Login Register Cart 0
Generic placeholder image

Current Microwave Chemistry

Editor-in-Chief

ISSN (Print): 2213-3356
ISSN (Online): 2213-3364

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

A Novel Powerful Choline Chloride - Thiourea/Sulfuric Acid: An Efficient and Recyclable Catalyst Used for the Microwave-assisted Synthesis of Quinazolin- 4(3H)-one Derivatives Used as Antibacterial Agents in Green Media

Author(s): Fateme Haji Norouzi, Naser Foroughifar*, Alireza Khajeh-Amiri and Hoda Pasdar

Volume 9, Issue 1, 2022

Published on: 14 June, 2022

Page: [18 - 29] Pages: 12

DOI: 10.2174/2213335609666220324145341

Price: $65

Abstract

Background: Choline chloride-thiourea/sulfuric acid is a powerful and efficient green catalyst used for one-pot synthesis of quinazoline-4 (3H)-one derivatives via a reaction between various amines, acetic anhydride, and anthranilic acid under microwave irradiation and solventfree conditions (4a-q). Microwave irradiation, which is a faster, more cost-effective, less energyintensive, and more efficient method than conventional heating, has been used to synthesize some quinazolinone derivatives.

Introduction: For the past ten years, one of the major subjects in synthetic organic chemistry has been green synthesis, which has used efficient and environmentally friendly methods to synthesize biological compounds. The use of catalysts has significant advantages, including ease of preparation and separation, chemical and thermal stability, and environmental friendliness due to features such as reusability, low cost, and efficient and easy workup techniques. Therefore, the mechanism is performed by a non-toxic organic catalyst that uses the least amount of energy and chemical reactants in accordance with the principles of green chemistry and the least waste.

Methods: One-pot and sequential addition methods have been used to synthesize quinazolinone derivatives. In the sequential addition method, the reaction was started by adding acetic anhydride and anthranilic acid to the reaction vessel under microwave irradiation and continued by adding choline chloride thiourea/sulfuric acid as efficient, recyclable green catalysts and the desired amine. In vitro, the well diffusion method against different pathogenic strains was used to evaluate the antimicrobial activity of quinazoline-4 (3H)-one derivatives. Pathogenic strains used were Candida albicans ATCC 10231 (yeast), Aspergillus niger ATCC 16404 (fungus), Escherichia coli ATCC 8739, Pseudomonas aeruginosa ATCC 9027 (bacteria) and ATCC 6538, and Staphylococcus aureus S. epidermidis ATCC 12228. Pyrimidine-containing compounds, in which the 3- hydroxyl, 2,5-dimethoxy, 4-bromo, 4‐methoxy, and 4‐chloro groups are attached to the phenyl ring of pyrimidine, exhibit antimicrobial properties.

Results: In a short reaction time, a variety of biologically active quinazolinone derivatives were synthesized with high efficiency. According to the results, it was found that with aliphatic amines, the reaction time was shorter, and the reaction efficiency was higher. Products synthesized from aromatic amines had more antibacterial properties.

Conclusion: In this work, a variety of 2-methyl-quinazoline-4 (3H)-one derivatives (4a–q) were synthesized as potent antibacterial agents under microwave irradiation and solvent-free conditions in the presence of ChCl-thiourea/H2SO4 as an efficient, eco-friendly, and recyclable catalyst.

Keywords: Anthranilic acid, choline chloride-thiourea/sulfuric acid, green synthesis, microwave irradiation, quinazolinone, antibacterial agent, recyclability.

