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ORGANOMETALLICS · 2020 · IF 3.804

Palladium-Catalyzed Cyclobutanation of Aryl Sulfonates through both C–O and C–H Cleavage

Liangwei Zhang,Long Liu,Tianzeng Huang,Qizhi Dong,Tieqiao Chen

A palladium-catalyzed cyclobutanation of aryl sulfonates with strained alkenes has been developed. The methodology is featured to achieve the cleavage of both C–O and C–H bonds of phenol derivatives in one pot. Under the reaction conditions, in addition to reactive triflates, the relatively inactive tosylates and mesylates can also be transformed into the corresponding benzocyclobutanes in high yields. This reaction can be carried out in gram-scale experiments with a low loading of the palladium catalyst and is applicable to the cyclobutanative modification of bioactive molecules, highlighting its synthetic value in organic synthesis.

研究领域: 有机化学 · 催化化学 · 合成化学
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MOLECULES · 2022 ·Vol. 27 ·期 6 ·1950 · IF 4.927

Determination of Methyl Methanesulfonate and Ethyl Methylsulfonate in New Drug for the Treatment of Fatty Liver Using Derivatization Followed by High-Performance Liquid Chromatography with Ultraviolet Detection

Yue Wang,Jing Feng,Song Wu,Huihui Shao,Wenxuan Zhang,Kun Zhang,Hanyilan Zhang,Qingyun Yang

A new derivatization high-performance liquid chromatography method with ultraviolet detection was developed and validated for the quantitative analysis of methanesulfonate genotoxic impurities in an innovative drug for the treatment of non-alcoholic fatty liver disease. In this study, sodium dibenzyldithiocarbamate was used as a derivatization reagent for the first time to enhance the sensitivity of the analysis, and NaOH aqueous solution was chosen as a pH regulator to avoid the interference of the drug matrix. Several key experimental parameters of the derivatization reaction were investigated and optimized. In addition, specificity, linearity, precision, stability, and accuracy were validated. The determined results of the samples were consistent with those obtained from the derivatization gas chromatography–mass spectrometry analysis. Thus, the proposed method is a reliable and practical protocol for the determination of trace methanesulfonate genotoxic impurities in drugs containing mesylate groups.

研究领域: 药物分析 · 毒理学 · 分析化学
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JOURNAL OF ORGANIC CHEMISTRY · 2021 · IF 4.354

Practical Electro-Oxidative Sulfonylation of Phenols with Sodium Arenesulfinates Generating Arylsulfonate Esters

Zhibin Tian,Qihang Gong,Tianzeng Huang,Long Liu,Tieqiao Chen

A practical and sustainable synthesis of arylsulfonate esters has been developed through electro-oxidation. This reaction employed the stable and readily available phenols and sodium arenesulfinates as the starting materials and took place under mild reaction conditions without additional oxidants. A wide range of arylsulfonate esters including those bearing functional groups were produced in good to excellent yields. This reaction could also be conducted at a gram scale without a decrease of reaction efficiency. Those results well demonstrated the potential synthetic value of this reaction in organic synthesis.

研究领域: 有机化学 · 绿色化学
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CATALYSIS LETTERS · 2010 ·Vol. 139 ·期 1 ·56-60 · IF 2.021

Highly Efficient Pd-Catalyzed Cyanation of Aryl Chlorides and Arenesulfonates with Potassium Ferrocyanide in Aqueous Media

Zhang Junli,Chen Xiaorong,Hu Tongjie,Zhang Yuan,Xu Kunling,Yu Yanpeng,Huang Jun

Abstract A highly improved Pd-catalyzed cyanation of aryl chlorides to corresponding benzonitriles was demonstrated in aqueous media. Moreover, Pd-catalyzed cyanation of aryl tosylates and benzenesulfonates with K 4 [Fe(CN) 6 ] was developed under the similar conditions, which extended application scope of the cyanation. Graphical Abstract

研究领域: 有机化学 · 绿色化学
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HORTSCIENCE · 2021 ·Vol. 56 ·期 8 ·909-914 · IF 1.455

Development of Bottle Gourd Lines Resistant to Zucchini Yellow Mosaic Virus Using Ethyl Methanesulfonate Mutagenesis

