Synthesis, structural identification and biological potencies of quinolinium sulfonamide ionic liquids
Abstract
Members of the quinoline family include several alkaloids. Alkaloids are found in foods and beverages that humans consume daily, as well as in various stimulants. Among many other activities, they act against inflammation, cancer, bacteria, fungi and pain. Modifications of the alkyl chain after N-alkylation can alter the physicochemical properties and affect its multifunctional properties. This article describes the preparation and structural identification of five quinolinium sulfonamide ionic liquids that differ in N-alkylation functional group and chain length. Functional group and alkyl chain length in the N-alkylation of ionic liquids of quinolinium sulfonamide ionic liquids significantly affected the antioxidant activity and C-1 showed the highest antioxidant activity with the lowest IC50 of 20.56. Variation of substituents in the N-alkylation of ionic liquids of quinolinium sulfonamide also significantly affected its antibacterial and antifungus activity, with C-1 exhibiting the greatest activity. In addition, experimental results indicate that quinolinium sulfonamide ionic liquids significantly prolong the prothrombin time (PT) of normal human plasma.
Keywords:
Quinolinium ionic liquids, Sulfonamide functional group, Antioxidant Antibacterial, Antifungal and Anticoagulant activity.DOI
https://doi.org/10.25004/IJPSDR.2023.150315References
Sudhalakshmi J, Rajathi K. Data on creation and description of mono and dicationic bi-functionalized ionic liquids derived from aldehydic functionalized imidazolium ionic liquids. Chemical Data Collections 2023; 43: 100973. https://doi.org/10.1016/j.cdc.2022.100973
Smiglak M, Pringle JM, Lu X, Han L, Zhang S, Gao H, MacFarlane DR, Rogers RD. Ionic liquids for energy, materials, and medicine. Chem. Commun. 2014; 50: 9228-9250. https://doi.org/10.1039/C4CC2021A
Khupse ND, Kumar A. Ionic liquids: New materials with wide applications. Indian J. Chem. 2010; 49A: 635-648. https://nopr.niscpr.res.in/bitstream/123456789/9662/1/IJCA%2049A%2805-06%29%20635-648.pdf
Devaki SJ, Sasi R. Ionic Liquids/Ionic Liquid Crystals for Safe and Sustainable Energy Storage Systems. Progress and Developments in Ionic Liquids 2017; DOI: 10.5772/65888.
Xu W, Wang T, Cheng N, Hu Q, Bi Y, Gong Y, Yu L. Experimental and DFT studies on the aggregation behavior of imidazoliumbased surface-active ionic liquids with aromatic counter ions in aqueous solution. Langmuir 2015; 31(4): 1272-1282. https://doi.org/10.1021/la503884v
Kobayashi D, Fujita K, Nakamura N, Ohno H. A simple recovery process for biodegradable plastics accumulated in cyanobacteria treated with ionic liquids. Appl. Microbiol. Biotechnol. 2015; 99: 1647-1653. DOI:10.1007/s00253-014-6234-1
Rodrigues ASMC, Rocha MAA, Almeida HFD, Neves CMSS, Lopesda-Silva JA, Freire MG, Coutinho JAP, Santos LMNBF. Effect of the methylation and N−H acidic group on the physicochemical properties of imidazolium-based ionic liquids. J. Phys. Chem. B. 2015; 119: 8781-8792. https://doi.org/10.1021/acs.jpcb.5b05354
Wang M, Pan X, Chen J, Dai S. Regulating the mesogenic properties of imidazolium salts by modifying N3-substituents. Sci. China Chem. 2015; 58(12): 1884-1890. doi: 10.1007/s11426-015-5390-1
Supuran CT, Casini A, Scozzafava A. Protease inhibitors of the sulfonamide type: anticancer, antiinflammatory, and antiviral agents. Med. Res. Rev. 2003; 23(5): 535-558. doi: 10.1002/med.10047
Ovung A, Bhattacharyya J. Sulfonamide drugs: structure, antibacterial property, toxicity, and biophysical interactions. Biophysical Reviews 2021; 13(2): 259-272. https://doi.org/10.1007%2Fs12551-021-00795-9
Li N, Wang Y, Li W, Li H, Yang L, Wang J, Mahdy HA, Mehany ABM, Jaiash DA, Santali EY, Eissa IH. Screening of Some Sulfonamide and Sulfonylurea Derivatives as Anti-Alzheimer’s Agents Targeting BACE1 and PPARγ. Journal of Chemistry 2020. https://doi.org/10.1155/2020/1631243
Owa T, Nagasu T. Novel sulphonamide derivatives for the treatment of cancer. Expert Opinion on Therapeutic Patents 2000; 10(11): 1725-1740. https://doi.org/10.1517/13543776.10.11.1725
Ozdemir UO, Guvenç P, Sahin E, Hamurcu F. Synthesis, characterization and antibacterial activity of new sulfonamide derivatives and their nickel (II), cobalt (II) complexes. Inorganica Chimica Acta 2009; 362(8): 2613-2618. https://doi.org/10.1016/j.ica.2008.11.029
