Copyright (c) 2024 Kumar Rajathi
This work is licensed under a Creative Commons Attribution 4.0 International License.
Novel Unsymmetrical Dicationic Pyrrolidinium Ionic Liquids: Synthesis, Characterization and Antimicrobial Activities
Corresponding Author(s) : K. Rajathi
Asian Journal of Chemistry,
Vol. 36 No. 7 (2024): Vol 36 Issue 7, 2024
Abstract
Dicationic ionic liquids (DILs) have sparked a lot of attention due to their high melting point, better solubility, thermal stability and facilitated the creation of molecules with precise functions and application requirements. Dicationic ionic liquids have garnered significant attention in the field of green synthesis media due to their diverse cationic groups. In this work, four environmental friendly unsymmetrical dicationic room temperature ionic liquids with different cationic were synthesized by a simple neutralization process. The structure of the newly synthesized DILs was confirmed by FTIR, 1H NMR, 13C NMR, elemental and ESI-HRMS spectral analyses. All the synthesized DILs were also screened for antifungal, anti-inflammatory and antioxidant activities. When compared the microbial activities of DILs of different cations, the results showed that all the synthesized DILs were effective against Candida albicans fungi and had good scavenging activity in DPPH and against protein denaturation with their respective standards. Because of their sulphonic acid and hydroxyl groups in DIL-III and D-IV were the most promising candidates for antifungal, anti-inflammatory and antioxidant properties.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- B.M. Godajdar, A.R. Kiasat and M.M. Hashemi, J. Mol. Liq., 183, 14 (2013); https://doi.org/10.1016/j.molliq.2013.03.022
- N. Medjahed, M. Debdab, B. Haddad, E. Belarbi, Z. Kibou, A. Berrichi and N. Choukchou-Braham, Chem. Proc., 3, 80 (2020); https://doi.org/10.3390/ecsoc-24-08389
- M. Messali, Z. Moussa, A.Y. Alzahrani, M.Y. El-Naggar, A.S. El-Douhaibi, Z.M. Judeh and B. Hammouti, Chemosphere, 91, 1627 (2013); https://doi.org/10.1016/j.chemosphere.2012.12.062
- T.B.V. Dinis, F.A. e Silva, F. Sousa and M.G. Freire, Materials, 14, 6231 (2021); https://doi.org/10.3390/ma14216231
- M. Zabihzadeh, A. Omidi, F. Shirini, H. Tajik and M.S.N. Langarudi, J. Mol. Struct., 1206, 127730 (2020); https://doi.org/10.1016/j.molstruc.2020.127730
- P.K. Bhowmik, J.J. Koh, D. King, H. Han, B. Heinrich, B. Donnio, D. Zaton and A. Martinez-Felipe, J. Mol. Liq., 341, 117311 (2021); https://doi.org/10.1016/j.molliq.2021.117311
- M. Talebi, R.A. Patil and D.W. Armstrong, J. Mol. Liq., 256, 247 (2018); https://doi.org/10.1016/j.molliq.2018.02.016
- N. Iwai, K. Nakayama and T. Kitazume, Bioorg. Med. Chem. Lett., 21, 1728 (2011); https://doi.org/10.1016/j.bmcl.2011.01.081
- P. Ganapathi, K. Ganesan, M. Dharmasivam, M.M. Alam and A. Mohammed, ACS Omega, 7, 44458 (2022); https://doi.org/10.1021/acsomega.2c06833
- D. Bains, G. Singh, N. Kaur and N. Singh, ACS Appl. Bio Mater., 3, 4962 (2020); https://doi.org/10.1021/acsabm.0c00492
- S.J.L.P. Perez, J.E.C. Atayde Jr. and S.D. Arco, J. Chin. Chem. Soc., 67, 1270 (2020); https://doi.org/10.1002/jccs.201900366
- M. Benkova, O. Soukup and J. Marck, J. Appl. Microbiol., 129, 806 (2020); https://doi.org/10.1111/jam.14704
- D. Vijayaraj, J. Anarkali, K. Rajathi and S. Sridhar, Nano Biomed. Eng., 4, 95 (2012); https://doi.org/10.5101/nbe.v4i2.p95-98
- D. Ashokan and K. Rajathi, Chem. Africa, 6, 2495 (2023); https://doi.org/10.1007/s42250-023-00653-z
- V. Sharma, Himanshu and D.N.S. Gautam, Asian J. Pharm. Pharmacol., 4, 179 (2018); https://doi.org/10.31024/ajpp.2018.4.2.13
- S. Gholivand, O. Lasekan, C.P. Tan, F. Abas and L.S. Wei, Food Chem., 224, 365 (2017); https://doi.org/10.1016/j.foodchem.2016.12.075
- M. Demurtas, V. Onnis, P. Zucca, A. Rescigno, J.I. Lachowicz, L. De Villiers-Engelbrecht, M. Nieddu, G. Ennas, A. Scano, F. Mocci and F. Cesare-Marincola, ACS Sustain. Chem. Eng., 9, 2975 (2021); https://doi.org/10.1021/acssuschemeng.1c00090
