/10.3390/molecules201018789
- H. Cheng, J. Wan, M.I. Lin, Y. Liu, X. Lu, J. Liu, Y. Xu, J. Chen, Z. Tu, Y.S.E. Cheng and K. Ding, J. Med. Chem., 55, 2144 (2012); https://doi.org/10.1021/jm2013503
- M. Saeedi, M. Mohammadi Khanaposhtani, P. Pourrabia, N. Razzaghi, R. Ghadimi, S. Imanparast, M.A. Faramarzi, F. Bandarian, E.N. Esfahani, M. Safavi, H. Rastegar, B. Larijani, M. Mahdavi and T. Akbarzadeh, Bioorg. Chem., 83, 161 (2019); https://doi.org/10.1016/j.bioorg.2018.10.023
- I. Mohammed, I.R. Kummetha, G. Singh, N. Sharova, G. Lichinchi, J. Dang, M. Stevenson and T.M. Rana, J. Med. Chem., 59, 7677 (2016); https://doi.org/10.1021/acs.jmedchem.6b00247
- Z. Zhou, T. Liu, G. Wu, D. Kang, Z. Fu, Z. Wang, E. De Clercq, C. Pannecouque, P. Zhan and X. Liu, Org. Biomol. Chem., 17, 3202 (2019); https://doi.org/10.1039/C9OB00032A
- X. Jiang, G. Wu, W.A. Zalloum, M.E. Meuser, A. Dick, L. Sun, C.H. Chen, D. Kang, L. Jing, R. Jia, S. Cocklin, K.-H. Lee, X. Liu and P. Zhan, RSC Adv., 9, 28961 (2019); https://doi.org/10.1039/C9RA05869A
- F.C. da Silva, M.C.B.V. de Souza, I.I.P. Frugulhetti, H.C. Castro, S.L.O. Souza, T.M.L. de Souza, D.Q. Rodrigues, A.M.T. Souza, P.A. Abreu and F. Passamani, Eur. J. Med. Chem., 44, 373 (2009); https://doi.org/10.1016/j.ejmech.2008.02.047
- F. Naaz, M.C. Preeti Pallavi, S. Shafi, N. Mulakayala, M. Shahar Yar and H.M. Sampath Kumar, Bioorg. Chem., 81, 1 (2018); https://doi.org/10.1016/j.bioorg.2018.07.029
- S. Haider, M.S. Alam, H. Hamid, S. Shafi, A. Nargotra, P. Mahajan, S. Nazreen, A.M. Kalle, C. Kharbanda, Y. Ali, A. Alam and A.K. Panda, Eur. J. Med. Chem., 70, 579 (2013); https://doi.org/10.1016/j.ejmech.2013.10.032
- F. Ahmadi, M.R. Ghayahbashi, M. Sharifzadeh, E. Alipoiur, S.N. Ostad, M. Vosooghi, H.R. Khademi and M. Amini, Med. Chem., 11, 69 (2014); https://doi.org/10.2174/1573406410666140613154507
- N. Batra, V. Rajendran, D. Agarwal, I. Wadi, P.C. Ghosh, R.D. Gupta and M. Nath, Chemistry Select, 3, 9790 (2018); https://doi.org/10.1002/slct.201801905
- E.O.J. Porta, I. Bofill Verdaguer, C. Perez, C. Banchio, M. Ferreira de Azevedo, A.M. Katzin and G.R. Labadie, MedChemComm, 10, 1599 (2019); https://doi.org/10.1039/C9MD00298G
- L. Savegnago, M. Sacramento, L.M.P. Brod, M.G. Fronza, N. Seus, E.J. Lenardão, M.W. Paixão and D. Alves, RSC Advances, 6, 8021 (2016); https://doi.org/10.1039/C5RA22445D
- T. Settypalli, V.R. Chunduri, A.K. Maddineni, N. Begari, R. Allagadda, P. Kotha and A.R. Chippada, New J. Chem., 43, 15435 (2019); https://doi.org/10.1039/C9NJ02580D
