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SYNTHESIS-STUTTGART · 2020 ·Vol. 53 ·期 07 ·1341-1348 · IF 2.675

Photoinduced [3+2] Annulation of Alkene with o-Iodoanilines: An Expedient Approach to Indolines

Xinxin Zhao,Lin Guo,Chao Yang,Wujiong Xia

A highly regioselective [3+2] cyclization of alkenes with 2-iodoanilines under the irradiation of UV light is described. This general, metal-free strategy facilitates the direct preparation of 2-mono-/disubstituted indolines as well as spiroindolines through alkene carboamination in one step. Mechanistic studies suggested that the photochemical protocol proceeded via a radical pathway.

研究领域: 有机化学 · 合成化学
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Green Chemistry Letters and Reviews · 2019 · IF 2.754

Efficient one-pot catalyst-free synthesis of novel coumarin- spiro[indoline-3,4'-pyran] conjugates via three-component domino reaction in aqueous medium

Adil Omar,Keyume Ablajan

A simple, efficient, eco-friendly and catalyst-free procedure was developed for the construction of novel coumarin-spiro[indoline-3,4'-pyran] conjugates via three-component reactions of various synthetic beta-ketoesters with isatins and malononitrile in aqueous medium. In addition to operational simplicity and absence of tedious separation procedures, being catalyst–free is the prominent advantage of this method.

研究领域: 有机化学 · 药物化学
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NATURAL PRODUCT RESEARCH · 2020 · IF 2.158

Two new chemical constituents from the rhizomes of Actaea dahurica

Sen-Ju Ma,Hai-Bo Li,Jun-Ran Shao,Qian-Qian Pang,Ting Li,Xin-Sheng Yao,Yang Yu

A new phenylpropanoid allopyranoside (1) and a new indolinone alkaloid (2) were isolated from the rhizomes of Actaea dahurica (syn. Cimicifuga dahurica). The structures of those two compounds were deduced as cimicifugaside F (1) and 3E,11E-(3-methyl-2-butenylidene acid)-2-indolinone-1-O-β-d-glucopyranoside (2) by detailed analysis of their MS, 1D and 2D NMR data and comparison with literatures. Additionally, the isolates were evaluated for their inhibitory effects on the production of NO by LPS-stimulated RAW 264.7 macrophages.

CAS / MDL: 298-93-1
研究领域: 植物化学 · 药理学
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POLYMER · 2022 · IF 4.432

The curing reaction of phthalonitrile promoted by sulfhydryl groups with high curing activity

Yu Pu,Huanxin Xie,Xian He,Jiangbo Lv,Zhengzhu Zhu,Jinlang Hong,Ke Zeng,Jianghuai Hu,Gang Yang

The thiophenol derivative MPD was synthesized to promote the curing reaction of the phthalonitrile monomer 3BOCN to explore the promoting effect of sulfhydryl groups. Differential scanning calorimetry (DSC) and rheological measurements were performed to investigate the curing behaviors of 3BOCN/MPD blends, indicating the high curing efficiency of sulfhydryl groups. Fourier transform infrared (FTIR) and Ultraviolet–visible spectroscopy (UV–Vis) suggested that isoindoline, triazine and phthalocyanine structures were formed during the curing process. Thermal gravimetric analysis (TGA) and dynamic mechanical analysis (DMA) showed that the cured resins have excellent thermal stability and high glass transition temperature (T g ).

CAS / MDL: 123-30-8
研究领域: 材料科学 · 化学工程
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JOURNAL OF MEMBRANE SCIENCE · 2024 · IF 8.4

Robust branched Poly(p-terphenyl isatin) anion exchange membranes with enhanced microphase separation structure for fuel cells

Yijia Lei,Jialin Zhao,Jian Gao,Jingyi Wu,Na Li,Xiaoyu Chi,Yan Wang,Yiman Gu,Zhe Wang

Anion exchange membrane fuel cells (AEMFCs) are gradually becoming the focus of sustainable hydrogen energy research due to the advantages of clean by-products, faster oxidation-reduction dynamics and allowing cheap platinum-free base materials. As the key components of AEMFCs, anion exchange membranes (AEMs) are required to have high ionic conductivity and dimensional stability. This study focused on the design and preparation of branched AEMs for AEMFCs. The b-PTIN-x membranes were generated by incorporating 1,3,5-triphenylbenzene (TPB) units into rigid poly(p-terphenyl isatin) (PTI) polymer backbones. This innovative approach aimed to induce microphase separation structures by exploiting TPB with high FFV, as well as to enhance the tensile strength of AEMs with the help of branched structures. SAXS and AFM images revealed that the AEMs achieved enhanced microphase separation structures, resulting in the formation of ion transport channels with dimensions in the range of a few nanometers (3.36–3.70 nm). The branched b-PTIN-11 membranes displayed significant OH − conductivity (153.9 mS cm −1 at 80 °C) while having a low ion exchange capacity (IEC) (1.73 mmol g −1 ). The b-PTIN-11 membranes displayed improved tensile strength (56.69 MPa) and exceptional dimensional stability, with swelling ratio (SR) of 18.5 % at 80 °C. They also showed great chemical stability with 89.64 % conductivity remaining, lasting for more than 1200 h in 3 M NaOH solution at 80 °C. Ultimately, the b-PTIN-11 membrane underwent testing to evaluate its performance in a fuel cell using H 2 –O 2 . It demonstrated a peak power density (PPD) of 566 mW cm −2 when subjected to a current density of 1339 mA cm −2 .

