Copyright (c) 2025 A. KISHORE BABU, K. SELVARAJU, G.K. AYYADURAI, Jayaprakash Rajendran
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis, Characterization, Theoretical and Antimicrobial Studies of Substituted Isoxazoline Derivatives
Corresponding Author(s) : K. Selvaraju
Asian Journal of Chemistry,
Vol. 37 No. 6 (2025): Vol 37 Issue 6, 2025
Abstract
This research focuses on the design of new compounds and their biological applications to address various medical issues and pandemics caused by diverse microorganisms. In this work, two novel isoxazoline derivatives containing chlorine and methoxy groups at the para position were synthesized, characterized by various known techniques and QSAR properties were calculated using Osiris and docking against the protein targets such as 1HNJ, 1KZN and 1T15. The theoretical outcomes are compared with the experimental antimicrobial investigations on B. subtilis, E. coli, S. aureus, K. pneumoniae, C. albicans and A. niger using agar well-diffusion method. The derived derivatives exhibited good results and showed good coincidence with theoretical results. Out of two target compounds, activating methoxy group substituted isoxazoline compound showed better result against bacterial strains (12-16 mm), whereas deactivating chlorine group substituted compound revealed the good result (12-15 mm) against fungus strains.
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- G. Mancuso, A. Midiri, E. Gerace and C. Biondo, Pathogens, 10, 1310 (2021); https://doi.org/10.3390/pathogens10101310
- G. Muteeb, M.T. Rehman, M. Shahwan and M. Aatif, Pharmaceuticals, 16, 1615 (2023); https://doi.org/10.3390/ph16111615
- J. Jampilek, Molecules, 24, 3839 (2019); https://doi.org/10.3390/molecules24213839
- M. Szumilak and A. Stanczak, Molecules, 24, 2271 (2019); https://doi.org/10.3390/molecules24122271
- N. Kerru, L. Gummidi, S. Maddila, K.K. Gangu and S.B. Jonnalagadda, Molecules, 25, 1909 (2020); https://doi.org/10.3390/molecules25081909
- T. Biswas, R.K. Mittal, V. Sharma, Kanupriya and I. Mishra, Med. Chem., 20, 369 (2024); https://doi.org/10.2174/0115734064278334231211054053
- G.C. Arya, K. Kaur and V. Jaitak, Eur. J. Med. Chem., 221, 113511 (2021); https://doi.org/10.1016/j.ejmech.2021.113511
- N.K. Kochetkov and S.D. Sokolov, Adv. Heterocycl. Chem., 2, 365 (1963); https://doi.org/10.1016/S0065-2725(08)60755-2
- B.A. Chalyk, K.V. Hrebeniuk, Y.V. Fil, K.S. Gavrilenko, A.B. Rozhenko, B.V. Vashchenko, O.V. Borysov, A.V. Biitseva, P.S. Lebed, I. Bakanovych, Y.S. Moroz and O.O. Grygorenko, J. Org. Chem., 84, 15877 (2019); https://doi.org/10.1021/acs.joc.9b02264
- G.J. Martis and S.L. Gaonkar, RSC Adv., 15, 8213 (2025); https://doi.org/10.1039/d4ra08339c
- N. Agrawal and P. Mishra, Med. Chem. Res., 27, 1309 (2018); https://doi.org/10.1007/s00044-018-2152-6
- M. Zimecki, U. Bachor and M. Maczyñski, Molecules, 23, 2724 (2018); https://doi.org/10.3390/molecules23102724
- A. Shaik, R.R. Bhandare, K. Palleapati, S. Nissankararao, V. Kancharlapalli and S. Shaik, Molecules, 25, 1047 (2020); https://doi.org/10.3390/molecules25051047
- A. Sysak and B. Obmiñska-Mrukowicz, Eur. J. Med. Chem., 137, 292 (2017); https://doi.org/10.1016/j.ejmech.2017.06.002
- J. Zhu, J. Mo, H.Z. Lin, Y. Chen and H.P. Sun, Bioorg. Med. Chem., 26, 3065 (2018); https://doi.org/10.1016/j.bmc.2018.05.013
- N. Barghady, S.A. Assou, M. Er-Rajy, K. Boujdi, A. Arzine, Y. Rhazi, B. Tüzün, A. Nakkabi, M. Chalkha, M. El Hassouni, A. Kabra, M.M. Alanazi, A. Baouid and M. El Yazidi, Open Chem., 22, 20240109 (2024); https://doi.org/10.1515/chem-2024-0109
