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Catalysts · 2023 ·Vol. 13 ·期 7 ·1060 · IF 3.9

Copper-Catalyzed N-Arylation of Pyranoquinolinones with Boronic Acids at Room Temperature without Ligand

Wei Gao,Fang Gao,Haikuan Yang,Zongde Wang,Yaru Huang

Pyranoquinolinones synthesized from citral were used for Cu-catalyzedN-arylation with a wide range of arylboric acids. The reaction proceeded well with a broad substrate scope, providing a direct way to access highly functional pyranoquinolinone core structure derivatives in yields of up to 80%. Compared to citral, the compounds we obtained have a much better inhibitory effect on HeLa cervical cancer cells, and compound3phas an IC50value of 4.6 μM, lower than cisplatin’s 5.9 μM.Keywords:citral;pyranoquinolinone;N-arylation

研究领域: 有机化学 · 药物化学 · 癌症研究
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2023 · IF 4.4

Two novel fluorescent probes based on quinolinone for continuous recognition of Al3+ and ClO−

Cheng-lu Zhang,Chang Liu,Shi-ru Nie,Xiang-ling Li,Yi-ming Wang,Yang Zhang,Jing-hao Guo,Yue-dong Sun

On the basis of classical Schiff base reaction, two novel and efficient fluorescent probes ( DQNS , DQNS1 ) were designed and synthesized by introducing Schiff base structure into dis-quinolinone unit for structural modification, which can be used to detect Al 3+ and ClO − . Because the power supply capacity of H is weaker than that of methoxy, DQNS shows better optical performance: a large Stokes Shift (132 nm), identify Al 3+ and ClO − with high sensitivity and selectivity, low detection limit (29.8 nM and 25 nM) and fast response time (10 min and 10 s). Through the working curve and NMR titration experiment, the recognition mechanism of Al 3+ and ClO − (PET and ICT) probes are confirmed. Meanwhile, it is speculated that the probe has continuity for the detection of Al 3+ and ClO − . Furthermore, DQNS detection of Al 3+ and ClO − was applied to real water samples and living cell imaging.

CAS / MDL: 1318-59-8
研究领域: 化学 · 生物学
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JOURNAL OF MOLECULAR STRUCTURE · 2019 · IF 2.12

Benzimidazole-isoquinolinone functioned thiourea for selective and reversible recognition of fluoride ion

Dongmei Li,ZhongzhenTian

Two novel fluoride ion probes 11-(2-iminothiourea-2-phenyl)benzimidazole-isoquinolinone ( 3 ) and 10-(2-iminothiourea-2-phenyl)benzimidazole-isoquinolinone ( 3′ ) have been designed, synthesized and confirmed structurally by 1 H NMR、 13 C NMR and HRMS-ESI. Obvious color changes could be seen by naked-eye after the addition of F − to the DMSO solution of above probes. Both probes showed dual-channel properties: UV–vis absorption red-shift and fluorescence turn-off upon reacting with F − . More importantly, the F − induced visual and spectroscopic changes were fully reversible upon addingHSO 4 - .And the new probes could realize the distinguish recognition of F − and OH − by adding over 40 equivalents OH − . The detection limits of new probes were 0.6 nM. The recognition mechanism deduced from the 1 H NMR titration experiment and theoretical calculation was a combined process including hydrogen bonding and deprotonation between the probes and fluoride ion.

研究领域: 分析化学 · 分子生物学
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FOOD CHEMISTRY · 2025 · IF 9.8

1,3,4-Thiadiazole and quinolinone based multifunctional probes for fluorescence turn-on and colorimetric monitoring of Al3+ and Fe3+ in food and aqueous environment applications

Jinwei Tian,Yao Wei,Chengwei Lü

To achieve the development of fluorescence turn-on probe and dual detection of Al 3+ and Fe 3+ , three organic molecules (named KN , KP and KS ) were synthesized based on quinolinone, Schiff base, 1,3,4-thiadiazole or benzothiazole units. Their fluorescence characteristics and response mechanism were investigated thoroughly. The recognition process created obvious color change under sunlight and nearly 30 to 66 folds fluorescence enhancement under ultraviolet light. The formation of stable complexes leads to inhibition of intramolecular charge transfer, restriction of imine isomerization and consequent optical behaviors. For KN , Al 3+ and Fe 3+ could be distinguished via different UV–vis response or by using masking agent with detection limits of 0.18 μM and 0.20 μM, respectively. Another satisfactory result for distinguishing two ions was achieved with KS under pH = 2 or 10 condition. More importantly, KN and KS were successfully used to detect Al 3+ or Fe 3+ in foods, water samples and pharmaceutical products.

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BIOTECHNOLOGY AND APPLIED BIOCHEMISTRY · 2021 ·Vol. 69 ·期 4 ·1428-1437 · IF 2.431

Converting the 3-quinuclidinone reductase from Agrobacterium tumefaciens into the ethyl 4-chloroacetoacetate reductase by site-directed mutagenesis

Di Liu,Linbo Gou,Yajun Bai,Tai-Ping Fan,Xiaohui Zheng,Yujie Cai

In this study, the 3-quinuclidinone reductase from Agrobacterium tumefaciens (AtQR) was modified by site-directed mutagenesis. And we further obtained a saturation mutant library in which the residue 197 was mutated. A single-point mutation converted the wild enzyme that originally had no catalytic activity in reduction of ethyl 4-chloroacetoacetate (COBE) into an enzyme with catalytic activity. The results of enzyme activity assays showed that the seven variants could asymmetrically reduce COBE to ethyl ( S )-4-chloro-3-hydroxybutyrate (( S )-CHBE) with NADH as coenzyme. In the library, the variant E197N showed higher catalytic efficiency than others. The E197N was optimally active at pH 6.0 and 40°C, and the catalytic efficiency ( k cat / K m ) for COBE was 51.36 s –1 ·mM –1 . This study showed that the substrate specificity of AtQR could be changed through site-directed mutagenesis at the residue 197.

研究领域: 生物化学 · 酶学 · 生物催化
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