Direct one-pot synthesis of 3-nitroquinolin-2(1H)-one via H2O/AcOH system: An improvement to classical Friedlander reaction

Chen, Xinfei; Ren, Chao; Xu, Xiaoyong; Shao, Xusheng; Li, Zhong

doi:10.1016/j.tetlet.2017.01.092

Cited by 11 publications

(3 citation statements)

References 25 publications

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“…2-(2-Fluorophenyl)-3-aminoquinoline was synthesized according to the method described in previous reports. ,− 2-(2-Fluorophenyl)-3-aminoquinoline (238 mg, 1 mmol) and various 2-hydroxybenzaladehyde derivatives (1.1 mmol) were dissolved in CH 3 OH and stirred at 80 °C for 5–12 h, respectively. The H-L 1 –H-L 12 were obtained by cooling, filtering, and further recrystallization in CH 3 OH.…”

Section: Methodsmentioning

confidence: 99%

Copper(II) Complexes of Halogenated Quinoline Schiff Base Derivatives Enabled Cancer Therapy through Glutathione-Assisted Chemodynamic Therapy and Inhibition of Autophagy Flux

et al. 2022

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Twelve new complexes Cu(L1)2 –Cu(L12)2 were designed and synthesized to improve their chemotherapeutic properties. They showed considerable antiproliferative activity against T24 cancer cells but lower cytotoxicity to human normal cells HL-7702 and WI-38. A mechanism study indicated that Cu(L4)2 and Cu(L10)2 were reduced to Fenton-like Cu+ by glutathione depletion, and the resulting Cu+ catalyzed the generation of highly toxic hydroxyl radicals from excess H2O2. Simultaneously, Cu(L4)2 and Cu(L10)2 could decrease the catalase activity to restrain H2O2 transfer to H2O for enhanced chemodynamic therapy (CDT). These induced mitochondrial dysfunctions and endoplasmic reticulum stress to induce T24 cell apoptosis. In addition, Cu(L4)2 and Cu(L10)2 inhibited autophagy flux to promote cell apoptosis. Cu(L4)2 and Cu(L10)2 demonstrated strong tumor inhibition ability in the T24 xenograft model. Moreover, Cu(L10)2 showed higher antitumor activity and a better safety profile than the CDT agent Cu1. Cu(L10)2 exhibited excellent pharmacokinetic properties. Collectively, Cu(L4)2 and Cu(L10)2 could be developed as potential CDT candidates for cancer treatment.

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Section: Methodsmentioning

confidence: 99%

Copper(II) Complexes of Halogenated Quinoline Schiff Base Derivatives Enabled Cancer Therapy through Glutathione-Assisted Chemodynamic Therapy and Inhibition of Autophagy Flux

et al. 2022

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“…2-(2-Fluorophenyl)-3-aminoquinoline was obtained according to the steps reported in the references. 34–37 Then 2-(2-fluorophenyl)-3-aminoquinoline and 2-hydroxybenzaladehyde derivatives were dissolved in CH 3 OH by continuously stirring at 80 °C for 5–12 h. The product quinolone ligand was obtained by cooling, filtering, and further recrystallizing with CH 3 OH.…”

Section: Methodsmentioning

confidence: 99%

“…2-(2-Fluorophenyl)-3-aminoquinoline was obtained according to the steps reported in the references. [34][35][36][37] 8.09 (t, J = 1.5 Hz, 2H), 7.90 (s, 1H), 7.83 (ddd, J = 8.4, 6.9, 1.5 Hz, 1H), 7.71 (ddd, J = 8.2, 6.9, 1.2 Hz, 1H), 7.66-7.58 (m, 2H), 7.57 (ddd, J = 9.9, 4.9, 2.1 Hz, 2H), 7.41-7.29 (m, 2H), 7.24 (d, J = 2.8 Hz, 1H). 13…”

Section: Methodsmentioning

confidence: 99%