« Previous Next »
Graphical Abstract

[1]
Gedye, R.N. The rapid synthesis of organic compounds in microwave ovens. Can. J. Chem., 2011, 66(1), 17-26.
[http://dx.doi.org/10.1139/v88-003]
[2]
Hayes, B.L. Microwave Synthesis-Chemistry at the Speed of Light; CEM Publishing, 2002.
[3]
Abtahi, B.; Tavakol, H. Choline chloride-urea deep eutectic solvent as an efficient media for the synthesis of propargylamines via organocuprate intermediate. Appl. Organomet. Chem., 2020, 34(11), 5895-5906.
[http://dx.doi.org/10.1002/aoc.5895]
[4]
Dabiri, M.; Baghbanzadeh, M.; Delbari, A.S. Novel and efficient one-pot tandem synthesis of 2-styryl-substituted 4(3H)-quinazolinones. J. Comb. Chem., 2008, 10(5), 700-703.
[http://dx.doi.org/10.1021/cc800067g] [PMID: 18671434]
[5]
Preethi, T.; Padmapriya, M.P.; Abarna, B.; Rajarajeswari, G.R. Choline chloride–zinc chloride ionic liquid as a green template for the sol–gel synthesis of mesoporous titania. RSC Advances, 2017, 7(17), 10081-10091.
[http://dx.doi.org/10.1039/C6RA28478G]
[6]
Molnar, M.; Klenkar, J.; Tarnai, T. Eco-friendly rapid synthesis of 3-substituted-2-thioxo-2, 3-dihydroquinazolin-4 (1H)-ones in choline chloride-based deep eutectic solvent. Synth. Commun., 2017, 47(11), 1040-1045.
[http://dx.doi.org/10.1080/00397911.2017.1291815]
[7]
Handy, S.T. Greener solvents: Room temperature ionic liquids from biorenewable sources. Chemistry, 2003, 9(13), 2938-2944.
[http://dx.doi.org/10.1002/chem.200304799]
[8]
Khajavi, M. S.; Sadat Hosseini, S. S.; Montazari, N. Microwave irradiation promoted reactions of benzoxazin-4-ones with primary amines.preparation of 4 (3H)-quinazolinones. Iran. J. Chem., 18, (1), 30-32.
[9]
El-Badry, Y.A.; El-Hashash, M.A.; Al-Ali, K. Synthesis of bioactive quinazolin-4(3H)-one derivatives via microwave activation tailored by phase-transfer catalysis. Acta Pharm., 2020, 70(2), 161-178.
[http://dx.doi.org/10.2478/acph-2020-0001] [PMID: 31955144]
[10]
Khan, I.; Ibrar, A.; Abbas, N.; Saeed, A. Recent advances in the structural library of functionalized quinazoline and quinazolinone scaffolds: Synthetic approaches and multifarious applications. Eur. J. Med. Chem., 2014, 76, 193-244.
[http://dx.doi.org/10.1016/j.ejmech.2014.02.005] [PMID: 24583357]
[11]
D’yakonov, A.L.; Telezhenetskaya, M.V. Quinazoline alkaloids in nature. Chem. Nat. Compd., 1997, 33(3), 221-267.
[http://dx.doi.org/10.1007/BF02234869]
[12]
He, L.; Li, H.; Chen, J.; Wu, X-F. Recent advances in 4(3H)-. RSC Advances, 2014, 4(24), 12065-12077.
[http://dx.doi.org/10.1039/C4RA00351A]
[13]
Alafeefy, A.M.; Kadi, A.A.; Al-Deeb, O.A.; El-Tahir, K.E.; Al-Jaber, N.A. Synthesis, analgesic and anti-inflammatory evaluation of some novel quinazoline derivatives. Eur. J. Med. Chem., 2010, 45(11), 4947-4952.
[http://dx.doi.org/10.1016/j.ejmech.2010.07.067] [PMID: 20817329]
[14]
Hassanzadeh, F.; Sadeghi-Aliabadi, H.; Nikooei, S.; Jafari, E.; Vaseghi, G. Synthesis and cytotoxic evaluation of some derivatives of triazole-quinazolinone hybrids. Res. Pharm. Sci., 2019, 14(2), 130-137.
[http://dx.doi.org/10.4103/1735-5362.253360] [PMID: 31620189]
[15]
Jafari, E.; Khajouei, M.R.; Hassanzadeh, F.; Hakimelahi, G.H.; Khodarahmi, G.A. Quinazolinone and quinazoline derivatives: Recent structures with potent antimicrobial and cytotoxic activities. Res. Pharm. Sci., 2016, 11(1), 1-14.