Asma Mohammed Saeed Al-Kubati,Baoshan Kang,Liming Liu,Aqleem Abbas,Qinsheng Gu

Zucchini yellow mosaic virus (ZYMV) causes serious damage to cucurbit crops worldwide and can be spread by aphids, by mechanical injury, and in seeds. With the popularization of cucurbit grafting, the use of susceptible rootstock has increased the risk of ZYMV infection in cucurbit crops. In China, the bottle gourd (Lagenaria siceraria) is a widely used rootstock in grafted watermelon production. However, few resistant bottle gourds are available commercially. This study developed bottle gourd lines resistant to ZYMV using ethyl methanesulfonate (EMS) mutagenesis. A new mutated bottle gourd population (M1) was generated by treating seeds with EMS. Diverse phenotypes were observed in the seedlings, flowers, and fruit of M2 plants, some of which are of potential commercial interest, such as dwarfing and different fruit shapes. Based on the M2 phenotypes, 106 M3 lines were selected and screened for resistance to ZYMV by mechanical inoculation and agroinfiltration. Nine M3 lines were resistant to ZYMV during three tests. One inbred M4 line (177-8) was developed and showed stable resistance and no virus when tested using a double-antibody sandwich enzyme-linked immunosorbent assay (DAS-ELISA) and polymerase chain reaction. These resistant lines are promising materials for developing watermelon rootstock and exploring resistance genes as new ZYMV-resistant resources. EMS induction could be a practical strategy for creating resistant cucurbit crops.

研究领域: 植物学 · 遗传学 · 作物科学
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COMBINATORIAL CHEMISTRY & HIGH THROUGHPUT SCREENING · 2022 ·Vol. 25 ·期 12 ·2026-2032 · IF 1.714

Combinatorial Synthesis of Sulfonate Derivatives of α/β-Naphthol as Anti- Oomycete Agents

Che Zhiping,Zhang Song,He Jiaxuan,Sun Di,Guo Xiaolong,Li Yuanhao,Zhu Lina,Guo Yihao,Liu Yibo,Tian Yuee,Huang Xiaobo,Liu Shengming,Chen Genqiang

Background: Developing new, efficient, and environment-friendly small molecule fungicides is the key to effectively prevent and control plant pathogenic oomycetes. α/β-Naphthol is an important raw material for drug synthesis. Due to its special structure, α/β-naphthol and its analogs possess significant biological activity. The preparation and anti-oomycete activity of novel sulfonate derivatives based on α/β-naphthol against Phytophthora capsici have not been reported yet. Methods: Thirty-two sulfonate derivatives of α/β-naphthol (4a-p and 5a-p) were prepared. The structure of all title compounds was identified by 1H NMR, MS, and m.p. The anti-oomycete activity of 4a-p and 5a-p against P. capsici was determined using the mycelial growth rate method. Results: With our ongoing research aimed at the discovery and development of fungicidal agents, 4a-p and 5a-p were designed and synthesized, and their anti-oomycete activity against P. capsici was evaluated in vitro. Two compounds 4a and 5a were found to have good anti-oomycete activity against P. capsici, and their corresponding EC50 values were 63.41 and 65.21 mg/L, respectively. Conclusion: It has been observed that the substituent R in these derivatives is aliphatic, which is very important for maintaining their anti-oomycete activity. The results lay a foundation for further design and development of sulfonate derivatives of α/β-naphthol as fungicidal agents. The structure- fungicidal activity relationship of α/β-naphthol derivatives is under investigation in our laboratory.

研究领域: 植物病理学 · 有机化学 · 农药科学
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TETRAHEDRON · 2024 · IF 2.1

Ppm-Pd-Fe nanoparticles on charcoal: Palladium catalyzed Suzuki-Miyaura cross-coupling reactions of aryl triflates with aryl neopentylglycolboronates

Zixu Li,Fei Wang,Kai Ma,Chao Fang,Qiang Jia,Changhu Chu

Aryl triflate is a type of facile and readily available compounds, which could be used as an alternative substrate for Suzuki cross coupling. In this manuscript, a novel ppm-Pd-Fe/C catalyst has been developed by reduction of palladium acetate and iron trichloride with aqueous hydrazine in situ and supported on activated charcoal. In combined with Sphos, and metal zinc as additives, this catalyst, with 300 ppm palladium loading, could be applied in the Suzuki cross coupling between aryl triflates with aryl neopentylglycolboronates.

研究领域: 有机化学 · 催化 · 材料科学
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2024 · IF 4.3

Rapidly responsive and highly selective NIR fluorescent probe for detecting hydrogen sulfide in food samples and living cells

Xuejing Xu,Yuling Zeng,Haichang Ding,Qianling Liu,Liangtao Mao,Gang Liu,Shouzhi Pu

Hydrogen sulfide (H 2 S) is a pungent gas that is one of the key mediators of signal transduction in biological systems, and its presence is related to the freshness of some protein foods. Using phenothiazine derivatives as fluorophores and 2, 4-dinitrobenzene sulfonate (DNBS) fragments as reaction groups, a near-infrared (NIR) probe WX-HS for H 2 S identification was designed. With the addition of H 2 S, WX-HS appeared a strong fluorescence signal at 660 nm with short reaction time (90 s) and high sensitivity, and fluorescence state change from non-fluorescent to orange-red. In addition, WX-HS could effectively detect H 2 S produced during food oxidation. Based on its low cytotoxicity, the WX-HS probe further enabled the detection and imaging of H 2 S in A549 cells.

研究领域: 分析化学 · 生物化学 · 食品科学 · 细胞生物学
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