Design, synthesis and anticancer evaluation of 6,7-disubstituted-4-phenoxyquinoline derivatives bearing 1,8-naphthyridine-3-carboxamide moiety as novel multi-target TKIs

Chen, Pengqin; Zhao, Ying; Duan, Yongli; Dai, Jintian; He, Jie; Wang, Xiemin; Chen, Xi; Pan, Chaoyun; Zhao, Weixin; Zhuang, Zaishou; Yang, Daona; Liang, Guang; Tang, Qidong

doi:10.1016/j.bioorg.2022.105672

Cited by 6 publications

(8 citation statements)

References 34 publications

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“…The spectroscopic data are consistent with those previously reported. 24 TLC: R f = 0.48 (EA). 1 H NMR (400 MHz, DMSO-d 6 ) δ 14.50 (s, 1H), 8.91 (s, 1H), 8.87 (dd, J = 1.6 Hz, 4.4 Hz, 1H), 8.80 (dd, J = 1.6 Hz, 7.6 Hz, 1H), 7.70−7.75 (m, 3H), 7.44− 7.48 (m, 2H).…”

Section: Tert-butyl 1-(4-methoxyphenyl)-4-oxo-14-dihydro-18-naphthyri...mentioning

confidence: 99%

“…The spectroscopic data are consistent with those previously reported. 24 TLC: R f = 0.52 (EA). 1 H NMR (600 MHz, DMSO-d 6 ) δ 14.56 (s, 1H), 8.88 (dd, J = 1.8 Hz, 4.2 Hz, 1H), 8.84 (s, 1H), 8.80 (dd, J = 1.8 Hz, 8.4 Hz, 1H), 7.73 (dd, J = 4.2 Hz, 7.8 Hz, 1H), 7.55 (d, J = 9.0 Hz, 2H), 7.14 (d, J = 9.0 Hz, 2H), 3.86 (s, 3H).…”

Section: Tert-butyl 1-(4-methoxyphenyl)-4-oxo-14-dihydro-18-naphthyri...mentioning

confidence: 99%

“…The spectroscopic data are consistent with those previously reported. 24 TLC: R f = 0.46 (EA). 1-Cyclopropyl-5-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3carboxylic Acid (1ba).…”

Section: Tert-butyl 1-(4-methoxyphenyl)-4-oxo-14-dihydro-18-naphthyri...mentioning

confidence: 99%

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Accessing 1,8-Naphthyridone-3-carboxylic Acid Derivatives and Application to the Synthesis of Amfonelic Acid

Wang,

Gong,

Xiao

et al. 2024

J. Org. Chem.

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Naphthyridone-3-carboxyl is the core structure of several on-market antibacterial drugs. It has prompted significant interest from the synthetic community. Here, we report a practical synthesis of diversely functionalized 1,8-naphthyridone-3-carboxylic acid derivatives starting from readily available and inexpensive nicotinic acid derivatives. All key steps have been optimized. Furthermore, the usefulness of this protocol has been exemplified by the first synthesis of amfonelic acid.

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Section: Tert-butyl 1-(4-methoxyphenyl)-4-oxo-14-dihydro-18-naphthyri...mentioning

confidence: 99%

Section: Tert-butyl 1-(4-methoxyphenyl)-4-oxo-14-dihydro-18-naphthyri...mentioning

confidence: 99%

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Accessing 1,8-Naphthyridone-3-carboxylic Acid Derivatives and Application to the Synthesis of Amfonelic Acid

Wang,

Gong,

Xiao

et al. 2024

J. Org. Chem.

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“…[ 7 ] Targeting TKs using TK inhibitors (TKIs) is very useful anticancer therapeutic strategy. [ 8,9 ] For instance, gefitinib is an EGFR inhibitor used to treat non‐small cell lung cancer; however, it shows little activity against HER2‐overexpressing cancers such as breast cancer. [ 10 ] Recently, targeted cancer therapies have focused on EGFR and HER2 inhibitors.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel pyrimido[4,5‐b]quinoline derivatives as dual EGFR/HER2 inhibitors as anticancer agents