[PMID: 27051427]
[16]
Ram, V.J. Farhanullah., Tripathi, B.K.; Srivastava, A.K. Synthesis and antihyperglycemic activity of suitably functionalized 3H-quinazolin-4-ones. Bioorg. Med. Chem., 2003, 11(11), 2439-2444.
[http://dx.doi.org/10.1016/S0968-0896(03)00142-1] [PMID: 12735990]
[17]
Abuelizz, H.A.; Dib, R.E.; Marzouk, M.; Anouar, E-H.; Maklad, A.Y.; N. Attia, H. Al-Salahi, R. Molecular docking and anticonvulsant activity of newly synthesized quinazoline derivatives. Molecules, 2017, 22(7), 1094-1107.
[http://dx.doi.org/10.3390/molecules22071094] [PMID: 28665338]
[18]
Sen, D.; Banerjee, A.; Ghosh, A.K.; Chatterjee, T.K. Synthesis and antimalarial evaluation of some 4-quinazolinone derivatives based on febrifugine. J. Adv. Pharm. Technol. Res., 2010, 1(4), 401-405.
[http://dx.doi.org/10.4103/0110-5558.76439] [PMID: 22247880]
[19]
Kamyar, K.; Safakish, M.; Zebardast, T.; Hajimahdi, Z.; Zarghi, A. Molecular docking and QSAR study of 2-benzoxazolinone, quinazoline and diazocoumarin derivatives as anti-HIV-1 agents. Iran. J. Pharm. Res., 2019, 18(3), 1253-1263.
[PMID: 32641936]
[20]
Purkhosrow, A.; Khalili, A.; Chih Ho, A.; Mowlazadeh Haghighi, S.; Fakher, S.; Khalafi-Nezhad, A. Highly efficient, one pot, solvent and catalyst, free synthesis of novel quinazoline derivatives under ultrasonic irradiation and their vasorelaxant activity isolated thoracic aorta of rat. Iran. J. Pharm. Res., 2019, 18(2), 607-619.
[PMID: 31531045]
[21]
Haggam, R.A.; Soylem, E.A.; Assy, M.G.; Arastiedy, M.F. Synthesis and antimicrobial evaluation of new series of quinazolin-5-one derivatives. J. Iran. Chem., 2020, 17, 1715-1723.
[22]
Demeunynck, M.; Baussanne, I. Survey of recent literature related to the biologically active 4(3H)-quinazolinones containing fused heterocycles. Curr. Med. Chem., 2013, 20(6), 794-814.
[PMID: 23276134]
[23]
Maheswari, C.U.; Kumar, G.S.; Venkateshwar, M.; Kumar, R.A.; Kantam, M.L.; Reddy, K.R. Highly efficient one‐pot synthesis of 2‐substituted quinazoline and 4H‐benzo [d][1, 3] oxazines via cross-dehydrogenative coupling using sodium hypochlorite. Adv. Synth. Catal., 2010, 352(2‐3), 341-346.
[http://dx.doi.org/10.1002/adsc.200900715]
[24]
Dervis, G. One-pot three-component synthesis of novel 2-(3-nitro-phenyl)-quinazoline-4-carboxylic acid derivatives. J. Heterocycl. Chem., 2019, 12(56), 3343-3353.
[http://dx.doi.org/10.1002/jhet.3731]
[25]
Guoli, H. Bo.; Mingyu, T.; Chen, Y. Ammonium chloride–catalyzed one-pot synthesis of 4(3H)-quinazolinones under solvent-free conditions. Synth. Commun., 2014, 12(44), 1786-1794.
[http://dx.doi.org/10.1080/00397911.2013.873467]
[26]
Sheng-Li, C.; Mei, Z.; Yu-Ping, F.; Yu-Yang, J.; Nan, Z. Synthesis of 3-Aryl-4(3H)-quinazolinones from anthranilic acids and triethyl orthoformate. Synth. Commun., 2008, 13(38), 2227-2236.
[http://dx.doi.org/10.1080/00397910802026584]
[27]
Komar, M.; Molnar, M.; Jukić, M.; Glavaš-Obrovac, L.; Opačak-Bernardi, T. Green chemistry approach to the synthesis of 3-substituted-quinazolin-4 (3H)-ones and 2-methyl-3-substituted-quinazolin-4 (3 h)-ones and biological evaluation. Green Chem. Lett. Rev., 2020, 13(2), 93-101.
[http://dx.doi.org/10.1080/17518253.2020.1741694]
[28]
