Discovery of novel 2-substituted-4-phenoxypyridine derivatives as potential antitumor agents

Duan, Yongli; Xu, Shan; Xiong, Hehua; Wang, Linxiao; Zhao, Bingbing; Wang, Ping; Wang, Caolin; Peng, Yiqing; Cai, Shifan; Luo, Rong; Zheng, Pengwu; Tang, Qidong

doi:10.1016/j.bmcl.2017.12.063

Cited by 5 publications

(2 citation statements)

References 20 publications

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“…Among all derivatives, compound 168m displayed an increase in cytotoxic activity on MIAPaCa-2 with IC 50 = 170 nM, strong inhibition of histone H3 phosphorylation, Aurora kinases A and B with IC 50 = 52, 0.3 and 0.4nM, respectively. In 2018, Duan et al [92]formed a new series of 2substituted-4-phenoxypyridine derivatives containing 1,8-naphthyridin-2-one fragment (180-206) as shown in Scheme 32 and tested for their cytotoxicity against: colon (HT-29), lung (A549, H460) and glioblastoma (U87MG) cell lines. Eleven compounds showed cytotoxicity higher than foretinib against one cancer cell line at least, but compound 200 was the most active candidate against all the cell lines under investigationand a good inhibitor for c-Met enzyme.…”

Section: 8-naphthyridines As Kinase Inhibitorsmentioning

confidence: 99%

Synthesis and Anticancer Potentials of 1,8-Naphthyridine Analogues: A Review of Literature

Ahmed¹,

Abuzahra

Sarhan

et al. 2023

Egypt. J. Chem.

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This review focuses on the potential of 1,8-Naphthyridine derivativesinchemotherapeuticcancer treatment and highlights significant recent progress in the synthetic development of 1,8-naphthyridines as antitumor agents. The present review provides the classical (Skraup, Doebner-Von-Miller, Gould-Jacob, Meth-Cohn, Friedlander, Pfitzinger, Knorr and Conard Limpach, Combes, Niementowski and Pictet-Spengler)and green approaches (metal free ionic liquid mediated reactions, microwave irradiation reactions) for 1,8-naphthyridines synthesis. Their derivatives which exert their anticancer activity via several mechanismslike apoptosis-inducing agents, cell cycle arrest, topoisomerase I and II inhibitors, tubulin polymerization inhibitors, protein kinase inhibitors, intercalation with DNA, angiogenesis inhibitors, Ras protein inhibitors and telomerase inhibitors, are highlighted with proper synthetic methods, SAR studies and molecular docking of these derivatives.

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Section: 8-naphthyridines As Kinase Inhibitorsmentioning

confidence: 99%

Synthesis and Anticancer Potentials of 1,8-Naphthyridine Analogues: A Review of Literature

Ahmed¹,

Abuzahra

Sarhan

et al. 2023

Egypt. J. Chem.

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“…The structure–activity relationships (SARs) showed that the urea moiety of sorafenib derivates was replaced with other scaffolds containing hydrogen‐bond donors and acceptors such as cyclopropane‐1,1‐dicarboxamide, 2‐oxo‐1,2‐dihydro‐1,8‐naphthyridine‐3‐carboxamide, chalcone, pyrimidine‐4‐carboxamide, pyrazole, sulfonylurea, and 3‐oxo‐1 H ‐pyrazole‐4‐carboxamide and also exhibited excellent antitumor activity (compound 3 , 5 – 10 in Figure ). Inspired by these compounds and with the goal of finding more antitumor agents, we replaced the urea moiety of sorafenib with 4‐oxo‐1,4‐dihydropyridazine‐3‐carboxamide scaffold in this paper.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, and biological evaluation of novel 4‐phenoxypyridine derivatives as potential antitumor agents

Liu

Hao

et al. 2019

Archiv der Pharmazie

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A series of novel 4‐phenoxypyridine derivatives containing the 4‐oxo‐1,4‐dihydropyridazine‐3‐carboxamide moiety were synthesized and evaluated for their in vitro cytotoxic activity against the A549 cancer cell line, and some compounds were further examined for their cytotoxic activity against the H460, BGC823, MKN45, and HT‐29 cancer cell lines. Most of the compounds exhibited moderate to significant cytotoxicity. The most promising compound 15b (with VEGFR2 inhibitory concentration [IC50] value of 0.23 μM) showed remarkable cytotoxicity against A549, BGC‐823, MKN45, H460, and HT‐29 cells, with IC50 values of 0.75, 1.68, 2.63, 5.08 and 7.22 μM, respectively. Their preliminary structure‐activity relationship studies indicate that electron‐withdrawing groups on the terminal phenyl rings are beneficial for improving the antitumor activity. Moreover, treatment of A549 cells with compound 15b resulted in cell cycle arrest in the G0/G1 phase in a dose‐dependent manner. Further apoptotic studies and acridine orange/ethidium bromide staining were also performed on A549 cells, which showed that compound 15b could induce apoptosis. Wound‐healing assay results indicated that compound 15b strongly inhibited A549 cell motility.

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Novel ferrocenylbisphosphonate hybrid compounds: Synthesis, characterization and potent activity against cancer cell lines

Anusionwu

Aderibigbe

Adeyemi

et al. 2022

Bioorganic & Medicinal Chemistry

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Discovery of novel 2-substituted-4-phenoxypyridine derivatives as potential antitumor agents

Cited by 5 publications

References 20 publications

Synthesis and Anticancer Potentials of 1,8-Naphthyridine Analogues: A Review of Literature

Synthesis and Anticancer Potentials of 1,8-Naphthyridine Analogues: A Review of Literature

Design, synthesis, and biological evaluation of novel 4‐phenoxypyridine derivatives as potential antitumor agents

Novel ferrocenylbisphosphonate hybrid compounds: Synthesis, characterization and potent activity against cancer cell lines

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