ORGANIC & BIOMOLECULAR CHEMISTRY
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2014
·Vol. 13
·期 2
·601-611
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IF 3.487
Xiong-Li Liu,Bo-Wen Pan,Wen-Hui Zhang,Chao Yang,Jun Yang,Yang Shi,Ting-Ting Feng,Ying Zhou,Wei-Cheng Yuan
A highly efficient and environmentally benign method for the synthesis of oxindoles featuring two contiguous quaternary carbon centers via an aldol reaction starting from various 3-substituted oxindoles has been established. A wide variety of such featured multi-substituted 1,3-indandione ring-fused 3-oxindole scaffolds were obtained smoothly in good yields (up to 98%) employing the most green of solvents, namely water, as reaction medium. Furthermore, their biological activity has been preliminarily demonstrated by in vitro evaluation against human prostate cancer cells PC-3, human lung cancer cells A549 and human leukemia cells K562 by MTT-based assays, using the commercially available standard drug, cisplatin, as a positive control. Gratifyingly, compounds 3s, 3u, 3y and 3c′ exhibited the best levels of in vitro inhibitory activity against human leukemia cells K562, which were almost 2.0, 2.8, 2.5 and 2.2 times, respectively, the activity of the positive control, cisplatin. Compound 3y had 2.7 times the activity of the positive control, cisplatin, against PC-3 cancer cells, and 3s, 3u and 3c′ showed levels of in vitro inhibitory activity against PC-3 cancer cells that were comparable to that of cisplatin. Compounds 3s, 3u and 3y had good inhibitory ability against human lung cancer cells A549. The results indicated that 1,3-indandione ring-fused 3-oxindole analogs may be useful leads for further biological screenings.
研究领域:
有机化学
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药物化学
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肿瘤学
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产品关联
DOI
PubMed
高影响因子
CHINESE JOURNAL OF CHEMICAL ENGINEERING
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2020
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IF 2.627
Qiu Zhao,Gang Wang,Fuxia Liao,Yifan Sha,Fei Xu,Chunshan Li,Zengxi Li,Yijun Cao
An ionic liquid (IL) catalyzed solvent-free process was developed for the direct synthesis of chalcone and its derivatives by using substituted acetophenones and benzaldehydes via aldol reaction under mild conditions. A series of acidic and basic ILs were selected and screened. The influences of cations and reaction conditions on product yield and selectivity were systematically investigated. The [Bmim]OH was identified as the optimal IL, with the highest yield and selectivity reaching up to 96.7% and 100%, respectively. A reaction mechanism-based kinetic model was established and regressed with experimental data, revealing the β -Hydroxylketone dehydrolysis with activation barrier of 37.8 kJ·mol −1 was observed as the rate-controlling step.
研究领域:
有机化学
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催化化学
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产品关联
DOI
高影响因子
Molecular Catalysis
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2017
·
IF 0
An-xun Zheng,Cheng-bin Gong,Wei-jing Zhang,Qian Tang,Hai-rong Huang,Cheuk-fai Chow,Qian Tang
A series of amphiphilic molecularly imprinted polymers (MIP1, MIP2, MIP3, MIP4, MIP5, and MIP6) containing hydrophobic photoresponsive sites and hydrophilic catalytically active sites were fabricated using bifunctional monomers. These polymers were characterized by scanning electron microscopy, N 2 adsorption–desorption analysis, Fourier Transform infrared spectroscopy, thermal gravimetric analysis, and ultraviolet–visible spectroscopy. The catalytic activity of the amphiphilic molecularly imprinted polymer was investigated towards the aldol reaction between p -nitroaldehyde and acetone (a molecular enlargement reaction) in a mixed solvent of DMSO and water at room temperature. The polymer catalyst MIP3 performs best, and displayed good conversions with low catalyst loading (5 mol% of l -hydroxyproline with respect to the aldehyde) and photoswitching properties (photo-regulated conversion difference of 20%). Compared with the corresponding non-imprinted polymer, a higher binding capacity, higher conversion, and better photoswitching properties were obtained when the molecularly imprinted polymer was used as the catalyst, illustrating the importance of the specific cavities in the molecularly imprinted polymer.
研究领域:
有机化学
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材料科学
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DOI
ACS Sustainable Chemistry & Engineering
·
2025
·
IF 7.3
Jiahe Huang,Chunhong Zhang,Jianwei Bai,Yudan Wang,Toshifumi Satoh,Feng-Huei Lin
Supramolecular hydrogels have broad application prospects in asymmetric catalysis due to their unique properties, and the water environment inside the hydrogels plays an important role in green catalysis. This paper reports a novel C2-symmetric proline derivative gelator (p-L-Phe-Pro-COOH) with a hydrophobic benzene ring in the center and hydrophilic groups on both sides. The C2-symmetric structure can provide the gelator with more catalytically active sites. p-L-Phe-Pro-COOH can self-assemble in H2O or H2O/dimethyl sulfoxide (DMSO) mixed solvents to form gels with a three-dimensional network of left-handed intertwined helical nanofibers, namely, L-Hyd and L-Hyd-DMSO. The L-Hyd and L-Hyd-DMSO gels are used as catalysts for the aldol and Mannich reactions, achieving high yields (>90%), diastereoselectivity (dr >90/10 (anti/syn)), and enantioselectivity (ee value of 99%) of the products without requiring additional additives. Results indicated that the L-Hyd and L-Hyd-DMSO gels exhibited higher catalytic activity compared to that of the gelator. Further, the Mannich reaction catalyzed by L-Hyd-DMSO revealed that introducing DMSO considerably enhanced the reaction yield while maintaining a high enantioselectivity. The L-Hyd-DMSO effectively addresses the issue of low yield in Mannich reactions conducted in aqueous systems. In addition, the L-Hyd and L-Hyd-DMSO gels acting as catalysts can be recovered by simple extraction and maintain good reactivity after five cycles. The findings of this study indicate that supramolecular hydrogels show potential in asymmetric catalytic reactions, which closely align with the principles of green chemistry.
研究领域:
有机化学
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绿色化学
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材料科学
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产品关联
DOI
高影响因子
APPLIED CATALYSIS A-GENERAL
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2012
·
IF 3.903
Bo Liu,Heng Liu,Chunhua Wang,Lulu Liu,Shujie Wu,Jingqi Guan,Qiubin Kan
Bifunctionalized material with organized pairs of carboxylic acid and primary amine structurally similar to β 3 -amino acid derivatives has been prepared through post-grafted approach. Then the organized acid–base bifunctionalized material and the base monofunctionalized material were used as catalysts in aldol reaction to study the influence of the acid–base geometry on acid–base cooperativity. The catalytic result using acid–base bifunctionalized material towards aldol reaction was almost as same as the result obtained with the monofunctional amino catalyst, indicating that cooperative activation is not able to act efficiently unless the acid and the base active centers are positioned with appropriate geometry for the aldol reaction (e.g. about 2.6 Å).
研究领域:
有机化学
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催化化学
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材料化学
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分子设计
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表面功能化
✓ 已验证
DOI
高影响因子
危险品化学品经营许可证（带存储）