JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY
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2021
·Vol. 32
·期 6
·1270-1276
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IF 1.838
Liu Jianan,Wang Yanan,Gong Shuwen,Duan Wenzeng,Huang Xianqiang
A highly efficient and reusable catalyst QA-HPMV was successfully prepared by the reaction of quinoline-2-formic acid (QA) with molybdovanadophosphoric heteropolyacid (H4PMo11VO40, HPMV) for the nitration of benzene. The physical and chemical properties of the sample was characterized by X-ray diffraction analysis (XRD), Fourier transform infrared spectroscopy (FTIR), UV-Vis and thermogravimetric analysis (TG). The characterization results showed that the formed QA-HPMV retained the Keggin structure of HPMV. As a catalyst for benzene nitration, QA-HPMV showed good catalytic performance and the yield of nitrobenzene was 82.5% under the optimized reaction conditions. As a heterogeneous catalyst, QA-HPMV can be easily recycled from the reaction medium by filtering and remained highly catalytic performance even after five runs of recycling.
研究领域:
化学工程
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催化化学
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产品关联
DOI
高影响因子
Analytical Methods
·
2021
·Vol. 13
·期 43
·5231-5239
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IF 2.896
Xuejia Chen,Tingkai Xiong,Jin Xu,Yan Li,Min Zhang,Ying Liang
In this paper, a novel and stable fluorescent reagent, quinoline-2,3-dicarbaldehyde (QDA), is synthesized as a probe to detect ammonium in natural water. Ammonium reacts with QDA in the presence of SO32− and Ca2+ to form a fluorescence product, which has maximum excitation and emission wavelengths at 429 nm and 518 nm. The concentration of reagents, the reaction temperature, the reaction time, and the pH in the final solution are investigated and optimized. The interferences of typical organic nitrogen and inorganic compounds are evaluated, and results prove that most volatile amines have little or negligible effect. Under the optimized conditions, this method provides a limit of detection of 0.065 μmol L−1, a calibration range of 0.216–9 μmol L−1, and reproducibility (with a relative standard deviation) of 1.9% for 1.5 μmol L−1 ammonium. For water sample analysis, the proposed method provides comparable results to those of the conventional o-phthalaldehyde method but has longer reagent stability (42 days).
研究领域:
分析化学
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环境科学
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产品关联
DOI
PubMed
高影响因子
LETTERS IN ORGANIC CHEMISTRY
·
2024
·Vol. 22
·期 1
·56-60
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IF 0.7
Xin-Yu Lin,Guo-Jun Chen,Su-Zhe Wu,Ke-Xuan Xu,Xiao-Tian Zhang,Qi Feng
4-Hydroxyquinoline-2(1H)-ones exhibit multiple biological activities, and studying their synthetic methods is of great significance. In the presence of tetramethylguanidine and silver nitrate, 4-hydroxyquinoline-2(1H)-ones were efficiently synthesized from 2-ethynylanilines and carbon dioxide under atmospheric pressure. The reaction conditions, such as types of silver catalysts and reaction solvents, were optimized, and the applicability of the substrate was preliminarily investigated. This method provides an alternative pathway for the synthesis of 4-hydroxyquinoline-2(1H)-ones and the conversion and utilization of carbon dioxide.
研究领域:
有机化学
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药物化学
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DOI
高影响因子
BIOORGANIC CHEMISTRY
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2020
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IF 4.831
Shiben Wang,Hui Liu,Kang Lei,Guangyong Li,Jun Li,Yuyu Wei,Xuekun Wang,Renmin Liu
In this study, a series of 3,4-dihydroquinolin-2(1 H )-one derivatives were designed and synthesized using two experimental models, namely maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ), to test the anticonvulsant activity of the target compound in vivo (i.p. in Kunming mice). The neurotoxicity (NT) of the target compound was measured by the rotating rod method (i.p. in Kunming mice). Six compounds with potential activity were selected from the two experimental models to test the 50% effective dose (ED 50 ). In vitro binding experiments with the GABA A receptor were also performed. The results of the pharmacological experiments showed that compound 7-((5-(pentylthio)-1,3,4-oxadiazol-2-yl)methoxy)-3,4-dihydroquinolin-2(1 H )-one ( 5b ) showed the best anticonvulsant activity (MES, ED 50 = 10.1 mg/kg; scPTZ, ED 50 = 9.3 mg/kg), which was superior to activities shown by carbamazepine and ethosuximide, and it also exhibited the most potent binding affinity to GABA A receptors (IC 50 = 0.12 μM). The GABA content in Wistar rat brains (i.p.) was also investigated, and the results showed that compound 5b may have a certain effect on the GABA system, as it increased the GABA concentration in the brain of rats. Molecular docking was used to study the binding mode of compound 5b and the GABA A receptor. Compound 5b showed significant interactions with residues at the benzodiazepines binding site on the GABA A receptor. The physicochemical and pharmacokinetic properties of the target compounds were predicted using Discovery Studio 2019 and ChemBioDraw Ultra 14.0.
