Abstract
An efficient green ultrasound-assisted procedure for the preparation of five new functionalized 1-alkyl-3-butylimidazolium ionic liquids (ILs) 2–6 is described. Their structures were characterized by FT-IR, 1H NMR, and 13C NMR spectroscopy and mass spectrometry. The newly synthesized compounds were screened for their antimicrobial and anticancer activities. The former revealed that the ILs exhibited promising activity compared with standard drugs. Moreover, IL 4 was found to be a very promising antiproliferative agent against the human hepatocellular carcinoma (HEPG2), human breast adenocarcinoma (MCF7), and colon carcinoma (HCT116) cell lines and consistently produced low IC50 values.
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References
Al-Ghamdi AF, Messali M, Ahmed SA (2011) Electrochemical studies of new pyridazinium-based ionic liquid and its determination in different detergents. J Mater Environ Sci 2:215–224
Anastas PT, Warner JC (1998) Green chemistry, theory and practice. Oxford University Press, Oxford
Atta-Ur-Rahman MI, Thomsen WJ (2001) Bioassay Technique for Drug Development. Harwood Academic, The Netherlands
Aupoix A, Pegot B, Vo-Thanh G (2010) Synthesis of imidazolium and pyridinium-based ionic liquids and application of 1-alkyl-3-methylimidazolium salts as pre-catalysts for the benzoin condensation using solvent-free and microwave activation. Tetrahedron 66:1352–1356
Balducci A, Bardi U, Caporali S, Mastragostino M, Soavi F (2004) Ionic liquids for hybrid supercapacitors. Electrochem Commun 6:566–570
Brennecke JF, Magin EJ (2001) Ionic liquids: innovative fluids for chemical processing. AIChE J 47:2384–2389
Carmichael H (2000) Making waves. Chem Br 36(1):36–37
Chohan ZH, Youssoufi MH, Jarrahpour A, Hadda TB (2010) Identification of inhibition:indolenyl sulphonamide derivatives. Eur J Med Chem 45:1189–1199
Cornellas A, Perez L, Comelles F, Ribosa I, Manresa A, Garcia MT (2011) Self-aggregation and antimicrobial activity of imidazolium and pyridinium based ionic liquids in aqueous solution. J Colloid Interface Sci 355:164–171
Davis JH Jr (2004) Task-specific ionic liquids. Chem Lett 33:1072–1077
De Souza RF, Padilha JC, Goncalves RS, Rault-Berthelot JL (2006) Dialkylammonium ionic liquids as electrolytes for hydrogen production from water electrolysis. Electrochem Commun 8:211–216
Deetlefs M, Seddon KR (2003) Improved preparations of ionic liquids using microwave irradiation. Green Chem 5:181–186
Endres F (2002) Ionic liquids: solvents for the electrodeposition of metals and semiconductors. Chem Phys Chem 3:144–154
Ertl P, Rohde B, Selzer P (2000) Fast calculation of molecular polar surface area (PSA) as a sum on fragment-based contributions and its application to the prediction of drug transport properties. J Med Chem 43:3714–3717
European Committee for Antimicrobial Susceptibility Testing (EUCAST) of the European Society of Clinical Microbiology and Infectious Diseases (ESCMID) (2000) Determination of minimum inhibitory concentrations (MICs) of antibacterial agents by agar dilution. Clin Microbiol Infect Suppl 509–515
Hadda TB, Fathi J, Chafchaouni I, Masand V, Charrouf Z, Chohan ZH, Jawarkar R, Fergoug T (2013a) Computational POM and 3D-QSAR evaluation of experimental in vitro HIV-1 integrase inhibition of amide-containing di-ketoacids. Med Chem Res 22:1456–1464
Hadda TB, Kerbal A, Bennani B, Al Houari G, Daoudi M, Leite ACL, Masand VH, Jawarkar RD, Charrouf Z (2013b) Molecular drug design, synthesis and pharmacophore site identification of spiroheterocyclic compounds: trypanosoma crusi inhibiting studies. Med Chem Res 22:57–69
Hadda TB, Ali MA, Masand V, Gharby S, Fergoug T, Warad I (2013c) Tautomeric origin of dual effects of N1-nicotinoyl-3-(4′-hydroxy-3′-methyl phenyl)-5-[(sub)phenyl]-2- pyrazolines on bacterial and viral strains: POM analyses as new efficient bioinformatics’ platform to predict and optimize bioactivity of drugs. Med Chem Res 22:1438–1449
Hossain MI, El-Harbawi M, Noaman YA, Bustam MAB, Alitheen NBM, Affandi NA, Hefter G, Yin CY (2011) Synthesis and anti-microbial activity of hydroxylammonium ionic liquids. Chemosphere 84:101–104
Ibrahim MAM, Messali M (2011) Ionic liquid [BMPy] Br as an effective additive during zinc electrodeposition from an aqueous sulfate bath. Prod Finish 76:14
Ibrahim MAM, Messali M, Moussa Z, Alzahrani AY, Alamry SN, Hammouti B (2011) Corrosion inhibition of carbon steel by imidazolium and pyridinium cations ionic liquids in acidic environment. Port Electrochim Acta 29:375–389
Kaushik NK, Attri P, Kaushik N, Choi EH (2012) Molecules 17:13727–13739
Kubisa P (2004) Application of ionic liquids as solvents for polymerization processes. Prog Polym Sci 29:3
Lin YF, Sun IW (1999) Electrodeposition of zinc from a Lewis acidic zinc chloride-1-ethyl-3-methylimidazolium chloride molten salt. Electrochim Acta 44:2771–2777
