Have a personal or library account? Click to login
Synthesis of bioactive quinazolin-4(3H)-one derivatives via microwave activation tailored by phase-transfer catalysis Cover

Synthesis of bioactive quinazolin-4(3H)-one derivatives via microwave activation tailored by phase-transfer catalysis

Open Access
|Jan 2020

References

  1. 1. J. He, X. Wang, X. Zhao, Y. J. Liang, H. He and L. Fu, Synthesis and antitumor activity of novel quinazoline derivatives containing thiosemicarbazide moiety, Eur. J. Med. Chem.54 (2012) 925–930; https://doi.org/10.1016/j.ejmech.2012.06.00310.1016/j.ejmech.2012.06.003
  2. 2. C. D. Haffner, J. D. Becherer, E. E. Boros, R. Cadilla, T. Carpenter, D. Cowan, D. N. Deaton, Y. Guo, W. Harrington, B. R. Henke, M. R. Jeune, I. Kaldor, N. Milliken and K. G. Petrov, Discovery, synthesis, and biological evaluation of thiazoloquin(az)olin(on)es as potent CD38 inhibitors, J. Med. Chem.58 (2015) 3548–3571; https://doi.org/10.1021/jm502009h10.1021/jm502009h
  3. 3. R. V. Sheorey, A. Thangathiruppathy and V. Alagarsamy, Synthesis and pharmacological evaluation of 3-propyl-2-substitutedamino-3h-quinazolin-4-ones as analgesic and anti-inflammatory agents, J. Heterocycl. Chem.53 (2016) 1371–1377; https://doi.org/10.1002/jhet.197310.1002/jhet.1973
  4. 4. M. Hrast, K. Rožman, M. Jukič, D. Patin, S. Gobec and M. Sova, Synthesis and structure-activity relationship study of novel quinazolinone-based inhibitors of MurA, Bioorg. Med. Chem.27 (2017) 3529–3533; https://doi.org/10.1016/j.bmcl.2017.05.06410.1016/j.bmcl.2017.05.064
  5. 5. M. Sarfraz, N. Sultana, U. Rashid, M. S. Akram, A. Sadiq and M. I. Tariq, Synthesis, biological evaluation and docking studies of 2,3-dihydroquinazolin-4(1H)-one derivatives as inhibitors of cholinesterases, Bioorg. Chem.70 (2017) 237–244; https://doi.org/10.1016/j.bioorg.2017.01.00410.1016/j.bioorg.2017.01.004
  6. 6. I. K. Kacker and S. H. Zaheer, Reactions of substituted 3:4-dihydro-4-oxoquinazolines with Grignard reagents, J. Chem. Soc. (1956) 415–418; https://doi.org/10.1039/JR956000041510.1039/jr9560000415
  7. 7. J. F. Wolfe, T. L. Rathman, M. C. Sleevi, J. A. Campbell and T. D. Greenwood, Synthesis and anticonvulsant activity of some new 2-substituted 3-aryl-4(3H)-quinazolinones, J. Med. Chem.33 (1990) 161–166; https://doi.org/10.1021/jm00163a02710.1021/jm00163a027
  8. 8. J. Bergman and A. Brynolf, Synthesis of chrysogine, a metabolite of Penicillium chrysogenum and some related 2-substituted 4-(3H)-quinazolinones, Tetrahedron46 (1990) 1295–1310; https://doi.org/10.1016/s0040-4020(01)86694-110.1016/S0040-4020(01)86694-1
  9. 9. S. Eguchi, T. Suzuki, T. Okawa, Y. Matsushita, E. Yashima and Y. Okamoto, Synthesis of optically active vasicinone based on intramolecular aza-Wittig reaction and asymmetric oxidation, J. Org. Chem.61 (1996) 7316–7319; https://doi.org/10.1021/jo960928310.1021/jo960928311667656
  10. 10. K. Smith, G. A. El-Hiti and M. F. Abdel-Megeed, Regioselective lithiation of chiral 3-acylamino-2-alkylquinazolin-4(3H)-ones: Application in synthesis, Synthesis (issue 13) (2004) 2121–2130; https://doi.org/10.1055/s-2004-82916910.1055/s-2004-829169