研究领域: 材料科学 · 能源研究
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BIOORGANIC CHEMISTRY · 2022 · IF 5.307

Semi-rational protein engineering of a novel esterase from Bacillus aryabhattai (BaCE) for resolution of (R,S)-ethyl indoline-2-carboxylate to prepare (S)-indoline-2-carboxylic acid

Hongjun Zhang,Zeguang Cheng,Litian Wei,Xinjun Yu,Zhao Wang,Yinjun Zhang

A gene encoding an esterase from Bacillus aryabhattai (BaCE) was identified, synthesized and efficiently expressed in the Escherichia coli system. A semi-rational protein engineering was applied to further improve the enzyme’s enantioselectivity. Under the guidance of the molecular docking result, a single mutant BaCE-L86Q and a double mutant BaCE-L86Q/G284E were obtained, with its E max value 6.4 times and 13.9 times of the wild-type BaCE, respectively. The recombinant BaCEs were purified and characterized. The overwhelming E value demonstrated that BaCE-L86Q/G284E was a promising biocatalyst for the biological resolution to prepare ( S )-indoline-2-carboxylic acid.

研究领域: 生物技术 · 酶学 · 蛋白质工程
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APPLIED ORGANOMETALLIC CHEMISTRY · 2013 ·Vol. 27 ·期 3 ·148-154 · IF 2.011

Nano n-propylsulfonated γ-Al2O3: a new, efficient and reusable catalyst for synthesis of spiro[indoline-3,4-pyrazolo[3,4-e][1,4]thiazepine]diones in aqueous media

Li Qiang Wu

Nano n -propylsulfonated γ-Al 2 O 3 is easily prepared by the reaction of nano γ-Al 2 O 3 with 1,3-propanesultone. This reagent can be used as an efficient catalyst for the synthesis of spiro [indoline-3,4-pyrazolo[3,4- e ][1,4]thiazepine]diones in aqueous media. This new method consistently has the advantages of excellent yields and short reaction times. Further, the catalyst can be reused and recovered several times. Copyright © 2013 John Wiley & Sons, Ltd.

研究领域: 催化化学 · 有机合成 · 绿色化学 · 纳米材料 · 药物化学
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CHINESE CHEMICAL LETTERS · 2014 · IF 1.178

Selective hydrogenation of unprotected indole to indoline over N-doped carbon supported palladium catalyst

Dong-Shun Deng,Guo-Qiang Han,Xiao Zhu,Xuan Xu,Yu-Tong Gong,Yong Wang

Mesoporous N-doped carbon supported palladium catalyst Pd@CN 0.132 was able to efficiently catalyze unprotected indole to indoline under mild conditions. In the aqueous system, a selectivity of 100% and conversion of 96% was achieved under 313   K and atmospheric hydrogen gas.

研究领域: 催化 · 有机化学 · 材料科学
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iScience · 2022 ·Vol. 25 ·期 12 ·105669-105669 · IF 6.107

Copper-catalyzed oxidative dehydrogenative dearomatization of indole derivatives: A new strategy to construct spirocyclic indolenines.

Junli Chao,Yuanyuan Yue,Ke Wang,Xiaohui Guo,Chunying Sun,Yue Xu,Jianming Liu

A concise copper-catalyzed oxidative dehydrogenative dearomatization of indole derivatives for the direct synthesis of spirocyclic indolenines containing fluorene and indeno[2,1- b ]indole groups has been established. The utility of this method has also been successfully accomplished by dual oxidative dehydrogenative dearomatization to deliver the desired spirocyclic indolenines containing fluorene groups. According to mechanistic analyses, the C-H cleavage of the phenyl ring was not implicated in the rate-limiting phase. This transformation underwent a single-electron-transfer oxidation by copper(II) catalyst to afford a radical-cation intermediate, yielding the final product by nucleophilic attack and dual deprotonation.

研究领域: 有机化学 · 合成化学
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JOURNAL OF MEDICINAL CHEMISTRY · 2019 · IF 6.054

Multistage Screening Reveals 3-Substituted Indolin-2-one Derivatives as Novel and Isoform-Selective c-Jun N-terminal Kinase 3 (JNK3) Inhibitors: Implications to Drug Discovery for Potential Treatment of Neurodegenerative Diseases

Xiaodong Dou,Huixia Huang,Yibo Li,Lan Jiang,Yanxing Wang,Hongwei Jin,Ning Jiao,Lihe Zhang,Liangren Zhang,Zhenming Liu

Alzheimer’s disease (AD) is one of the most challenging diseases around the world with no effective clinical treatment. Previous studies have suggested c-Jun N-terminal kinase 3 (JNK3) as an attractive therapeutic target for AD. Herein, we report 3-substituted indolin-2-one derivatives as the first isoform-selective JNK3 inhibitors by multistage screening. In this study, comparative structure-based virtual screening was performed, and J30-8 was identified with a half-maximal inhibitory concentration of 40 nM, which exhibited over 2500-fold isoform selectivity and marked kinome-wide selectivity. Further study indicated that 1 μM J30-8 exhibited neuroprotective activity in vitro so as to alleviate the spatial memory impairment in vivo through reducing plaque burden and inhibiting the phosphorylation of JNKs, Aβ precursor protein, and Tau protein. All of these indicated J30-8 as proved isoform-selective JNK3 inhibitors that might serve as a useful tool for further JNK3 studies with AD as well as for the development of JNK3 inhibitors for the potential treatment of neurodegenerative diseases.

研究领域: 神经科学 · 药理学 · 药物发现
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