Ibrahim,

Kadry,

Zaher

et al. 2023

Archiv der Pharmazie

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A series of novel N‐aryl‐5‐aryl‐6,7,8,9‐tetrahydropyrimido[4,5‐b]quinolin‐4‐amines 4a–4l was synthesized as potential anticancer agents through Dimroth rearrangement reaction of intermediates 3a–3c. Pyrimido[4,5‐b]quinolines 4a–4l showed promising activity against the Michigan Cancer Foundation‐7 (MCF‐7) cell line, compared with lapatinib as the reference drug. Compounds 4d, 4h, 4i, and 4l demonstrated higher cytotoxic activity than lapatinib, with IC50 values of 2.67, 6.82, 4.31, and 1.62 µM, respectively. Compounds 4d, 4i, and 4l showed promising epidermal growth factor receptor (EGFR) inhibition with IC50 values of 0.065, 0.116, and 0.052 µM, respectively. These compounds were subjected to human epidermal growth factor receptor 2 (HER2) inhibition and showed IC50 values of 0.09, 0.164, and 0.055 µM, respectively. Compounds 4d, 4i, and 4l are good candidates as dual EGFR/HER2 inhibitors. The most active compound, 4l, was subjected to cell‐cycle analysis and induced cell‐cycle arrest at the S phase. Compound 4l induced apoptosis 60‐fold compared with control untreated MCF‐7 cells. 4l can inhibit cancer metastasis. It reduced MCF‐7 cell infiltration and metastasis by 45% compared with control untreated cells.

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“…With the development of cytobiology and molecular biology, the essential principles of tumorigenesis, invasion, migration, and metastasis induced by quinoline derivatives have been further explained. Antitumor mechanisms of quinoline derivatives include alkylating DNA [ 14 ], inhibiting c-Met kinase [ 15 ], epidermal growth factor receptor (EGFR) [ 16 ], and vascular endothelial growth factor (VEGF) [ 16 , 17 , 18 ]. Some were also proven to inhibit P-glycoprotein [ 19 ].…”

Section: Introductionmentioning

confidence: 99%

The Anticancer Effect of a Novel Quinoline Derivative 91b1 through Downregulation of Lumican

Zhou

Chan

et al. 2022

IJMS

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Quinoline derivatives have been reported to possess a wide range of pharmaceutical activities. Our group previously synthesized a series of quinoline compounds, in which compound 91b1 showed a significant anticancer effect. The purpose of this study was to evaluate the anticancer activity of compound 91b1 in vitro and in vivo, and screen out its regulated target. A series of cancer cell lines and nontumor cell lines were treated with compound 91b1 by MTS cytotoxicity assay and cell-cycle assay. In vivo anticancer activity was evaluated by a xenografted model on nude mice. Target prediction of 91b1 was assessed by microarray assay and confirmed by pancancer analysis. Relative expression of the target gene Lumican was measured by qRT-PCR. 91b1 significantly reduced tumor size in the nude mice xenograft model. Lumican was downregulated after 91b1 treatment. Lumican was proven to increase tumorigenesis in vivo, as well as cancer cell migration, invasion, and proliferation in vitro. The results of this study suggest that the anticancer activity of compound 91b1 probably works through downregulating the gene Lumican.

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Design, synthesis and anticancer evaluation of 6,7-disubstituted-4-phenoxyquinoline derivatives bearing 1,8-naphthyridine-3-carboxamide moiety as novel multi-target TKIs

Cited by 6 publications

References 34 publications

Accessing 1,8-Naphthyridone-3-carboxylic Acid Derivatives and Application to the Synthesis of Amfonelic Acid

Accessing 1,8-Naphthyridone-3-carboxylic Acid Derivatives and Application to the Synthesis of Amfonelic Acid

Synthesis of novel pyrimido[4,5‐b]quinoline derivatives as dual EGFR/HER2 inhibitors as anticancer agents

The Anticancer Effect of a Novel Quinoline Derivative 91b1 through Downregulation of Lumican

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