Akhavan, M.; Foroughifar, N.; Pasdar, H.; Bekhradnia, A. Green synthesis, biological activity evaluation, and molecular docking studies of aryl alkylidene 2, 4-thiazolidinedione and rhodanine derivatives as antimicrobial agents. Comb. Chem. High Throughput Screen., 2019, 22(10), 716-727.
[http://dx.doi.org/10.2174/1386207322666191127103122] [PMID: 31775594]
[29]
Akhavan, M.; Bekhradnia, A. Stereoselective synthesis of spirocyclic pyrrolidines/pyrrolizidines/pyrrolothiazolidines using l-proline functionalized manganese ferrite nanorods as a novel heterogeneous catalyst. RSC Advances, 2021, 11(24), 14755-14768.
[http://dx.doi.org/10.1039/D1RA00841B]
[30]
Esam, Z.; Akhavan, M.; Bekhradnia, A. One‐pot multicomponent synthesis of novel 2‐(piperazin‐1‐yl) quinoxaline and benzimidazole derivatives, using a novel sulfamic acid functionalized Fe3O4 MNPs as highly effective nanocatalyst. Appl. Organomet. Chem., 2021, 35(1), e6005.
[31]
Akhavan, M.; Foroughifar, N.; Pasdar, H.; Bekhradnia, A. Green chemical synthesis and biological evaluation of novel N-substituted rhodanine derivatives as potential antifungal agents. J. Mazandaran Univ. Med. Sci., 2020, 29(182), 82-90.
[32]
Kudale, V.S.; Wang, J.J. Metal-free C–H methylation and acetylation of heteroarenes with PEG-400. Green Chem., 2020, 22(11), 3506-3511.
[http://dx.doi.org/10.1039/D0GC01183E]
[33]
Nakano, H.; Kutsumura, N.; Saito, T. Functionalized carbodiimide mediated synthesis of 2, 3-disubstituted quinazolin-4 (3H)-ones via the tandem strategy of C-nucleophilic addition and intramolecular NH-substitution cyclization. Synthesis, 2012, 44(20), 3179-3184.
[http://dx.doi.org/10.1055/s-0032-1316773]
[34]
Malhotra, S.; Koul, S.K.; Singh, S.; Singh, G.B.; Dhar, K.L. Studies on some biologically active azepinoquinazolines.part 2. An approach to effective antiinflammatory drugs. ChemInform, 1989, 20(30)
[35]
Ajani, O.O. Expeditious synthesis and spectroscopic characterization of 2-methyl-3-substituted-quinazolin-4 (3H)-one derivatives. Orient. J. Chem., 2017, 33(2), 562-574.
[http://dx.doi.org/10.13005/ojc/330203]
[36]
Khodarahmi, G.; Jafari, E.; Hakimelahi, G.; Abedi, D. Synthesis of some new quinazolinone derivatives and evaluation of their antimicrobial activities. IJPR, 2012, 11(3), 789-797.
[37]
Salehi, P.; Dabiri, M.; Zolfigol, M.A.; Baghbanzadeh, M. A new approach to the facile synthesis of mono- and disubstituted quinazolin-4(3H)-ones under solvent-free conditions. Tetrahedron Lett., 2005, 46(41), 7051-7053.
[http://dx.doi.org/10.1016/j.tetlet.2005.08.043]
[38]
Shu-Liang, W.; Ke, Y.; Chang-Sheng, Y.; Xiang-Shan, W. Green synthesis of quinazolinone derivatives catalyzed by iodine in ionic liquid. Synth. Commun., 2012, 42(3), 524340.
[http://dx.doi.org/10.1080/00397911.2010.524340.341-349]
[39]
Barot, K.P.; Manna, K.S.; Ghate, M.D. Design, synthesis and antimicrobial activities of some novel 1,3,4-thiadiazole, 1,2,4-triazole-5-thione and 1,3-thiazolan-4-one derivatives of benzimidazole. J. Saudi Chem. Soc., 2017, 21(1), S35-S43.
[http://dx.doi.org/10.1016/j.jscs.2013.09.010]
[40]
Norrington, F.E.; Hyde, R.M.; Williams, S.G.; Wootton, R. Physiochemical-activity relations in practice. 1. A rational and self-consistent data bank. J. Med. Chem., 1975, 18(6), 604.
[http://dx.doi.org/10.1021/jm00240a016] [PMID: 1151976]

Rights & Permissions Print Cite
Article Metrics
44
1
© 2024 Bentham Science Publishers | Privacy Policy