1677-36-7Relevant academic research and scientific papers
Method for preparing 4-hydroxyquinolin-2(1H)-one compound
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Paragraph 0073-0075, (2021/09/22)
The invention discloses a method for preparing a 4-hydroxyquinolin-2(1H)-one compound, which comprises the following steps of: reacting 2-ethynylaniline as shown in a formula (1) and carbon dioxide which are used as raw materials in an ionic liquid in the presence of a silver salt catalyst to obtain the 4-hydroxyquinoline-2 (1H)-one compound as shown in a formula (II). The reaction equation is shown in the specification. When the method disclosed by the invention is applied to the reaction for preparing the 4-hydroxyquinolin-2(1H)-one compound, the reaction conditions are relatively mild, the dosage of the silver salt catalyst is small, the separation and purification process of the product is relatively simple, the product yield is high, and the application range of a substrate is wide.
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.
Identification and molecular modeling of new quinolin-2-one thiosemicarbazide scaffold with antimicrobial urease inhibitory activity
Elbastawesy, Mohammed A. I.,El-Shaier, Yaseen A. M. M.,Ramadan, Mohamed,Brown, Alan B.,Aly, Ashraf A.,Abuo-Rahma, Gamal El-Din A.
, p. 13 - 27 (2020/01/22)
Abstract: A new series of 6-substituted quinolin-2-one thiosemicarbazides 6a–j has been synthesized. The structure of the target compounds was proved by different spectroscopic and elemental analyses. All the designed final compounds were evaluated for their in vitro activity against the urease-producing R. mucilaginosa and Proteus mirabilis bacteria as fungal and bacterial pathogens, respectively. Moreover, all compounds were in vitro tested as potential urease inhibitors using the cup-plate diffusion method. Compounds 6a and 6b were the most active with (IC50 = 0.58 ± 0.15 and 0.43 ± 0.09?μM), respectively, in comparison with lead compound I (IC50 = 1.13 ± 0.00?μM). Also, the designed compounds were docked into urease proteins (ID: 3LA4 and ID: 4UBP) using Open Eye software to understand correctly about ligand–receptor interactions. The docking results revealed that the designed compounds can interact with the active site of the enzyme through multiple strong hydrogen bonds. Moreover, rapid overlay of chemical structures’ analysis was described to understand the 3D QSAR of synthesized compounds as urease inhibitors. The results emphasize the importance of polar thiosemicarbazide directly linked to 6-substituted quinolone moieties as promising antimicrobial urease inhibitors. Graphic abstract: [Figure not available: see fulltext.]
New Quinoline-2-one/thiazolium bromide Derivatives; Synthesis, Characterization and Mechanism of Formation
Mostafa, Sara M.,Aly, Ashraf A.,Sayed, Samia M.,Raslan, Mohamed A.,Ahmed, Amira E.,Nafady, Ayman,Ishak, Esam A.,Shawky, Ahmed M.,Abdelhafez, El-Shimaa M.N.
, (2021/05/10)
We report on the formation of new quinoline-2-one derived by thiazolium bromides from the reaction of 3-thiosemicarbazides derived by 2-quinolones with 2-bromoacetophenones. The structure of products was elucidated by mass, IR and NMR spectra together with elemental analysis. The mechanism of products formation was discussed.
Synthesis and colon anticancer activity of some novel thiazole/-2-quinolone derivatives
Aly, Ashraf A.,Mohamed, Asmaa H.,Ramadan, Mohamed
, (2020/02/13)
We direct for the synthesis of 1,6,7-trisubstituted-4-phenylthiazol-2(3H)-ylidene)hydrazono)methyl)quinolin-2-one derivatives by the reaction of corresponding thiosemicarbazone derived by 2-quinolone derivatives with 2-bromoacetophenones in presence of triethylamine at room temperature. The mechanism of the formed products was discussed. The structure of the obtained products was fully characterized using different spectral techniques including infrared (IR), nuclear magnetic resonance (NMR), and mass spectrometry (MS) together with elemental analyses. The new synthesized compounds showed a moderate colon anticancer activity.
