Synthesis of 1-substituted 3-pyridinylmethylidenylindolin-2-ones and 1-substituted 3-quinolinylmethylidenylindolin-2-ones as the enhancers of ATRA-induced differentiation in HL-60 cells

Hung, Chi-Ying; Hsu, Mei‐Hua; Huang, Li‐Jiau; Hwang, Chrong-Shiong; Lee, On; Wu, Chen‐Yi; Chen, Chih‐Hung; Kuo, Sheng‐Chu

doi:10.1016/j.bmc.2008.02.093

Cited by 12 publications

(3 citation statements)

References 11 publications

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“…All-trans retinoic acid, a derivative of vitamin A, exhibits great effects on cell differentiation (Chen et al, 2009;Congleton et al, 2011;Hung et al, 2008). In acute promyelocytic leukemia (APL), ATRA is a potent inducer of APL cell differentiation.…”

Section: Introductionmentioning

confidence: 99%

The synergistic antitumor effects of all-trans retinoic acid and C-phycocyanin on the lung cancer A549 cells in vitro and in vivo

Gao

Chu

et al. 2015

European Journal of Pharmacology

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Section: Introductionmentioning

confidence: 99%

The synergistic antitumor effects of all-trans retinoic acid and C-phycocyanin on the lung cancer A549 cells in vitro and in vivo

Gao

Chu

et al. 2015

European Journal of Pharmacology

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“…The isatin molecule (1H-indole-2,3-dione) is a versatile moiety that displays diverse biological activities, including anticancer activity (Pandeya et al, 1999;Cane et al, 2000;Torres et al, 2004;Pandeya et al, 2005;Abadi et al, 2006;Vine et al, 2007a, b;Uddin et al, 2007;Hung et al, 2008;González et al, 2009;Sirisoma et al, 2009). The synthetic flexibility of isatin led to synthesis of a variety of substituted derivatives; however, the susceptibility of isatin to attack by nucleophiles at C3 resulted in the generation of a large number of 3-substituted isatins in particular (Bramson et al, 2001;Andreani et al, 2005;Chen et al, 2005).…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, and QSAR study of novel 2-(2,3-dioxo-2,3-dihydro-1H-indol-1-yl)-N-phenylacetamide derivatives as cytotoxic agents

Modi¹,

Shah

Patel

et al. 2010

Med Chem Res

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This study deals with the synthesis of novel 2-(2,3-dioxo-2,3-dihydro-1H-indol-1-yl)-N-phenylacetamide derivatives (6a-j) from isatin (3) and 5,7-dibromoisatin (4). All newly synthesized compounds were characterized using IR, 1 H NMR, MS, and elemental analysis followed by evaluation of their cytotoxic activity by XTT assay on breast cancer cell line MCF-7 and non-cancer African green monkey cell line VERO. Correlation study for QSAR and in vitro assay was performed. The outcomes indicated that electron withdrawing substitutions at para position of phenyl ring and 5, 7 positions of isatin ring and increasing lipophilicity of the compound increased the cytotoxic activity. The 2-(5,7-dibromo-2,3-dioxo-2,3-dihydro-1H-indol-1-yl)-N-(4-nitrophenyl)acetamide (6b) was found to be the most active compound in the series and demonstrated higher selectivity toward MCF-7 cell line. The IC 50 values were 1.96 and 1.90 lM for test compound (6b) and vinblastin (reference drug), respectively. This indicates compound (6b) may possess equipotent cytotoxic activity to vinblastine. The compound (6b) is particularly promising, since it could kill cancer cells 19-20 times more effectively than the non-cancer cells. This property of (6b) may enable us to effectively control tumors with low side effects. Hence, we propose that 2-(5,7-dibromo-2,3-dioxo-2,3-dihydro-1H-indol-1-yl)-N-(4-nitrophenyl)acetamide may be used as lead for further development.

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“…H‐2′ and H‐6′ of 2g display a down‐field shift (8.51 ppm) in the Z ‐isomer than E ‐isomer (7.79 ppm) due to the deshielding effect of the carbonyl group at the 2‐position of indole ring. The signals from H‐4 of E ‐isomers of 2g and 6c (7.87 and 7.60 ppm) were markedly shifted upfield relative to the H‐4 signals of Z ‐isomers 2g and 6c (8.02 and 7.74 ppm) due to the shielding effect of H‐2′ and H‐6′ of benzylidene substituent . For the imine derivatives, the E ‐isomer was assigned to the major isomer because of the chemical shifts of H‐4 and NOE correlation between H‐4 and H‐2′/H‐6′.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Biological, and Computational Evaluation of Novel 1,3,5‐Substituted Indolin‐2‐one Derivatives as Inhibitors of Src Tyrosine Kinase

Kılıç-Kurt

Bakar

Ölgen

2015

Archiv der Pharmazie

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Several substituted indolin-2-one derivatives were synthesized and evaluated for their activities against Src kinase. Several compounds showed activity against Src, with IC50 values in the low micromolar range. Among them, compound 2f showed the most significant activity with an IC50 value of 1.02 μM. Molecular docking studies have been performed for evaluation of the binding modes of compound 2f into the Src active site. The docking structure of compound 2f disclosed that the indole NH forms a hydrogen bond with the carbonyl of Met341. These results suggest that our novel compound 2f is a promising compound for the further development of indole-based drugs targeting Src kinase.

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Synthesis of 1-substituted 3-pyridinylmethylidenylindolin-2-ones and 1-substituted 3-quinolinylmethylidenylindolin-2-ones as the enhancers of ATRA-induced differentiation in HL-60 cells

Cited by 12 publications

References 11 publications

The synergistic antitumor effects of all-trans retinoic acid and C-phycocyanin on the lung cancer A549 cells in vitro and in vivo

The synergistic antitumor effects of all-trans retinoic acid and C-phycocyanin on the lung cancer A549 cells in vitro and in vivo

Design, synthesis, and QSAR study of novel 2-(2,3-dioxo-2,3-dihydro-1H-indol-1-yl)-N-phenylacetamide derivatives as cytotoxic agents

Synthesis, Biological, and Computational Evaluation of Novel 1,3,5‐Substituted Indolin‐2‐one Derivatives as Inhibitors of Src Tyrosine Kinase

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