研究领域:
药理学
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神经科学
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药物化学
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DOI
PubMed
高影响因子
ORGANIC & BIOMOLECULAR CHEMISTRY
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2022
·Vol. 20
·期 15
·3201-3210
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IF 3.89
Lin Chen,Wei Liang
Michael/ammonolysis cascade reactions between cyclohexane-1,3-dione-derived enaminones and olefinic azlactones via phase-transfer catalysis have been developed. This method provides rapid access to a suite of architecturally complex and diverse quinoline-2,5-diones bearing a secondary amide group at the C-3 position in moderate to excellent yields (53–94%) and with excellent diastereoselectivities (>99 : 1 dr in most cases). The achievement of a preparative-scale reaction and the diverse product derivatization that can be obtained highlight the application potential of this protocol both in academic and industrial settings. An investigation of the reaction mechanism implies that tetrabutylammonium hydroxide may be the actual catalyst during this cascade reaction.
研究领域:
有机化学
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药物化学
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DOI
高影响因子
JOURNAL OF MEDICINAL CHEMISTRY
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2023
·
IF 7.3
Bei Zhang,Yi-Yi Yang,Zheng-Jiong Zhao,Run-Duo Liu,Ling-Ling Feng,Mei-Yan Jiang,Yijun Yuan,Shuheng Huang,Zhe Li,Quan Wang,Hai-Bin Luo,Yinuo Wu
Phosphodiesterase 1 (PDE1) is a subfamily of PDE super enzyme families that can hydrolyze cyclic adenosine monophosphate and cyclic guanosine monophosphate simultaneously. Currently, the number of PDE1 inhibitors is relatively few, significantly limiting their application. Herein, a novel series of quinolin-2(1H)-ones were designed rationally, leading to compound 10c with an IC50 of 15 nM against PDE1C, high selectivity across other PDEs, and remarkable safety properties. Furthermore, we used the lead compound 10c as a chemical tool to explore whether PDE1 could work as a novel potential target for the treatment of inflammatory bowel disease (IBD), a disease which is a chronic, relapsing disorder of the gastrointestinal tract inflammation lacking effective treatment. Our results showed that administration of 10c exerted significant anti-IBD effects in the dextran sodium sulfate-induced mice model and alleviated the inflammatory response, indicating that PDE1 could work as a potent target for IBD.
研究领域:
药理学
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药物化学
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炎症性疾病
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DOI
PubMed
高影响因子
BIOORGANIC CHEMISTRY
·
2024
·
IF 4.5
Qian Zhou,Wei-Hao Luo,Bei Zhang,Zhao-Hang Xue,Qing-Hua Huang,Ling-Ling Feng,Yinuo Wu,Chen Zhang
Inflammatory bowel disease (IBD) is a chronic inflammatory disease that affects the entire gastrointestinal tract. The complex etiology of IBD made it difficult to cure. Phosphodiesterases (PDEs) have garnered significant attention due to their involvement in immune and inflammatory responses in IBD. Most recently, we have reported a novel PDE1 inhibitor 1 with quinolin-2(1 H )-one scaffold, demonstrating anti-IBD effects. However, its short half-life (t 1/2 ) in the rat liver microsomes (RLMs) is relatively short. In this study, structural optimization of compound 1 was performed to improve metabolic stability. Combined with molecular docking and dynamics simulations, a series of quinolin-2(1 H )-one derivatives were synthesized. Among them, compound 7a showed an excellent IC 50 value of 11 nM, high selectivity to PDE1 compared to other PDEs, and good metabolic stability with RLM t 1/2 of 67.3 min. The binding pattern between 7a and PDE1 revealed an additional hydrogen bond with Cys410, which could enhance the inhibitory activity. Furthermore, compound 7a demonstrated anti-inflammatory properties by reducing cytokine production and antioxidant activity in LPS-induced Raw264.7 cells, which contributed to its effectiveness against IBD. We believe that compound 7a could serve as an ideal tool for further pharmacological research on IBD.
研究领域:
药理学
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药物化学
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炎症研究
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DOI
高影响因子
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