  11. 11. C. D. Dago, C. N. Ambeu, W.-K. Coulibaly, Y.-A. Beekro, J. Mamyrbeekova, A. Defontaine, B. Baratte, S. Bach, S. Ruchaud, R. Le Gueevel, M. Ravache, A. Corlu and J.-P. Bazureau, Synthetic development of new 3-(4-arylmethylamino)butyl-5-arylidene-rhodanines under microwave irradiation and their effects on tumor cell lines and against protein kinases, Molecules20 (2015) 12412–12435; https://doi.org/10.3390/molecules20071241210.3390/molecules200712412633231826184130
  12. 12. M. A. El-Hashash, T. M. Abdel-Rahman and Y. A. El-Badry, Synthesis and behavior of 2-carboxyvinyl-6,8-dibromo-4H-3,1-benzoxazin-4-one towards nitrogen, carbon and sulphur nucleophiles, Indian J. Chem.45B (2006) 1470–1477; https://doi.org/10.1002/chin.20064103010.1002/chin.200641030
  13. 13. H. Chai, J. Li, L. Yang, H. Lu, Z. Qi and D. Shi, Copper-catalyzed tandem N-arylation/condensation: synthesis of quinazolin-4(3H)-ones from 2-halobenzonitriles and amides, RSC Adv.4 (2014) 44811–44814; https://doi.org/10.1039/c4ra08031a10.1039/C4RA08031A
  14. 14. G. A. Obafemi, O. A. Fadare, J. P. Jasinski, S. P. Millikan, E. M. Obuotor, E. O. Iwalewa, S. O. Famuyiwa, K. Sanusi, Y. Yilmaz and U. Ceylan, Microwave-assisted synthesis, structural characterization, DFT studies, antibacterial and antioxidant activity of 2-methyl-4-oxo-1,2,3,4-tetrahydroquinazoline-2-carboxylic acid, J. Mol. Str.1155 (2018) 610–622; https://doi.org/10.1016/j.molstruc.2017.11.01810.1016/j.molstruc.2017.11.018
  15. 15. M. A. El-Hashash and Y. A. El-Badry, Synthesis of a novel series of 2,3-disubstituted quinazolin-4(3H)-ones as a product of a nucleophilic attack at C(2) of the corresponding 4H-3,1-benzoxazin-4-one, Helv. Chim. Acta94 (2011) 389–396; https://doi.org/10.1002/hlca.20100023010.1002/hlca.201000230
  16. 16. D. H. Hieu, D. T. Anh, N. M. Tuan, P-T. Hai, L.-T.-T. Huong, J. Kim, J. S. Kang, T. K. Vu, P. T. P. Dung, S.-B. Han, N.-H. Nam and N.-D. Hoa, Design, synthesis and evaluation of novel N-hydroxybenzamides/N-hydroxypropenamides incorporating quinazolin-4(3H)-ones as histone deacetylase in hibitors and antitumor agents, Bioorg. Chem.76 (2018) 258–267; https://doi.org/10.1016/j.bioorg.2017.12.00710.1016/j.bioorg.2017.12.00729223029
  17. 17. Y. A. El-Badry, N. A. Anter and H. S. El-Sheshtawy, Synthesis and evaluation of new polysubstituted quinazoline derivatives as potential antimicrobial agents, Pharma Chem.4 (2012) 1361–1370.
  18. 18. C. Valgas, S. De Souza, E. Smaenia and A. Smaenia, Screening methods to determine antibacterial activity of natural products, Braz. J. Microbiol.38 (2007) 369–380; https://doi.org/10.1590/s1517-8382200700020003410.1590/S1517-83822007000200034
  19. 19. A. Monks, D. Scudiero, P. Skehan, R. Shoemaker, K. Paull, D. Vistica, C. Hose, J. Langley, P. Cronise, A. Vaigro-Wolff, M. Gray-Goodrich, H. Campbell, J. Mayo and M. Boyd, Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines, J. Natl. Cancer Inst.83 (1991) 757–766; https://doi.org/10.1093/jnci/83.11.75710.1093/jnci/83.11.7572041050