Liu J, Jiang G, Chi Y, Cai Y, Zhou Q, Hu J (2003) Use of ionic liquids for liquid-phase microextraction of polycyclic aromatic hydrocarbons. Anal Chem 21:5870–5876
Messali M (2011a) A green microwave-assisted synthesis, characterization and comparative study of new pyridazinium-based ionic liquids derivatives towards corrosion of mild steel in acidic environment. J Mater Environ Sci 2:174–185
Messali M (2011b) A facile and green microwave-assisted synthesis of new functionalized picolinium-based ionic liquids. Arab J Chem. doi: 10.1016/j.arabjc.2011.06.030
Messali M (2014) An efficient and green sonochemical synthesis of some new eco-friendly functionalized ionic liquids. Arab J Chem 7:63–70
Messali M, Ahmed SA (2011) A green microwave-assisted synthesis of new pyridazinium-based ionic liquids as an environmentally friendly alternative. Green Sustain Chem 1:70–75
Messali M, Asiri MAM (2013) A green ultrasound-assisted access to some new 1-benzyl-3-(4-phenoxybutyl) imidazolium-based ionic liquids derivatives—a potent agents inhibitors against corrosion of mild steel in acidic environment. J Mater Environ Sci 4(5):770–785
Messali M, Moussa Z, Alzahrani AY, El Naggar MY, ElDouhaibi AS, Hammouti B (2013) Synthesis, characterization, antimicrobial activity of new green-chemistry-friendly ionic liquids. Chemosphere 91:1627–1634
Namboodiri VV, Varma RS (2002) Solvent-free sonochemical preparation of ionic liquids. Org Lett 4:3161–3163
Oxley JD, Prozorov T, Suslick KS (2003) Sonochemistry and Sonoluminescence of room-temperature ionic liquids. J Am Chem Soc 125:11138–11139
Saadeh SM, Yasseen Z, Sharif FA, Abu Shawish HM (2009) New room temperature ionic liquids with interesting ecotoxicological and antimicrobial properties. Ecotoxicol Environ Saf 72:1805–1809
Seddon K (1998) Molten salt forum: proceedings of 5th international conference on molten salt chemistry and technology, 53, pp 5–6
Sheikh J, Hadda TB (2013) Antibacterial, antifungal and antioxidant activity of some new water-soluble b-diketones. Med Chem Res 22:964–975
Sheldon R (2001) Catalytic reactions in ionic liquids. Chem Commun 2001:2399–2407
Singh V, Kaur S, Sapehiyia V, Singh J, Kad GL (2005) Microwave accelerated preparation of [bmim][HSO4] ionic liquid: an acid catalyst for improved synthesis of coumarins. Catalysis Comm 6:57–60
Takahashi S, Koura N, Kohara S, Saboungi ML, Curtiss LA (1999) Technological and scientific issues of room-temperature molten salt. Plasmas Ions 2:91–105
Ue M, Takeda M, Toriumi A, Kominato A, Hagiwara R, Ito Y (2003) Application of low-viscosity ionic liquid to the electrolyte of double-layer capacitors. J Electrochem Soc 150:499–502
Wang P, Wenger B, Humphry-Baker R, Moser JE, Teuscher J, Kantlehner W, Mezger J, Stoyanov EV, Zakeeruddin SM, Gratzel MJ (2005) Charge separation and efficient light energy conversion in sensitized mesoscopic solar cells based on binary ionic liquids. J Am Chem Soc 127:6850–6856
Wang JH, Cheng DH, Du Chen XYZ, Fang ZL (2007) Direct extraction of double stranded DNA into ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate and its quantification. Anal Chem 79:620–625
Yagcia MB, Bolcab S, Heutsc JPA, Minga W, de Witha G (2011) Antimicrobial polyurethane coatings based on ionic liquid quaternary ammonium compounds. Prog Org Coat 72:343–347
Yi F, Peng Y, Song G (2005) Microwave-assisted liquid-phase synthesis of methyl 6-amino-5-cyano-4-aryl-2-methyl-4H-pyran-3-carboxylate using functional ionic liquid as soluble support. Tetrahedron Lett 46:3931–3933
Zarrouk A, Messali M, Aouad MR, Zarrok H, Salghi R, Hammouti B, Chetouani A, Al-Deyab SS (2012a) Some new ionic liquids derivatives: synthesis, characterization and comparative study towards corrosion of C-steel in acidic media. J Chem Pharm Res 4:3427–3436
Zarrouk A, Messali M, Zarrok H, Salghi R, Ali AA-S, Hammouti B, Al-Deyab SS, Bentiss F (2012b) Synthesis, characterization and comparative study of new functionalized imidazolium-based ionic liquids derivatives towards corrosion of C38 steel in molar hydrochloric acid. Int J Electrochem Sci 7:6998–7015
Zhao S, Zhao E, Shen P, Zhao M, Sun J (2008) An atom-efficient and practical synthesis of new pyridinium ionic liquids and application in Morita–Baylis–Hillman reaction. Ultrason Sonochem 15:955–959
Acknowledgments
We gratefully acknowledge the financial support from Taibah University (Grant 636). Prof. T. Ben Hadda would like to thank the ACTELION; the Biopharmaceutical Company of Swiss, for the online molecular properties calculations.
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Messali, M., Aouad, M.R., Ali, A.AS. et al. Synthesis, characterization, and POM analysis of novel bioactive imidazolium-based ionic liquids. Med Chem Res 24, 1387–1395 (2015). https://doi.org/10.1007/s00044-014-1211-x
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DOI: https://doi.org/10.1007/s00044-014-1211-x