Design, synthesis and biological activities of novel oxazolo[4,5- g ]quinazolin-2(1H)-one derivatives as EGFR inhibitors

Yin, Shuai; Zhou, Liliang; Lin, Jinsheng; Xue, Lingjing; Zhang, Can

doi:10.1016/j.ejmech.2015.07.008

Cited by 30 publications

(9 citation statements)

References 20 publications

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“…The search for novel potent derivatives as next‐generation EGFR kinase will subside such challenges. Different quinazoline and quinazolinone scaffolds as VEGFR and Dual EGFR/VEGFR inhibitor come out very promising (Alnoman et al, 2022; Ansari et al, 2019; Banerji et al, 2018; Eissa et al, 2021; El‐azab et al, 2017; Le et al, 2020; Mowafy et al, 2016; Yin, Sha, et al, 2015). Most of the reported compounds have exhibited inhibitory activity similar to vandetanib and cediranib.…”

Section: Discussion and Future Perspectivementioning

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: Discussion and Future Perspectivementioning

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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“…Around 60% of the medications used for cancer treatment are based on heterocyclic moieties [13]. Heterocyclic compounds like pyrimidine [16][17][18][19][20][21][22], phthalazine [23], benzothiazole [24], Benzpyrazoline [25,26], indoline [27][28][29][30][31], benzimidazole [32], phthalazone [33], indole [34,35], quinoline [36,37], quinazoline [38] find application in the treatment of renal cancer. Many synthetic nitrogen heterocycles are extremely relevant to pharmacology and medicine.…”

Section: Introductionmentioning

confidence: 99%

ADMET Prediction of synthesized Heterocyclic derivatives to treat renal cancer

Cordeiro¹,

Khan²,

Tajir³

et al. 2022

German J. Pharm. Biomaterials

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A library of 121 potent, synthesized, and characterized compounds from different heterocyclic derivatives such as pyrimidine, phthalazine, benzothiazole, benzpyrazoline, indoline, benzimidazole, phthalazine, indole, quinoline, quinazoline were selected based on their anti-renal cancer activity. The Drug likeness, Bioactivity, Absorption, Distribution, Metabolism, Excretion, and Toxicity of all the screened compounds were predicted through Molinspiration, PreADMET, and Osiris software. After screening 121 compounds, 19 compounds showed drug-like properties and an absorption percentage better than the standard drug Sorafenib. These compounds were further assessed based on their distribution parameter and the compounds that showed plasma protein binding equal to or below 90% and blood-brain barrier penetration below 1.000 were selected, i.e., compounds 3, 23, 64, 65 were then further assessed for the toxicity. Osiris property explorer was used to predict drug relevance and toxicity of the synthesized compounds. Compounds 3 and 23 were non-toxic similar to the standard drug Sorafenib. Compounds 3 and 23 were found to be active as Kinase Inhibitors, with a bioactivity score of 0.2 and 0.6 compared to standard drug sorafenib, which scored 0.44. Therefore Compound 3 N-(4-fluoro-2-methoxyphenyl)-7-methyl-5,6,7,8tetrahydropyrido [4',3':4,5] thieno[2,3-d] pyrimidin-4-amine and compound 23 1-(4-fluorophenyl)-3methyl-N-phenyl-3a,7a-dihydro-1H-pyrazolo [3,4-d] pyrimidin-4-amine belonging to pyrimidine derivatives were considered as best and suggested to be taken further for preclinical and clinical trials. The pyrimidine derivatives with anti-renal cancer activity can serve as a scaffold for the design of renal cancer targeting agents and motivates the further development of effective and safer compounds.

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“…It was found to be most well known synthetic quinazolinone drug, prominent for its sedative-hypnotic activity. 4 Quinazolinone nucleus has attracted much interest because of a wide range of pharmacological activites like antitumor, [5][6][7] anticonvulsant, 8 antitubercular, 9,10 antiviral, 11 anti-inflammatory, 12 analgesics, 13 antimicrobial, 14 antihypertensive, 15 antioxidant 16 activities etc (Figure 4). Recently quinazolinone chemistry has got new direction due to some resemblance with folic acid.…”

Section: Introductionmentioning

confidence: 99%

Chemistry and activity of quinazoline moiety: A systematic review study

Negi¹,

Bisht²,

Sharma³

2020

IJPCA

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Quinazoline is a compound with amalgamated heterocyclic system popular for their biological activities. Quinazoline is a compound made up six membered fused aromatic rings i,e a benzene ring with pyrimidine ring. Its chemical formula is CHNO. It is yellow colour and found in the crystalline form. Molecular optimization of potentially lead compounds through a chemist is an needy and upcomming approach for the discovery of new pharmaceuticals. More than two combinations of pharmacophore and making them one moiety is a noval and popular procedure of exploitation of synthesis now a days and this cause an additive increment of biological activities with taking away of surplus side effects. Present communication studies about the structure origin, diversity and chemical modification with change in pharmacological activities of Quinazoline.

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Design, synthesis and biological activities of novel oxazolo[4,5- g ]quinazolin-2(1H)-one derivatives as EGFR inhibitors

Cited by 30 publications

References 20 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

ADMET Prediction of synthesized Heterocyclic derivatives to treat renal cancer

Chemistry and activity of quinazoline moiety: A systematic review study

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