  20. 20. M. R. Boyd and K. D. Paull, Some practical considerations and applications of the national cancer institute in vitro anticancer drug discovery screen, Drug Develop. Res.34 (1995) 91–109; https://doi.org/10.1002/ddr.43034020310.1002/ddr.430340203
  21. 21. R. H. Shoemaker, The NCI60 human tumour cell line anticancer drug screen, Nat. Rev. Cancer6 (2006) 813–823; https://doi.org/10.1038/nrc195110.1038/nrc195116990858
  22. 22. S. Fozooni and S. Firoozi, Microwave-assisted synthesis of new quinazolinone and (dihydroquinazolinylphenyl)oxazolone derivatives, Chem. Heterocycl. Compd.51 (2015) 340–345; https://doi.org/10.1007/s10593-015-1705-610.1007/s10593-015-1705-6
  23. 23. I. Nouira, I. K. Kostakis, C. Dubouilh and E. Chosson, Decomposition of formamide assisted by microwaves, a tool for synthesis of nitrogen-containing heterocycles, Tetrahedron Lett.49 (2008) 7033–7036; https://doi.org/10.1016/j.tetlet.2008.09.13510.1016/j.tetlet.2008.09.135
  24. 24. A. Loupy, A. Petit and D. Bogdal, Microwaves and Phase-Transfer Catalysis, in Microwaves in Organic Synthesis (Ed. A. Loupy), 2nd ed., Wiley-VCH Verlag GmbH & KgaA, Weinheim 2006, pp. 278–280.10.1002/9783527619559.ch6
  25. 25. A. Loupy, A. Petit, J. Hamelin, F. Texier-Boullet, P. Jacquault and D. Mathé, New solvent-free organic synthesis using focused microwaves, Synthesis (1998) 1213–1234; https://doi.org/10.1055/s-1998-608310.1055/s-1998-6083
  26. 26. Z.-Z. Huang and L.-S. Zu, Rapid N-alkylation of benzoxazinones and benzothiazinones under microwave irradiation, Org. Prep. Proc. Int.28 (1996) 121–123; https://doi.org/10.1080/0030494960935591710.1080/00304949609355917
  27. 27. M. Gupta and B. P. Wakhloo, Tetrabutylammonium bromide mediated Knoevenagel condensation in water: Synthesis of cinnamic acids, ARKIVOC15 (2007) 94–98; https://doi.org/10.3998/ark.5550190.0008.11010.3998/ark.5550190.0008.110
  28. 28. V. Blokzijl and J. B. F. N. Engberts, Hydrophobic effects. Opinions and facts, Angew. Chem. Int. Edit.32 (1993) 1545–1579.10.1002/anie.199315451
  29. 29. F. Bigi, M. L. Conforti, R. Maggi, A. Piccinno and G. Sartori, Clean synthesis in water: uncatalyzed preparation of ylidenemalononitriles, Green Chem.2 (2000) 101–103; https://doi.org/10.1039/b001246g10.1039/b001246g
  30. 30. M. C. Alley, D. Scudiero, P. A. Monks, M. L. Hursey and M. J. Czerwinski, Feasibility of drug screening with panels of human tumor cell lines using a micro-culture tetrazolium assay, Cancer Res.48 (1988) 589–601.
DOI: https://doi.org/10.2478/acph-2020-0001 | Journal eISSN: 1846-9558 | Journal ISSN: 1330-0075
Language: English
Page range: 161 - 178
Accepted on: Apr 6, 2019
|
Published on: Jan 16, 2020
In partnership with: Paradigm Publishing Services
Publication frequency: 4 issues per year
Related subjects:

© 2020 Yaser A. El-Badry, Mahr A. El-Hashash, Khalil Al-Ali, published by Croatian Pharmaceutical Society
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.