- G.K. Ayyadurai, R. Jayaprakash, A. Shajahan and S. Rathika, J. Biomol. Struct. Dyn., 43, 2864 (2025); https://doi.org/10.1080/07391102.2023.2294383
- B. Vasilev and M. Atanasova, Appl. Sci., 15, 1206 (2025); https://doi.org/10.3390/app15031206
- K. Vashisht, P. Sethi, A. Bansal, T. Singh, R. Kumar, H.S. Tuli, S. Saini and J. Eur, Clin. Exp. Med., 22, 376 (2024); https://doi.org/10.15584/ejcem.2024.2.25
- A. Arzine, H. Hadni, K. Boujdi, K. Chebbac, N. Barghady, Y. Rhazi, M. Chalkha, A. Nakkabi, K. Chkirate, J.T. Mague, S.M.A. Kawsar, G. Al Houari, M. M. Alanazi and M. El Yazidi, Molecules, 29, 3366 (2024); https://doi.org/10.3390/molecules29143366
- A.P. Subramanian, R. Samiyappan, B. Anitha, G.K. Ayyadurai and J. Rajendran, J. Biomed Pharmacol., 17, 2535 (2024); https://doi.org/10.13005/bpj/3046
- H. Aziz, A. Mahmood, S. Zaib, A. Saeed, H.R. El-Seedi, J. Pelletier, J. Sévigny and J. Iqbal, J. Biomol. Struct. Dyn., 39, 6140 (2020); https://doi.org/10.1080/07391102.2020.1802336
- S. Bano, M.S. Alam, K. Javed, M. Dudeja, A.K. Das and A. Dhulap, Eur. J. Med. Chem., 95, 96 (2015); https://doi.org/10.1016/j.ejmech.2015.03.031
- S.S. Ragab, M. Abdelraof, A.A. Elrashedy and A.M.K. Sweed, J. Mol. Struct., 1278, 134912 (2023); https://doi.org/10.1016/j.molstruc.2023.134912
- A. Saleem, U. Farooq, S.M. Bukhari, S. Khan, A. Zaidi, T.A. Wani, A.J. Shaikh, R. Sarwar, S. Mahmud, M. Israr, F.A. Khan and S.A. Shahzad, ACS Omega, 7, 30359 (2022); https://doi.org/10.1021/acsomega.2c03600
- N. Puttaswamy, G.S. Pavan Kumar, M. Al-Ghorbani, V. Vigneshwaran, B.T. Prabhakar and S.A. Khanum, Eur. J. Med. Chem., 114, 153 (2016); https://doi.org/10.1016/j.ejmech.2016.02.052
- G. Ayyadurai, S. Rathika, S. Sumathi and R. Jayaprakash, Asian J. Chem., 36, 1601 (2024); https://doi.org/10.14233/ajchem.2024.31757
- Sonu, K. Yt, G.K. Gautam, A.K. Mishra, B.R. Parveen, A. Kumar, M. Singh and H. Singh, Heliyon, 10, 1 (2024); https://doi.org/10.1016/j.heliyon.2024.e40300
- E. Wagner, K. Al-Kadasi, M. Zimecki and W. Sawka-Dobrowolska, Eur. J. Med. Chem., 43, 2498 (2008); https://doi.org/10.1016/j.ejmech.2008.01.035
- P.C. Shyma, B. Kalluraya, A.M. Vijesh, S.K. Peethambar and T. Arulmoli, Int. J. Res. Pharm. Chem., 4, 1009 (2014).
- M. Kratky and J. Vinsova, Curr. Pharm. Des., 17, 3494 (2011); https://doi.org/10.2174/138161211798194521
- C. Ramalingan, S. Balasubramanian, S. Kabilan and M. Vasudevan, Eur. J. Med. Chem., 39, 527 (2004); https://doi.org/10.1016/j.ejmech.2004.02.005
References
G. Mancuso, A. Midiri, E. Gerace and C. Biondo, Pathogens, 10, 1310 (2021); https://doi.org/10.3390/pathogens10101310
G. Muteeb, M.T. Rehman, M. Shahwan and M. Aatif, Pharmaceuticals, 16, 1615 (2023); https://doi.org/10.3390/ph16111615
J. Jampilek, Molecules, 24, 3839 (2019); https://doi.org/10.3390/molecules24213839
M. Szumilak and A. Stanczak, Molecules, 24, 2271 (2019); https://doi.org/10.3390/molecules24122271
N. Kerru, L. Gummidi, S. Maddila, K.K. Gangu and S.B. Jonnalagadda, Molecules, 25, 1909 (2020); https://doi.org/10.3390/molecules25081909
T. Biswas, R.K. Mittal, V. Sharma, Kanupriya and I. Mishra, Med. Chem., 20, 369 (2024); https://doi.org/10.2174/0115734064278334231211054053
G.C. Arya, K. Kaur and V. Jaitak, Eur. J. Med. Chem., 221, 113511 (2021); https://doi.org/10.1016/j.ejmech.2021.113511
N.K. Kochetkov and S.D. Sokolov, Adv. Heterocycl. Chem., 2, 365 (1963); https://doi.org/10.1016/S0065-2725(08)60755-2