- D.S. Kapkoti, S. Singh, S. Luqman and R.S. Bhakuni, New J. Chem., 42, 5978 (2018); https://doi.org/10.1039/C7NJ04271J
- A. Singh, S.T. Saha, S. Perumal, M. Kaur and V. Kumar, ACS Omega, 3, 1263 (2018); https://doi.org/10.1021/acsomega.7b01755
- D.-J. Fu, S.-Y. Zhang, Y.-C. Liu, X.-X. Yue, J.-J. Liu, J. Song, R.-H. Zhao, F. Li, H.-H. Sun, Y.-B. Zhang and H.-M. Liu, MedChemComm, 7, 1664 (2016); https://doi.org/10.1039/C6MD00169F
- Z. Nowakowska, Eur. J. Med. Chem., 42, 125 (2007); https://doi.org/10.1016/j.ejmech.2006.09.019
- T. Akihisa, H. Tokuda, D. Hasegawa, M. Ukiya, Y. Kimura, F. Enjo, T. Suzuki and H. Nishino, J. Nat. Prod., 69, 38 (2006); https://doi.org/10.1021/np058080d
- K.L. Lahtchev, D.I. Batovska, P. Parushev, V.M. Ubiyvovk and A.A. Sibirny, Eur. J. Med. Chem., 43, 2220 (2008); https://doi.org/10.1016/j.ejmech.2007.12.027
- D.K. Mahapatra, S.K. Bharti and V. Asati, Eur. J. Med. Chem., 98, 69 (2015); https://doi.org/10.1016/j.ejmech.2015.05.004
- R. Kant, D. Kumar, D. Agarwal, R.D. Gupta, R. Tilak, S.K. Awasthi and A. Agarwal, Eur. J. Med. Chem., 113, 34 (2016); https://doi.org/10.1016/j.ejmech.2016.02.041
- P. Yadav, K. Lal, L. Kumar, A. Kumar, A. Kumar, A.K. Paul and R. Kumar, Eur. J. Med. Chem., 155, 263 (2018); https://doi.org/10.1016/j.ejmech.2018.05.055
- E.M. Guantai, K. Ncokazi, T.J. Egan, J. Gut, P.J. Rosenthal, P.J. Smith and K. Chibale, Bioorg. Med. Chem., 18, 8243 (2010); https://doi.org/10.1016/j.bmc.2010.10.009
- P. Singh, R. Raj, V. Kumar, M.P. Mahajan, P.M.S. Bedi, T. Kaur and A.K. Saxena, Eur. J. Med. Chem., 47, 594 (2012); https://doi.org/10.1016/j.ejmech.2011.10.033
- R. Marik, M. Allu, R. Anchoori, V. Stearns, C.B. Umbricht and S. Khan, Cancer Biol. Ther., 11, 883 (2011); https://doi.org/10.4161/cbt.11.10.15184
- M. Nagamani, P. Jalapathi, B. Shankar, M. Neelamma and T.M. Krishna, Russ. J. Gen. Chem., 89, 998 (2019); https://doi.org/10.1134/S1070363219050207
References
N.G.V. Aher, S.N. Pore, N. Mishra, A. Kumar, P.K. Shukla, A. Sharma and M.K. Bhat, Bioorg. Med. Chem. Lett., 19, 759 (2009); https://doi.org/10.1016/j.bmcl.2008.12.026
X.L. Wang, K. Wan and C.H. Zhou, Eur. J. Med. Chem., 45, 4631 (2010); https://doi.org/10.1016/j.ejmech.2010.07.031
A. Kamal, N. Shankaraiah, V. Devaiah, K. Laxma Reddy, A. Juvekar, S. Sen, N. Kurian and S. Zingde, Bioorg. Med. Chem. Lett., 18, 1468 (2008); https://doi.org/10.1016/j.bmcl.2007.12.063
D.K. Kim, J. Kim and H.J. Park, Bioorg. Med. Chem. Lett., 14, 2401 (2004); https://doi.org/10.1016/j.bmcl.2004.03.024
