1677-37-8Relevant articles and documents
Efficient chemoselective alkylation of quinoline 2,4-diol derivatives in water
Ahmed, Nafees,Brahmbhatt, Keyur G.,Singh, Inder P.,Bhutani, Kamlesh K.
, p. 237 - 240 (2011)
Synthesis of various C-3-dialkyl derivatives of quinoline 2,4-diol was achieved by condensation of aniline or substituted anilines with diethyl malonate, followed by chemoselective alkylation at C-3 in water. The higher yields, easy work up and environmental compatible conditions are the main aspects of our method.
Synthesis and SAR studies of novel 6,7,8-substituted 4-substituted benzyloxyquinolin-2(1H)-one derivatives for anticancer activity
Chen, Yi-Fong,Lin, Yi-Chien,Morris-Natschke, Susan L.,Wei, Chen-Fang,Shen, Ting-Chen,Lin, Hui-Yi,Hsu, Mei-Hua,Chou, Li-Chen,Zhao, Yu,Kuo, Sheng-Chu,Lee, Kuo-Hsiung,Huang, Li-Jiau
, p. 1195 - 1221 (2015)
Background and Purpose 4-Phenylquinolin-2(1H)-one (4-PQ) derivatives can induce cancer cell apoptosis. Additional new 4-PQ analogs were investigated as more effective, less toxic antitumour agents. Experimental Approach Forty-five 6,7,8-substituted 4-substituted benzyloxyquinolin-2(1H)-one derivatives were synthesized. Antiproliferative activities were evaluated using a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazoliun bromide assay and structure-activity relationship correlations were established. Compounds 9b, 9c, 9e and 11e were also evaluated against the National Cancer Institute-60 human cancer cell line panel. Hoechst 33258 and Annexin V-FITC/PI staining assays were used to detect apoptosis, while inhibition of microtubule polymerization was assayed by fluorescence microscopy. Effects on the cell cycle were assessed by flow cytometry and on apoptosis-related proteins (active caspase-3, -8 and -9, procaspase-3, -8, -9, PARP, Bid, Bcl-xL and Bcl-2) by Western blotting. Key Results Nine 6,7,8-substituted 4-substituted benzyloxyquinolin-2(1H)-one derivatives (7e, 8e, 9b, 9c, 9e, 10c, 10e, 11c and 11e) displayed high potency against HL-60, Hep3B, H460, and COLO 205 cancer cells (IC50 50 > 50 μM). Particularly, compound 11e exhibited nanomolar potency against COLO 205 cancer cells. Mechanistic studies indicated that compound 11e disrupted microtubule assembly and induced G2/M arrest, polyploidy and apoptosis via the intrinsic and extrinsic signalling pathways. Activation of JNK could play a role in TRAIL-induced COLO 205 apoptosis. Conclusion and Implications New quinolone derivatives were identified as potential pro-apoptotic agents. Compound 11e could be a promising lead compound for future antitumour agent development.
One-step Synthesis of 3-Unsubstituted 4-Hydroxy-2(1H)-Quinoline
Menglin, Ma,Qingrong, Sun,Weiqing, Yang,Xingyi, Wang,Yinan, Xu
, p. 435 - 441 (2021/11/22)
3-Unsubstituted 4-hydroxy-2(1H)-quinolone (DHQ) derivatives were synthesized from aniline derivatives and diethyl malonate at low temperature using AlCl3 as catalyst and Eaton reagent as acidic environment. A reaction mechanism was proposed and elucidated. Different synthetic intermediates are specially prepared or purified and used to understand the reaction and validation mechanism.
Mild, efficient, and solvent-free synthesis of 4-hydroxy-2-quinolinones
Amagata, Taro,Assad, Meerna Y.,Atalay, Sanberk S.,Wu, Weiming
, (2020/03/05)
Malonic acid monoanilides were obtained in excellent yield from the reaction of anilines with Meldrum's acid under solvent-free conditions. The malonic acid monoanilide intermediates were then treated with methanesulfonic acid anhydride (MSAA) to produce 4-hydroxy-2-quinolinones in excellent yield. It should be noted that both reactions had to be run under mild conditions to avoid the decarboxylation of the malonic acid monoanilide intermediate.