B.A. Chalyk, K.V. Hrebeniuk, Y.V. Fil, K.S. Gavrilenko, A.B. Rozhenko, B.V. Vashchenko, O.V. Borysov, A.V. Biitseva, P.S. Lebed, I. Bakanovych, Y.S. Moroz and O.O. Grygorenko, J. Org. Chem., 84, 15877 (2019); https://doi.org/10.1021/acs.joc.9b02264
G.J. Martis and S.L. Gaonkar, RSC Adv., 15, 8213 (2025); https://doi.org/10.1039/d4ra08339c
N. Agrawal and P. Mishra, Med. Chem. Res., 27, 1309 (2018); https://doi.org/10.1007/s00044-018-2152-6
M. Zimecki, U. Bachor and M. Maczyñski, Molecules, 23, 2724 (2018); https://doi.org/10.3390/molecules23102724
A. Shaik, R.R. Bhandare, K. Palleapati, S. Nissankararao, V. Kancharlapalli and S. Shaik, Molecules, 25, 1047 (2020); https://doi.org/10.3390/molecules25051047
A. Sysak and B. Obmiñska-Mrukowicz, Eur. J. Med. Chem., 137, 292 (2017); https://doi.org/10.1016/j.ejmech.2017.06.002
J. Zhu, J. Mo, H.Z. Lin, Y. Chen and H.P. Sun, Bioorg. Med. Chem., 26, 3065 (2018); https://doi.org/10.1016/j.bmc.2018.05.013
N. Barghady, S.A. Assou, M. Er-Rajy, K. Boujdi, A. Arzine, Y. Rhazi, B. Tüzün, A. Nakkabi, M. Chalkha, M. El Hassouni, A. Kabra, M.M. Alanazi, A. Baouid and M. El Yazidi, Open Chem., 22, 20240109 (2024); https://doi.org/10.1515/chem-2024-0109
G.K. Ayyadurai, R. Jayaprakash, A. Shajahan and S. Rathika, J. Biomol. Struct. Dyn., 43, 2864 (2025); https://doi.org/10.1080/07391102.2023.2294383
B. Vasilev and M. Atanasova, Appl. Sci., 15, 1206 (2025); https://doi.org/10.3390/app15031206
K. Vashisht, P. Sethi, A. Bansal, T. Singh, R. Kumar, H.S. Tuli, S. Saini and J. Eur, Clin. Exp. Med., 22, 376 (2024); https://doi.org/10.15584/ejcem.2024.2.25
A. Arzine, H. Hadni, K. Boujdi, K. Chebbac, N. Barghady, Y. Rhazi, M. Chalkha, A. Nakkabi, K. Chkirate, J.T. Mague, S.M.A. Kawsar, G. Al Houari, M. M. Alanazi and M. El Yazidi, Molecules, 29, 3366 (2024); https://doi.org/10.3390/molecules29143366
A.P. Subramanian, R. Samiyappan, B. Anitha, G.K. Ayyadurai and J. Rajendran, J. Biomed Pharmacol., 17, 2535 (2024); https://doi.org/10.13005/bpj/3046
H. Aziz, A. Mahmood, S. Zaib, A. Saeed, H.R. El-Seedi, J. Pelletier, J. Sévigny and J. Iqbal, J. Biomol. Struct. Dyn., 39, 6140 (2020); https://doi.org/10.1080/07391102.2020.1802336
S. Bano, M.S. Alam, K. Javed, M. Dudeja, A.K. Das and A. Dhulap, Eur. J. Med. Chem., 95, 96 (2015); https://doi.org/10.1016/j.ejmech.2015.03.031
S.S. Ragab, M. Abdelraof, A.A. Elrashedy and A.M.K. Sweed, J. Mol. Struct., 1278, 134912 (2023); https://doi.org/10.1016/j.molstruc.2023.134912
A. Saleem, U. Farooq, S.M. Bukhari, S. Khan, A. Zaidi, T.A. Wani, A.J. Shaikh, R. Sarwar, S. Mahmud, M. Israr, F.A. Khan and S.A. Shahzad, ACS Omega, 7, 30359 (2022); https://doi.org/10.1021/acsomega.2c03600
N. Puttaswamy, G.S. Pavan Kumar, M. Al-Ghorbani, V. Vigneshwaran, B.T. Prabhakar and S.A. Khanum, Eur. J. Med. Chem., 114, 153 (2016); https://doi.org/10.1016/j.ejmech.2016.02.052
G. Ayyadurai, S. Rathika, S. Sumathi and R. Jayaprakash, Asian J. Chem., 36, 1601 (2024); https://doi.org/10.14233/ajchem.2024.31757
Sonu, K. Yt, G.K. Gautam, A.K. Mishra, B.R. Parveen, A. Kumar, M. Singh and H. Singh, Heliyon, 10, 1 (2024); https://doi.org/10.1016/j.heliyon.2024.e40300
E. Wagner, K. Al-Kadasi, M. Zimecki and W. Sawka-Dobrowolska, Eur. J. Med. Chem., 43, 2498 (2008); https://doi.org/10.1016/j.ejmech.2008.01.035
P.C. Shyma, B. Kalluraya, A.M. Vijesh, S.K. Peethambar and T. Arulmoli, Int. J. Res. Pharm. Chem., 4, 1009 (2014).
M. Kratky and J. Vinsova, Curr. Pharm. Des., 17, 3494 (2011); https://doi.org/10.2174/138161211798194521
C. Ramalingan, S. Balasubramanian, S. Kabilan and M. Vasudevan, Eur. J. Med. Chem., 39, 527 (2004); https://doi.org/10.1016/j.ejmech.2004.02.005
