New acrylamide-substituted quinazoline derivatives with enhanced potency for the treatment of EGFR T790M-mutant non-small-cell lung cancers

Liu, Zhuo; Wang, Luhong; Feng, Min; Yi, Yuanyuan; Zhang, Wenhan; Liu, Wenjuan; Li, Lei; Liu, Zhihao; Li, Yanxia; Ma, Xiaodong

doi:10.1016/j.bioorg.2018.01.035

Cited by 17 publications

(4 citation statements)

References 26 publications

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“…Z. Liu et al (2018) have developed novel acrylamide substituted quinazoline derivatives as potent EGFR kinase inhibitors. All the synthesized derivatives are evaluated against wild-type EGFR and mutant EGFR T790M .…”

Section: Egfr Inhibitorsmentioning

confidence: 99%

An appraisal of anticancer activity with structure–activity relationship of quinazoline and quinazolinone analogues through EGFR and VEGFR inhibition: A review

Haider

Das

Joseph

et al. 2022

Drug Development Research

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Cancer is one of the leading causes of death. Globally a huge number of deaths and new incidences are reported annually. Heterocyclic compounds have been proved to be very effective in the treatment of different types of cancer. Among different heterocyclic scaffolds, quinazoline and quinazolinone core were found versatile and interesting with many biological activities. In the discovery of novel anticancer agents, the Quinazoline core is very effective. The FDA has approved more than 20 drugs as an anticancer bearing quinazoline or quinazolinone core in the last two decades. One prime example is Dacomitinib, which was newly approved for non-small-cell lung carcinoma treatment in 2018. These drugs work by different pathways to prevent the spread of cancer cell progression, including inhibition of different kinases, tubulin, kinesin spindle protein, and so forth. This review presented recent developments of quinazoline/quinazolinone scaffold bearing derivatives as anticancer agents acting as epidermal growth factor receptor (EGFR) vascular endothelial growth factor receptor (VEGFR), and dual EGFR/VEGFR inhibitors.

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Section: Egfr Inhibitorsmentioning

confidence: 99%

An appraisal of anticancer activity with structure–activity relationship of quinazoline and quinazolinone analogues through EGFR and VEGFR inhibition: A review

Haider

Das

Joseph

et al. 2022

Drug Development Research

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“…Song et al to improve the selectivity of EGFR mutations synthesized a few triazole-linked quinazoline derivatives from quinazoline-based kinase inhibitors by click chemistry. The compound synthesized was evaluated for kinase inhibition assay showed that compound D7 (Figure 8) with IC 50 of 4 nM (EGFR L858R/T790M ), anti-proliferative activity with IC 50 of 505 nM in H1975 cell line and 0.9 nM in PC9 cell lines respectively ( T A B L E 4 Biological evaluation of quinazoline derivatives (Liu et al, 2018;Pawara et al, 2021;Qin et al, 2016;Song et al, 2019;Wang et al, 2016;Zhang et al, , 2021 D10 AND D11 (Figure 8) had an IC 50 value of 0.880 and 0.336 μM (Table 4). Docking data revealed good binding interaction by compound D11 but not as effective as gefitinib (Qin et al, 2016).…”

Section: Quinazoline Derivativesmentioning

confidence: 99%

“…For improving the EGFR T790M inhibitory action, Lui et al designed and synthesized a group of quinazoline derivatives referencing gefitinib and erlotinib, in which biological evaluation identified compound D9 (Figure 8) having IC 50 = 4.3 nM in EGFR L858R/T790M kinase assay and cellular assay with IC 50 values of 8.70, 13.45, 0.65, and 32.42 μM in H1975, A431, HCC827, and A549 cell lines (Table 4). Docking analysis observed the binding interaction by the formation of covalent and hydrogen bonds acrylamide group and quinazoline core moieties (Liu et al, 2018). Qin et al synthesized a group of fused quinazoline analogs and assessed them for kinase inhibition activity.…”

Section: Quinazoline Derivativesmentioning

confidence: 99%

Pyrimidine derivatives as EGFR tyrosine kinase inhibitors in non‐small‐cell lung cancer: A comprehensive review

et al. 2022

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EGFR-positive non-small-cell lung cancer (NSCLC) due to primary mutation (EGFR DEL19 & L858R) has been recognized as a crucial mediator of tumor progression. This led to the development and approval of EGFR tyrosine kinase inhibitors, which addresses EGFR-mediated NSCLC but fail to show potency after initial months of therapy due to acquired resistance (EGFR T790M, EGFR C797S). Extensive research allowed identification of drugs for EGFR-positive NSCLC, wherein the majority of compounds have a pyrimidine substructure offering marked therapeutic benefits compared with chemotherapy. This current review outlines the diverse pyrimidine derivatives with amino-linked and fused pyrimidine scaffolds such as furo-pyrimidine, pyrimido-pyrimidine, thienopyrimidine, highlighting pyrimidine EGFR TK inhibitors reported in research emphasizing structural aspects, design approaches, inhibition potential, selectivity profile toward mutant EGFR conveyed through biological evaluation studies.Furthermore, mentioning the in-silico interaction profile of synthesized compounds for evaluating the binding affinity with key amino acids. The epilogue of review focuses on the recent research that drives forward to aid in the discovery and development of substituted amino and fused scaffolds of pyrimidine that can counteract the mutations and effectively manage EGFR-positive NSCLC.

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“…Additionally, the unique photochromic behavior of quinazoline scaffolds has been exploited to elucidate cellular signaling processes of epidermal growth factor receptor ( Liu et al, 2018 ) (EFGR) and α 1 -adrenergic receptors ( Ma et al, 2016 ). Furthermore, quinazolines have been identified as light-emitting materials for electronic devices ( Lipunova et al, 2018 ).…”

Section: Introductionmentioning

confidence: 99%

Transition-metal-catalyzed synthesis of quinazolines: A review

2023

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Quinazolines are a class of nitrogen-containing heterocyclic compounds with broad-spectrum of pharmacological activities. Transition-metal-catalyzed reactions have emerged as reliable and indispensable tools for the synthesis of pharmaceuticals. These reactions provide new entries into pharmaceutical ingredients of continuously increasing complexity, and catalysis with these metals has streamlined the synthesis of several marketed drugs. The last few decades have witnessed a tremendous outburst of transition-metal-catalyzed reactions for the construction of quinazoline scaffolds. In this review, the progress achieved in the synthesis of quinazolines under transition metal-catalyzed conditions are summarized and reports from 2010 to date are covered. This is presented along with the mechanistic insights of each representative methodology. The advantages, limitations, and future perspectives of synthesis of quinazolines through such reactions are also discussed.

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New acrylamide-substituted quinazoline derivatives with enhanced potency for the treatment of EGFR T790M-mutant non-small-cell lung cancers

Cited by 17 publications

References 26 publications

An appraisal of anticancer activity with structure–activity relationship of quinazoline and quinazolinone analogues through EGFR and VEGFR inhibition: A review

An appraisal of anticancer activity with structure–activity relationship of quinazoline and quinazolinone analogues through EGFR and VEGFR inhibition: A review

Pyrimidine derivatives as EGFR tyrosine kinase inhibitors in non‐small‐cell lung cancer: A comprehensive review

Transition-metal-catalyzed synthesis of quinazolines: A review

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