Login Register Cart 0
Generic placeholder image

Current Organic Synthesis

Editor-in-Chief

ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

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

Synthesis and Cytotoxic Activity of Quinazoline-benzofuran Conjugates

Author(s): Yixin Liu, Nanting Zou, Minxin Li, Chunping Wan* and Zewei Mao*

Volume 21, Issue 7, 2024

Published on: 01 August, 2023

Page: [928 - 940] Pages: 13

DOI: 10.2174/1570179420666230623113535

Price: $65

Abstract

Aims: In order to study on structure-activity relationships of benzofurans.

Background: Benzofuran is a kind of natural compound widely existing in nature with pharmacological effects. The development of new anticancer benzofuran derivatives has attracted more and more attention.

Methods: We have introduced an active quinazoline unit into piperazine-substituted benzofuran, prepared a series of quinazoline-benzofuran compounds, and evaluated cytotoxic activity against a panel of human tumor cell lines by MTT assay.

Results: 48 novel quinazoline-substituted benzofuran derivatives have been prepared, and in vitro, cytotoxic activity against five human tumor cell lines was evaluated. The results indicated that some quinazoline-benzofuran conjugates showed selective inhibitory activity against tumor cell lines.

Conclusion: We have found that compound 14x displayed excellent cytotoxic activity, which could be considered a potential anticancer agent.

Keywords: Quinazoline, benzofuran, conjugates, synthesis, cytotoxic activity, anticancer.

« Previous Next »
Graphical Abstract

[1]
Siegel, R.L.; Miller, K.D.; Wagle, N.S.; Jemal, A.; Smith, R.A.; Jemal, A. Cancer statistics, 2023. CA Cancer J. Clin., 2023, 73(1), 17-48.
[http://dx.doi.org/10.3322/caac.21763] [PMID: 36633525]
[2]
Das, B.; Baidya, A.T.K.; Mathew, A.T.; Yadav, A.K.; Kumar, R. Structural modification aimed for improving solubility of lead compounds in early phase drug discovery. Bioorg. Med. Chem., 2022, 56, 116614.
[http://dx.doi.org/10.1016/j.bmc.2022.116614] [PMID: 35033884]
[3]
Radadiya, A.; Shah, A. Bioactive benzofuran derivatives: An insight on lead developments, radioligands and advances of the last decade. Eur. J. Med. Chem., 2015, 97, 356-376.
[http://dx.doi.org/10.1016/j.ejmech.2015.01.021] [PMID: 25703339]
[4]
Khanam, H. Shamsuzzaman, Bioactive Benzofuran derivatives: A review. Eur. J. Med. Chem., 2015, 97, 483-504.
[http://dx.doi.org/10.1016/j.ejmech.2014.11.039] [PMID: 25482554]
[5]
Chand, K. Rajeshwari; Hiremathad, A.; Singh, M.; Santos, M.A.; Keri, R.S. A review on antioxidant potential of bioactive heterocycle benzofuran: Natural and synthetic derivatives. Pharmacol. Rep., 2017, 69(2), 281-295.
[http://dx.doi.org/10.1016/j.pharep.2016.11.007] [PMID: 28171830]
[6]
Nair, S.R.; Baire, B. Recent Dearomatization Strategies of Benzofurans and Benzothiophenes. Asian J. Org. Chem., 2021, 10(5), 932-948.
[http://dx.doi.org/10.1002/ajoc.202100025]
[7]
Matsuo, Y.; Yamaguchi, E.; Hakamata, R.; Ootomo, K.; Takatori, K.; Fukaya, H.; Mimaki, Y. Benzofuran and coumarin derivatives from the root of Angelica dahurica and their PPAR-γ ligand-binding activity. Phytochemistry, 2020, 173, 112301.
[http://dx.doi.org/10.1016/j.phytochem.2020.112301] [PMID: 32092557]
[8]
Nevagi, R.J.; Dighe, S.N.; Dighe, S.N. Biological and medicinal significance of benzofuran. Eur. J. Med. Chem., 2015, 97, 561-581.
[http://dx.doi.org/10.1016/j.ejmech.2014.10.085] [PMID: 26015069]
[9]
Adem, F.A.; Kuete, V.; Mbaveng, A.T.; Heydenreich, M.; Ndakala, A.; Irungu, B.; Efferth, T.; Yenesew, A. Cytotoxic benzylbenzofuran derivatives from Dorstenia kameruniana. Fitoterapia, 2018, 128, 26-30.
[http://dx.doi.org/10.1016/j.fitote.2018.04.019] [PMID: 29715541]
[10]
Naik, R.; Harmalkar, D.S.; Xu, X.; Jang, K.; Lee, K. Bioactive benzofuran derivatives: Moracins A–Z in medicinal chemistry. Eur. J. Med. Chem., 2015, 90, 379-393.
[http://dx.doi.org/10.1016/j.ejmech.2014.11.047] [PMID: 25461329]
[11]
Xu, Z.; Xu, D.; Zhou, W.; Zhang, X. Therapeutic potential of naturally occurring benzofuran derivatives and hybrids of benzofurans with other pharmacophores as antibacterial agents. Curr. Top. Med. Chem., 2022, 22(1), 64-82.
[http://dx.doi.org/10.2174/1568026621666211122162439] [PMID: 34809548]
[12]
Korthikunta, V.; Singh, R.; Srivastava, R.; Pandey, J.; Srivastava, A.; Chaturvedi, U.; Mishra, A.; Srivastava, A.K.; Tamrakar, A.K.; Tadigoppula, N. Design, synthesis, and evaluation of benzofuran-based chromenochalcones for antihyperglycemic and antidyslipidemic activities. RSC Medicinal Chemistry, 2023, 14(3), 470-481.
[http://dx.doi.org/10.1039/D2MD00341D] [PMID: 36970150]
[13]
Mao, Z.W.; Zheng, X.; Lin, Y.P.; Hu, C.Y.; Wang, X.L.; Wan, C.P.; Rao, G.X. Design, synthesis and anticancer activity of novel hybrid compounds between benzofuran and N-aryl piperazine. Bioorg. Med. Chem. Lett., 2016, 26(15), 3421-3424.
[http://dx.doi.org/10.1016/j.bmcl.2016.06.055] [PMID: 27371110]
[14]
Ma, Y.; Zheng, X.; Gao, H.; Wan, C.; Rao, G.; Mao, Z. Design, Synthesis, and Biological Evaluation of Novel Benzofuran Derivatives Bearing N-Aryl Piperazine Moiety. Molecules, 2016, 21(12), 1684.
[http://dx.doi.org/10.3390/molecules21121684] [PMID: 27941680]
[15]
Gao, H.; Zhang, X.; Pu, X.J.; Zheng, X.; Liu, B.; Rao, G.X.; Wan, C.P.; Mao, Z.W. 2-Benzoylbenzofuran derivatives possessing piperazine linker as anticancer agents. Bioorg. Med. Chem. Lett., 2019, 29(6), 806-810.
[http://dx.doi.org/10.1016/j.bmcl.2019.01.025] [PMID: 30709651]

Rights & Permissions Print Cite
Article Metrics
34
3
Wayfinder Image
© 2024 Bentham Science Publishers | Privacy Policy