Askar FW, Aldhalf YA, Jinzeel NA. Synthesis and Biological Evaluation of New Sulfonamide Derivatives. International Journal of Chemical Science 2007; 15(3): 173. https://www.tsijournals.com/articles/synthesis-and-biological-evaluation-of-new-sulfonamidederivatives-13360.html
Siddiqui N, Arshad MF, Kan SA, Ahsan W. Sulfonamide derivatives of thiazolidin-4-ones with anticonvulsant activity against two seizure models: synthesis and pharmacological evaluation. Journal of Enzyme Inhibition and Medicinal Chemistry 2010; 25(4): 485-491. doi: 10.3109/14756360903282833
Kumar N, Khanna A, Kaur K, Kaur H, Sharma A, Singh Bedi PM. Quinoline derivatives volunteering against antimicrobial resistance: rational approaches, design strategies, structure activity relationship and mechanistic insights. Mol. Divers 2022. https://doi.org/10.1007/s11030-022-10537-y
Manoj Kumar M, Bhupender S, Chhikara, Parang K, Anil Kumar. Ionic Liquid-Supported Synthesis of Sulfonamides and Carboxamides. ACS Comb. Sci. 2012; 14: 60-65. https://doi.org/10.1021/co200149m
Ajani OO, Iyaye KT, Ademosun OT. Recent advances in chemistry and therapeutic potential of functionalized quinoline motifs– a review, RSC Adv. 2022; 12: 18594-18614. https://doi.org/10.1039/D2RA02896D
Snehi V, Pathak D. Synthesis, Characterization and Biological Evaluation of Novel Isoxazolo [5,4-b] Quinolines as Potent Antimicrobial Agents. International Journal of Pharmaceutical Sciences and Drug Research 2022; 14(6): 725-733. https://doi.org/10.25004/IJPSDR.2022.140609
Okolo EN, Ugwu DI, Ezema BE, Ndefo JC, Eze FU, Ezema CG, Ezugwu JA, Ujam OT. New chalcone derivatives as potential antimicrobial and antioxidant agent. Scientific Reports 2021; 11: 21781. https://doi.org/10.1038/s41598-021-01292-5
Venkatesh T, Bodke YD, Kenchappa R, Eilkar S. Synthesis, Antimicrobial and Antioxidant Activity of Chalcone Derivatives Containing Thiobarbitone Nucleus. Med. Chem. 2016; 6(7): 440-448. DOI: 10.4172/2161-0444.1000383
Santosh R, Selvam MK, Kanekar SU, Nagaraja GK. Synthesis, Characterization, Antibacterial and Antioxidant Studies of Some Heterocyclic Compounds from Triazole-Linked Chalcone Derivatives. ChemistrySelect 2018; 3: 6338-6343. https://doi.org/10.1002/slct.201800905
Mirani Nezhad S, NazarzadehZare E, Davarpanah A, Pourmousavi SA, Ashrafizadeh M, Kumar AP. Ionic Liquid-Assisted Fabrication of Bioactive Heterogeneous Magnetic Nanocatalyst with Antioxidant and Antibacterial Activities for the Synthesis of Poly hydro quinoline Derivatives. Molecules 2022; 27(5): 1748. https://doi.org/10.3390/molecules27051748
Su PW, Yang CH, Yang JF, Su PY, Chuang LY. Antibacterial Activities and Antibacterial Mechanism of Polygonum cuspidatum extracts against Nosocomial Drug-Resistant Pathogens. Molecules 2015; 20(6): 11119-11130. https://doi.org/10.3390/molecules200611119
Burman S, Bhattacharya K, Mukherjee D, Chandra G. Antibacterial efficacy of leaf extracts of Combretum album Pers. against some pathogenic bacteria. BMC Complementary and Alternative Medicine 2018; 18: 213-220. https://doi.org/10.1186/s12906-018-2271-0
Atef NM, Shanab SM, Negm SI, Abbas YA. Evaluation of antimicrobial activity of some plant extracts against antibiotic susceptible and resistant bacterial strains causing wound infection. Bulletin of the National Research Centre 2019; 43:144-156. https://doi.org/10.1186/s42269-019-0184-9
Foudah AI, Alam A, Soliman GA, Salkini MA, Ibnouf Ahmed EO, Yusufoglu HS. Pharmacognostical, Antibacterial and Antioxidant Studies of Aerial Parts of Pulicaria somalensis (Family: Asteraceae). Asian J. Biol.Sci. 2016; 9(1-2): 19-26. ht tps://scialert.net/abstract/?doi=ajbs.2016.19.26
Ashokan D, Rajathi K. A green Approach for Synthesis of Pyridinium Sulfonamide Ionic Liquids: Characterization and Their Biological Activities. Chemistry Africa 2023. https://doi.org/10.1007/s42250-023-00653-z
Hamlaoui I, Bencheraiet R, Bensegueni R, Bencharif M. Experimental and theoretical study on DPPH radical scavenging mechanism of some chalcone quinoline derivatives. Journal of molecular structure 2018; 1156: 385-389. https://doi.org/10.1016/j.molstruc.2017.11.118
Kim J, Yub H, Yang E, Choi Y, Chang PS. Effects of alkyl chain length on the interfacial, antibacterial, and antioxidative properties of erythorbyl fatty acid esters. LWT-Food science and Technology 2023; 174: 1144. https://doi.org/10.1016/j.lwt.2022.114421
Published