- A. Patel, A. Patel, A. Patel and N.M. Patel, Pharmacognosy Res., 2, 152 (2010); https://doi.org/10.4103/0974-8490.65509
- O.O. Ajani, K.T. Iyaye and O.T. Ademosun, RSC Adv., 12, 18594 (2022); https://doi.org/10.1039/D2RA02896D
- N.R. Bhalodia and V. Shukla, J. Adv. Pharm. Technol. Res., 2, 104 (2011); https://doi.org/10.4103/2231-4040.82956
- C.N. Pace, H. Fu, K. Lee Fryar, J. Landua, S.R. Trevino, D. Schell, R.L. Thurlkill, S. Imura, J.M. Scholtz, K. Gajiwala, J. Sevcik, L. Urbanikova, J.K. Myers, K. Takano, E.J. Hebert, B.A. Shirley and G.R. Grimsley, Protein Sci., 23, 652 (2014); https://doi.org/10.1002/pro.2449
- K. Czerniak and F. Walkiewicz, New J. Chem., 41, 530 (2017); https://doi.org/10.1039/C6NJ02428A
References
B.M. Godajdar, A.R. Kiasat and M.M. Hashemi, J. Mol. Liq., 183, 14 (2013); https://doi.org/10.1016/j.molliq.2013.03.022
N. Medjahed, M. Debdab, B. Haddad, E. Belarbi, Z. Kibou, A. Berrichi and N. Choukchou-Braham, Chem. Proc., 3, 80 (2020); https://doi.org/10.3390/ecsoc-24-08389
M. Messali, Z. Moussa, A.Y. Alzahrani, M.Y. El-Naggar, A.S. El-Douhaibi, Z.M. Judeh and B. Hammouti, Chemosphere, 91, 1627 (2013); https://doi.org/10.1016/j.chemosphere.2012.12.062
T.B.V. Dinis, F.A. e Silva, F. Sousa and M.G. Freire, Materials, 14, 6231 (2021); https://doi.org/10.3390/ma14216231
M. Zabihzadeh, A. Omidi, F. Shirini, H. Tajik and M.S.N. Langarudi, J. Mol. Struct., 1206, 127730 (2020); https://doi.org/10.1016/j.molstruc.2020.127730
P.K. Bhowmik, J.J. Koh, D. King, H. Han, B. Heinrich, B. Donnio, D. Zaton and A. Martinez-Felipe, J. Mol. Liq., 341, 117311 (2021); https://doi.org/10.1016/j.molliq.2021.117311
M. Talebi, R.A. Patil and D.W. Armstrong, J. Mol. Liq., 256, 247 (2018); https://doi.org/10.1016/j.molliq.2018.02.016
N. Iwai, K. Nakayama and T. Kitazume, Bioorg. Med. Chem. Lett., 21, 1728 (2011); https://doi.org/10.1016/j.bmcl.2011.01.081
P. Ganapathi, K. Ganesan, M. Dharmasivam, M.M. Alam and A. Mohammed, ACS Omega, 7, 44458 (2022); https://doi.org/10.1021/acsomega.2c06833
D. Bains, G. Singh, N. Kaur and N. Singh, ACS Appl. Bio Mater., 3, 4962 (2020); https://doi.org/10.1021/acsabm.0c00492
S.J.L.P. Perez, J.E.C. Atayde Jr. and S.D. Arco, J. Chin. Chem. Soc., 67, 1270 (2020); https://doi.org/10.1002/jccs.201900366
M. Benkova, O. Soukup and J. Marck, J. Appl. Microbiol., 129, 806 (2020); https://doi.org/10.1111/jam.14704
D. Vijayaraj, J. Anarkali, K. Rajathi and S. Sridhar, Nano Biomed. Eng., 4, 95 (2012); https://doi.org/10.5101/nbe.v4i2.p95-98
D. Ashokan and K. Rajathi, Chem. Africa, 6, 2495 (2023); https://doi.org/10.1007/s42250-023-00653-z
V. Sharma, Himanshu and D.N.S. Gautam, Asian J. Pharm. Pharmacol., 4, 179 (2018); https://doi.org/10.31024/ajpp.2018.4.2.13
S. Gholivand, O. Lasekan, C.P. Tan, F. Abas and L.S. Wei, Food Chem., 224, 365 (2017); https://doi.org/10.1016/j.foodchem.2016.12.075
M. Demurtas, V. Onnis, P. Zucca, A. Rescigno, J.I. Lachowicz, L. De Villiers-Engelbrecht, M. Nieddu, G. Ennas, A. Scano, F. Mocci and F. Cesare-Marincola, ACS Sustain. Chem. Eng., 9, 2975 (2021); https://doi.org/10.1021/acssuschemeng.1c00090
A. Patel, A. Patel, A. Patel and N.M. Patel, Pharmacognosy Res., 2, 152 (2010); https://doi.org/10.4103/0974-8490.65509
O.O. Ajani, K.T. Iyaye and O.T. Ademosun, RSC Adv., 12, 18594 (2022); https://doi.org/10.1039/D2RA02896D
N.R. Bhalodia and V. Shukla, J. Adv. Pharm. Technol. Res., 2, 104 (2011); https://doi.org/10.4103/2231-4040.82956
C.N. Pace, H. Fu, K. Lee Fryar, J. Landua, S.R. Trevino, D. Schell, R.L. Thurlkill, S. Imura, J.M. Scholtz, K. Gajiwala, J. Sevcik, L. Urbanikova, J.K. Myers, K. Takano, E.J. Hebert, B.A. Shirley and G.R. Grimsley, Protein Sci., 23, 652 (2014); https://doi.org/10.1002/pro.2449
K. Czerniak and F. Walkiewicz, New J. Chem., 41, 530 (2017); https://doi.org/10.1039/C6NJ02428A