O. Ciofu and T. Tolker-Nielsen, Front. Microbiol., 10, 913 (2019); https://doi.org/10.3389/fmicb.2019.00913
B.K. Singh, A.K. Yadav, B. Kumar, A. Gaikwad, S.K. Sinha, V. Chaturvedi and R.P. Tripathi, Carbohydr. Res., 343, 1153 (2008); https://doi.org/10.1016/j.carres.2008.02.013
P.V. Chavan, K.S. Pandit, U.V. Desai, M.A. Kulkarni and P.P. Wadgaonkar, RSC Adv., 4, 42137 (2014); https://doi.org/10.1039/C4RA05080K
H. Khalil, T. El Malah, A.I.A. El Maksoud, I. El Halfawy, A.A. El Rashedy and M. El Hefnawy, Front. Cell. Infect.Microbiol., 7, 304 (2017); https://doi.org/10.3389/fcimb.2017.00304
I.E. Glowacka, G. Andrei, D. Schols, R. Snoeck and D.G. Piotrowska, Molecules, 20, 18789 (2015); https://doi.org/10.3390/molecules201018789
H. Cheng, J. Wan, M.I. Lin, Y. Liu, X. Lu, J. Liu, Y. Xu, J. Chen, Z. Tu, Y.S.E. Cheng and K. Ding, J. Med. Chem., 55, 2144 (2012); https://doi.org/10.1021/jm2013503
M. Saeedi, M. Mohammadi Khanaposhtani, P. Pourrabia, N. Razzaghi, R. Ghadimi, S. Imanparast, M.A. Faramarzi, F. Bandarian, E.N. Esfahani, M. Safavi, H. Rastegar, B. Larijani, M. Mahdavi and T. Akbarzadeh, Bioorg. Chem., 83, 161 (2019); https://doi.org/10.1016/j.bioorg.2018.10.023
I. Mohammed, I.R. Kummetha, G. Singh, N. Sharova, G. Lichinchi, J. Dang, M. Stevenson and T.M. Rana, J. Med. Chem., 59, 7677 (2016); https://doi.org/10.1021/acs.jmedchem.6b00247
Z. Zhou, T. Liu, G. Wu, D. Kang, Z. Fu, Z. Wang, E. De Clercq, C. Pannecouque, P. Zhan and X. Liu, Org. Biomol. Chem., 17, 3202 (2019); https://doi.org/10.1039/C9OB00032A
X. Jiang, G. Wu, W.A. Zalloum, M.E. Meuser, A. Dick, L. Sun, C.H. Chen, D. Kang, L. Jing, R. Jia, S. Cocklin, K.-H. Lee, X. Liu and P. Zhan, RSC Adv., 9, 28961 (2019); https://doi.org/10.1039/C9RA05869A
F.C. da Silva, M.C.B.V. de Souza, I.I.P. Frugulhetti, H.C. Castro, S.L.O. Souza, T.M.L. de Souza, D.Q. Rodrigues, A.M.T. Souza, P.A. Abreu and F. Passamani, Eur. J. Med. Chem., 44, 373 (2009); https://doi.org/10.1016/j.ejmech.2008.02.047
F. Naaz, M.C. Preeti Pallavi, S. Shafi, N. Mulakayala, M. Shahar Yar and H.M. Sampath Kumar, Bioorg. Chem., 81, 1 (2018); https://doi.org/10.1016/j.bioorg.2018.07.029
S. Haider, M.S. Alam, H. Hamid, S. Shafi, A. Nargotra, P. Mahajan, S. Nazreen, A.M. Kalle, C. Kharbanda, Y. Ali, A. Alam and A.K. Panda, Eur. J. Med. Chem., 70, 579 (2013); https://doi.org/10.1016/j.ejmech.2013.10.032
F. Ahmadi, M.R. Ghayahbashi, M. Sharifzadeh, E. Alipoiur, S.N. Ostad, M. Vosooghi, H.R. Khademi and M. Amini, Med. Chem., 11, 69 (2014); https://doi.org/10.2174/1573406410666140613154507
