Novel quinazolin‐4(3<i>H</i>)‐one linked to 1,2,3‐triazoles: Synthesis and anticancer activity

Safavi, Maliheh; Ashtari, Arsalan; Khalili, Faezeh; Mirfazli, Seyedeh Sara; Saeedi, Mina; Ardestani, Sussan K.; Ranjbar, Parviz Rashidi; Tehrani, Maliheh Barazandeh; Larijani, Bagher; Mahdavi, Mohammad

doi:10.1111/cbdd.13203

Cited by 42 publications

(19 citation statements)

References 23 publications

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“…The known systems fused to triazoles are pyridines, pyridazines, quinazolines, pyrazines and triazines(15). Hybrid structures of quinazolinone-triazole have been reported with anticancer (28), antibacterial (151629), anti-malaria (30) and anticonvulsant (31) activities.…”

Section: Discussionmentioning

confidence: 99%

Synthesis and cytotoxic evaluation of some derivatives of triazole-quinazolinone hybrids

et al. 2019

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Triazoles and quinazolinones are important heterocyclic structures with diverse biological properties including cytotoxic, antibacterial, antifungal and anticonvulsant activities. Due to valuable cytotoxic effects of both triazole and quinazoline derivatives, in this study a series of quinazolinone-triazole hybrids were synthesized in a multiple-step reaction procedure. 3-Amino-quinazolinone derivatives were treated with chloroacetyl chloride in the presence of dichloromethane/triethylamine to afford 2-chloro -N-(4-oxo-2- quinazolin3 (3H)-yl) acetamide derivatives. The reaction of resultants with 4-mehyl-4-H-1, 2, 4-triazole-3- thiol in dry acetone and potassium carbonate led to the formation of final products. Synthesized compounds were evaluated for their cytotoxic effects against MCF-7 and Hela cell lines using MTT colorimetric assay. Amongst tested compounds, 6a showed the highest cytotoxic activity against MCF7 cell line at all tested concentrations while compounds 6b and 6c indicated mild cytotoxic effects against Hela cell line at highest tested concentration reducing cell viability about 40%. The IC50 values of tested compounds revealed that the MCF-7 is more susceptible to the compound 6a.

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Section: Discussionmentioning

confidence: 99%

Synthesis and cytotoxic evaluation of some derivatives of triazole-quinazolinone hybrids

et al. 2019

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“…Most cytotoxic agents cause cell cycle arrest, either as the direct consequence of regulating cell cycle regulators, or as the secondary effect of modifying other cell components 22 . In order to study the effect of compound 5k on cell cycle, A549 cells were treated by compound 5k or Gefitinib for 48 h, then the cells were strained by PI and examined using flow cytometry.…”

Section: Effects Of Compound 5k On Cell Cycle Of A549 Cell Linementioning

confidence: 99%

Design, synthesis and in vitro biological evaluation of quinazolinone derivatives as EGFR inhibitors for antitumor treatment

Gan

et al. 2020

Journal of Enzyme Inhibition and Medicinal Chemistry

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In this paper, a series of novel 3-methyl-quinazolinone derivatives was designed, synthesised and evaluated for antitumor activity in vitro on wild type epidermal growth factor receptor tyrosine kinase (EGFR wt -TK) and three human cancer cell lines including A549, PC-3, and SMMC-7721. The results displayed that some of the compounds had good activities, especially 2-f4-[(3-Fluoro-phenylimino)-methyl]-phenoxymethylg-3methyl-3H-quinazolin-4-one (5 g), 2-f4- [(3,-methyl]-phenoxymethylg-3-methyl-3Hquinazolin-4-one (5k) and 2-f4-[(3,5-Difluoro-phenylimino)-methyl]-phenoxymethylg-3-methyl-3H-quinazolin-4-one (5 l) showed high antitumor activities against three cancer cell lines. Moreover, compound 5k could induce late apoptosis of A549 cells at high concentrations and arrest cell cycle of A549 cells in the G2/M phase at tested concentrations. Also, compound 5k could inhibit the EGFR wt -TK with IC 50 value of 10 nM. Molecular docking data indicates that the compound 5k may exert inhibitory activity by forming stable hydrogen bonds with the R817, T830 amino acid residues and cation-P interaction with the K72 residue of EGFR wt -TK.

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“…Safavi et al . synthesized novel quinazolin‐4(3 H )‐one linked to 1,2,3‐triazoles by this procedure that a mixture of 4‐(prop‐2‐yn‐1‐yloxy) benzaldehyde derivative ( 96 ), 2‐aminobenzamide ( 95 ) and sodium metabisulfite in DMA was heated at 120 °C.…”

Section: 4‐disubstituted‐123‐triazoles As Anti‐cancer Agentsmentioning

confidence: 99%

An Overview of Recent Advances in the Applications of Click Chemistry in the Synthesis of Bioconjugates with Anticancer Activities

Mashayekh

Shiri

2019

ChemistrySelect

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The click chemistry is one of the most powerful CÀ N bond forming-reactions towards five-membered heterocycles. The copper-catalyzed azide-alkyne cycloaddition (CuAAC) has widely used in the discovery of anti-cancer drugs and many articles have been published in this field. This review article aims to review general mechanism aspects and the recent advances (2016-2019) of click chemistry for cancer therapy.

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Novel quinazolin‐4(3H)‐one linked to 1,2,3‐triazoles: Synthesis and anticancer activity

Cited by 42 publications

References 23 publications

Synthesis and cytotoxic evaluation of some derivatives of triazole-quinazolinone hybrids

Synthesis and cytotoxic evaluation of some derivatives of triazole-quinazolinone hybrids

Design, synthesis and in vitro biological evaluation of quinazolinone derivatives as EGFR inhibitors for antitumor treatment

An Overview of Recent Advances in the Applications of Click Chemistry in the Synthesis of Bioconjugates with Anticancer Activities

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