- Technology of preparing 8-hydroxy-5-nitroquinoline
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An efficient, two stage method is proposed for the preparation of 8-hydroxy-5-nitroquinoline based on the nitrosation of 8-hydroxyquinoline and subsequent oxidation of the nitroso derivative using nitric acid. The conditions for the nitrosation and oxidation of the 8-hydroxyquinoline (concentration of nitric acid, temperature, and reaction time) were optimized. A method for purifying the target compound is presented.
- Isaev,Lomovskii,Korolev,Karimov
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- Synthesis and anti-phytopathogenic activity of 8-hydroxyquinoline derivatives
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Phytopathogenic fungi have become a serious threat to the quality of agricultural products, food security and human health globally, necessitating the need to discover new antifungal agents with de novo chemical scaffolds and high efficiency. A series of 8-hydroxyquinoline derivatives were designed and synthesized, and their antifungal activity was evaluated against five phytopathogenic fungi. In vitro assays revealed that most of the tested compounds remarkably impacted the five target fungi and their inhibitory activities were better than that of the positive control azoxystrobin. Compound 2, in particular, exhibited the highest potency among all the tested compounds, with an EC50 of 0.0021, 0.0016, 0.0124, 0.0059 and 0.0120 mM respectively against B. cinerea, S. sclerotiorum, F. graminearum, F. oxysporum and M. oryzae, followed by compound 5c. The morphological observations of optical microscopy and scanning electron microscopy revealed that compounds 2 and 5c caused mycelial abnormalities of S. sclerotiorum. Futhermore, the results of in vivo antifungal activity of compounds 2 and 5c against S. sclerotiorum showed that 5c possessed stronger protective and curative activity than that of 2, and the curative effects of 5c at 40 and 80 μg mL-1 (84.18% and 95.44%) were better than those of azoxystrobin (77.32% and 83.59%). Therefore, compounds 2 and 5c are expected to be novel lead structures for the development of new fungicides.
- Yin, Xiao-Dan,Sun, Yu,Lawoe, Raymond Kobla,Yang, Guan-Zhou,Liu, Ying-Qian,Shang, Xiao-Fei,Liu, Hua,Yang, Yu-Dong,Zhu, Jia-Kai,Huang, Xiao-Ling
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p. 30087 - 30099
(2019/10/04)
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- Study on Relationship Between Fluorescence Properties and Structure of Substituted 8-Hydroxyquinoline Zinc Complexes
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Organic light-emitting diodes (OLEDs) produced from 8-hydroxyquinoline metal complexes play a vital role in modern electroluminescent devices. In this manuscript, a series of 8-hydroxyquinoline derivatives were synthesized by different methods and their corresponding zinc metal complexes were prepared. The UV and fluorescence properties of the complexes were measured aiming to understand the effect of substituents at the quinoline ring on the fluorescence properties of the complexes. When the C-5 of 8-hydroxyquinoline was replaced by halogen group, the fluorescence emission wavelengths had been red-shifted, at the same time, blue-shifted of fluorescence emission wavelength was observed when the C-5 position of 8-hydroxyquinoline was substituted by electron-withdrawing group. When the C-4 position of 8-hydroxyquinolie was substituted by methyl or the C-5 position was substituted by sulfonic acid group, the corresponding zinc complexes had higher fluorescence intensity than 8-hydroxyquinolie zinc.
- Jianbo, He,Tingting, Zhou,Yongjing, Cao,Yuanyuan, Zhang,Weiqing, Yang,Menglin, Ma
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p. 1121 - 1126
(2018/08/17)
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- Substituted oxines inhibit endothelial cell proliferation and angiogenesis
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Two substituted oxines, nitroxoline (5) and 5-chloroquinolin-8-yl phenylcarbamate (22), were identified as hits in a high-throughput screen aimed at finding new anti-angiogenic agents. In a previous study, we have elucidated the molecular mechanism of antiproliferative activity of nitroxoline in endothelial cells, which comprises of a dual inhibition of type 2 human methionine aminopeptidase (MetAP2) and sirtuin 1 (SIRT1). Structure-activity relationship study (SAR) of nitroxoline offered many surprises where minor modifications yielded oxine derivatives with increased potency against human umbilical vein endothelial cells (HUVEC), but with entirely different as yet unknown mechanisms. For example, 5-nitrosoquinolin-8-ol (33) inhibited HUVEC growth with sub-micromolar IC50, but did not affect MetAP2 or MetAP1, and it only showed weak inhibition against SIRT1. Other sub-micromolar inhibitors were derivatives of 5-aminoquinolin-8-ol (34) and 8-sulfonamidoquinoline (32). A sulfamate derivative of nitroxoline (48) was found to be more potent than nitroxoline with the retention of activities against MetAP2 and SIRT1. The bioactivity of the second hit, micromolar HUVEC and MetAP2 inhibitor carbamate 22 was improved further with an SAR study culminating in carbamate 24 which is a nanomolar inhibitor of HUVEC and MetAP2. The Royal Society of Chemistry 2012.
- Bhat, Shridhar,Shim, Joong Sup,Zhang, Feiran,Chong, Curtis Robert,Liu, Jun O.
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supporting information; experimental part
p. 2979 - 2992
(2012/05/07)
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- Synthesis and molecular modeling studies of 3-chloro-4-substituted-1-(8- hydroxy-quinolin-5-yl)-azetidin-2-ones as novel anti-filarial agents
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A series of 3-chloro-4-substituted-1-(8-hydroxy-quinolin-5-yl)-azetidin-2- ones were synthesized and evaluated for their in vitro anti-filarial activity. To pre-assess the anti-filarial behavior of synthesized compounds (V a-f) on a structural basis, automated docking studies were carried out with Molecular Design Suite (MDS v 3.5) into the active site of glutathione-S-transferase (GST) enzyme; scoring functions of these compounds at the active site of the GST enzyme were used for correlation with observed activity. Compounds Ve and Vf have shown good affinity for receptor GST, as well as in vitro anti-filarial potency.
- Chhajed, Santosh S.,Manisha, Puranik,Bastikar, Virupaksha A.,Animeshchandra, Haldar,Ingle,Upasani, Chandrashekhar D.,Wazalwar, Sachin S.
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experimental part
p. 3640 - 3644
(2010/09/17)
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