N. Batra, V. Rajendran, D. Agarwal, I. Wadi, P.C. Ghosh, R.D. Gupta and M. Nath, Chemistry Select, 3, 9790 (2018); https://doi.org/10.1002/slct.201801905
E.O.J. Porta, I. Bofill Verdaguer, C. Perez, C. Banchio, M. Ferreira de Azevedo, A.M. Katzin and G.R. Labadie, MedChemComm, 10, 1599 (2019); https://doi.org/10.1039/C9MD00298G
L. Savegnago, M. Sacramento, L.M.P. Brod, M.G. Fronza, N. Seus, E.J. Lenardão, M.W. Paixão and D. Alves, RSC Advances, 6, 8021 (2016); https://doi.org/10.1039/C5RA22445D
T. Settypalli, V.R. Chunduri, A.K. Maddineni, N. Begari, R. Allagadda, P. Kotha and A.R. Chippada, New J. Chem., 43, 15435 (2019); https://doi.org/10.1039/C9NJ02580D
D.S. Kapkoti, S. Singh, S. Luqman and R.S. Bhakuni, New J. Chem., 42, 5978 (2018); https://doi.org/10.1039/C7NJ04271J
A. Singh, S.T. Saha, S. Perumal, M. Kaur and V. Kumar, ACS Omega, 3, 1263 (2018); https://doi.org/10.1021/acsomega.7b01755
D.-J. Fu, S.-Y. Zhang, Y.-C. Liu, X.-X. Yue, J.-J. Liu, J. Song, R.-H. Zhao, F. Li, H.-H. Sun, Y.-B. Zhang and H.-M. Liu, MedChemComm, 7, 1664 (2016); https://doi.org/10.1039/C6MD00169F
Z. Nowakowska, Eur. J. Med. Chem., 42, 125 (2007); https://doi.org/10.1016/j.ejmech.2006.09.019
T. Akihisa, H. Tokuda, D. Hasegawa, M. Ukiya, Y. Kimura, F. Enjo, T. Suzuki and H. Nishino, J. Nat. Prod., 69, 38 (2006); https://doi.org/10.1021/np058080d
K.L. Lahtchev, D.I. Batovska, P. Parushev, V.M. Ubiyvovk and A.A. Sibirny, Eur. J. Med. Chem., 43, 2220 (2008); https://doi.org/10.1016/j.ejmech.2007.12.027
D.K. Mahapatra, S.K. Bharti and V. Asati, Eur. J. Med. Chem., 98, 69 (2015); https://doi.org/10.1016/j.ejmech.2015.05.004
R. Kant, D. Kumar, D. Agarwal, R.D. Gupta, R. Tilak, S.K. Awasthi and A. Agarwal, Eur. J. Med. Chem., 113, 34 (2016); https://doi.org/10.1016/j.ejmech.2016.02.041
P. Yadav, K. Lal, L. Kumar, A. Kumar, A. Kumar, A.K. Paul and R. Kumar, Eur. J. Med. Chem., 155, 263 (2018); https://doi.org/10.1016/j.ejmech.2018.05.055
E.M. Guantai, K. Ncokazi, T.J. Egan, J. Gut, P.J. Rosenthal, P.J. Smith and K. Chibale, Bioorg. Med. Chem., 18, 8243 (2010); https://doi.org/10.1016/j.bmc.2010.10.009
P. Singh, R. Raj, V. Kumar, M.P. Mahajan, P.M.S. Bedi, T. Kaur and A.K. Saxena, Eur. J. Med. Chem., 47, 594 (2012); https://doi.org/10.1016/j.ejmech.2011.10.033
R. Marik, M. Allu, R. Anchoori, V. Stearns, C.B. Umbricht and S. Khan, Cancer Biol. Ther., 11, 883 (2011); https://doi.org/10.4161/cbt.11.10.15184
M. Nagamani, P. Jalapathi, B. Shankar, M. Neelamma and T.M. Krishna, Russ. J. Gen. Chem., 89, 998 (2019); https://doi.org/10.1134/S1070363219050207