Arylidenes of Quinolin-2-one scaffold as Erlotinib analogues with activities against leukemia through inhibition of EGFR TK/ STAT-3 pathways
Abuo-Rahma, Gamal El-Din A.,Aly, Ashraf A.,El-Shaier, Yaseen A. M. M.,Elbastawesy, Mohammed A. I.,Ramadan, Mohamed
, (2020/02/15)
A new series of 6-substiuted-4-(2-(4-substituted-benzylidene)hydrazinyl)quinolin-2(1H)-one derivatives have been designed and synthesized. The structure of the synthesized compounds was proved by 1H NMR, 13C NMR, 2D NMR, mass and elemental analyses. The target compounds were evaluated for their in vitro cytotoxic activity against 60 cancer cell lines according to NCI protocol. Consequently, the most active compounds were further examined against the most sensitive leukemia RPMI-8226 and on healthy cell lines. 6-Chloro-derivative was the most active one; with IC50 = 15.72 ± 1.21 and 46.05 ± 2.36 μM against RPMI-8226 and normal cell lines, respectively. Also, it showed a remarkable inhibitory activity compared to gefitinib on the EGFR TK mutant, wild and on H-RAS in addition to STAT-3 with IC50 = 695.49 ± 21.8, 263.15 ± 15.13, 10.61 ± 0.27 and 1.753 ± 0.81 nM, respectively. Cell cycle analysis of RPMI-8226 cells treated with the 6-chloro-derivative showed cell cycle arrest at G2/M phase (supported by Caspases-3,8, BAX and Bcl-2 studies) with a significant pro-apoptotic activity as indicated by annexin V-FITC staining. Moreover, the docking studies ROCS analysis and Tanimoto scores supported the results. The study illustrated the effect of several factors on compounds activity.
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.
Novel Pyrazoloquinolin-2-ones: Design, synthesis, docking studies, and biological evaluation as antiproliferative EGFR-TK inhibitors
Elbastawesy, Mohammed A.I.,Aly, Ashraf A.,Ramadan, Mohamed,Elshaier, Yaseen A.M.M.,Youssif, Bahaa G.M.,Brown, Alan B.,El-Din A Abuo-Rahma, Gamal
, (2019/06/19)
Two new series of diethyl 2-[2-(substituted-2-oxo-1,2-dihydroquinolin-4-yl)hydrazono]-succinates 6a-g and 1-(2-oxo-1,2-dihydroquinolin-4-yl)-1H-pyrazoles 7a-f have been designed and synthesized. The structures of the synthesized compounds were proved by IR, mass, NMR (2D) spectra and elemental analyses. The target compounds were evaluated for their in vitro cytotoxic activity against 60 cancer cell lines according to NCI protocol. Consequently, seven compounds were further examined against the most sensitive cell lines, leukemia CCRF-CEM, and MOLT-4. 5-Amino-1-(6-bromo-2-oxo-1,2-dihydroquinolin-4-yl)-1H-pyrazole-3,4-dicarbonitrile (7f) was the most active product, with IC50 = 1.35 uM and 2.42 uM against MOLT-4 and CCRF-CEM, respectively. Also, it showed a remarkable inhibitory activity compared to erlotinib on the EGFR TK with IC50 = 247.14 nM and 208.42 nM, respectively. Cell cycle analysis of MOLT-4 cells treated with 7f showed cell cycle arrest at G2/M phase (supported by Caspases, BAX and Bcl-2 studies) with a significant pro-apoptotic activity as indicated by annexin V-FITC staining. Moreover, the docking study indicated that both the pyrazole moiety and the quinolin-2-one ring showed good fitting into EGFR (PDB code: 1M17). In order to interpret SAR of the designed compounds, and provide a basis for further optimization, molecular docking of the synthesized compounds to known EGFR inhibitors was performed. The study illustrated the effect of several factors on the compounds’ activity.
Use of nanocrystalline ZnO as an efficient and reusable catalyst for a onepot, three-component synthesis of 6-Chloro-And 5,7-Dichloro-4-Hydroxy-3-[aryl (piperidin-1-yl)methyl]quinolin-2(1H)-ones in water
Astaneh, H. R. Haghjoo,Rufchahi, E. O. Moradi
, p. 116 - 120 (2018/03/21)
A one-pot, green, efficient and facile procedure was applied for the preparation of a series of 4-hydroxy-3-[aryl(piperidin-1-yl)methyl] quinolin-2(1H)-ones via the reaction of 6-chloro-4-hydroxyquinoline-2(1H)-one 1 and/or 5,7-dichloro-4-hydroxyquinoline-2(1H)-one 2, piperidine and aromatic aldehydes in water in the presence of nanocrystalline ZnO under reflux conditions. The desired products were obtained in satisfactory yields. The nanocrystalline ZnO can be separated and reused at least up to three times with almost the same catalytic activity.
Compounds having anticonvulsion activity, preparing methods thereof and applications of the compounds
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Paragraph 0082; 0083; 0084; 0085; 0087; 0088, (2017/10/05)
The invention provides 7-substituted-5-methyl-1,2,4-triazolo[4,3-a] quinoline and 7-substituted-5-ethoxy-[1,2,4]-triazolo[4,3-a] quinoline compounds having anticonvulsion activity, preparing methods thereof and applications of the compounds in the field of preparing anticonvulsion medicines.
