Synthesis of chalcone incorporated quinazoline derivatives as anticancer agents

Madhavi, Sapavat; Sreenivasulu, Reddymasu; Yazala, Jyothsna Pragathi; Raju, Rudraraju Ramesh

doi:10.1016/j.jsps.2016.06.005

Cited by 86 publications

(30 citation statements)

References 24 publications

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“…Quinazoline derivatives are known as potent inhibitors of the epidermal growth factor receptors (EGFRs) of tyrosine kinase as a class of nitrogen‐containing heterocyclic compounds . Quinazoline derivatives have illustrated important anti‐cancer activities …”

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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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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“…Most of the advanced materials [17][18][19][20][21][22] and heterocyclic compounds [23][24][25][26] play a vital role in medicinal chemistry as well as industrial field and exhibited potent antitumor activities against different human cancer cell lines. The pyrazole scaffolds belong to a highly important class of heterocyclic compounds which have attracted much attention for their significant bioactivity.…”

Section: Introductionmentioning

confidence: 99%

Novel Pyrazolyl Benzoxazole Conjugates: Design, Synthesis, Molecular Docking Studies and in vitro Anticancer Activities

Thiriveedhi

Nadh

Srinivasu

et al. 2019

LOC

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Nowadays, hybrid drugs have gained a significant role in the treatment of different health problems. Most of the hybrid molecules with different heterocyclic moieties were proved to be potent anti-tumor agents in cancer chemotherapy. Hence, the present study is aimed at the evaluation of in vitro anticancer activity of novel hybrid molecules (pyrazolyl benzoxazole conjugates) and to investigate their anticancer activity by molecular docking studies. Designed, synthesized and characterized the novel pyrazolyl benzoxazole conjugates. Anticancer activity of these compounds was determined by SRB assay. Then molecular docking studies were carried out against proto-oncogene tyrosine-protein kinase (ATP-Src, PDB: 2BDF), a putative target for cancer. All the synthesized compound derivatives were evaluated against MCF-7, KB, Hop62 and A549 cancer cell lines. Compounds 9b and 9c exhibited excellent anticancer activities with GI50 values of <0.1 µM against MCF-7 and A549 cell lines. Compound 9e exhibited good antitumor activity on MCF-7 and A-549 with GI50 values of 0.12 µM and 0.19 µM respectively. Compound 9g showed better anticancer activity on A-549 cancer cell line with GI50 of 0.34 µM. The two-hybrid molecules 9b and 9c are found to be comparably potent with the standard drug doxorubicin and may act as drug lead compounds in medicinal chemistry aspect. The present docking investigation proved that having benzoxazole of compound 9c at the position of benzofuran of reference compound (N-acetyl pyrazoline derivative) might be valid for contributing to anti-cancer activity.

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“…Quinazoline derivatives have a wide spectrum of biological properties, which allow their use in the production of antiinflammatory [6], anti-parasitic [7], anti-histamine [8], antidiuretic [9], and anti-cancer [10] drugs. In turn, imidazoquinazoline derivatives have wide application in medicine and pharmacy due to their anti-tumor, anti-viral, antibacterial or anti-convulsive, and anti-oxidative activity [11][12][13][14][15][16].…”

Section: Introductionmentioning

confidence: 99%

Unprecedented reaction course of 1-phenyl-2H,6H-imidazo[1,5-c]quinazoline-3,5-dione with 3-M excess of ethylene oxide

et al. 2019

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The reaction of 1-phenyl-2H,6H-imidazo[1,5-c]quinazolino-3,5-dione (4) with 3-molar excess ethylene oxide was described. The resulting product was characterized by spectroscopic techniques (1 H-, 13 C-NMR, IR, and UV) and by X-ray crystallography. It was expected to produce a product of the subsequent reaction in the hydroxyl groups of the initially formed diol-1-phenyl-2,6-bis(2-hydroxyethyl)imidazo[1,5-c]quinazoline-3,5-dione (7) with ethylene oxide (5). However, crystallographic studies revealed that the proper and only product of the reaction is 3-{2-[1,3-bis(2hydroxyethyl)-2-oxo-4-phenylimidazolidin-5-yl]phenyl}-1,3-oxazolidin-2-one (8). This product was formed by quinazoline ring opening which occurred in the presence of more than 2-molar excess ethylene oxide. In the work, the exemplary reaction mechanism explaining the formation of the unexpected product was proposed. In order to understand the reasons of quinazoline ring opening, the quantum mechanical modeling was performed. Energy of transition states indicated that the reaction with the third mole of ethylene oxide was controlled by kinetics.

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Synthesis of chalcone incorporated quinazoline derivatives as anticancer agents

Cited by 86 publications

References 24 publications

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

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

Novel Pyrazolyl Benzoxazole Conjugates: Design, Synthesis, Molecular Docking Studies and in vitro Anticancer Activities

Unprecedented reaction course of 1-phenyl-2H,6H-imidazo[1,5-c]quinazoline-3,5-dione with 3-M excess of ethylene oxide

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