BIOORGANIC CHEMISTRY
·
2025
·
IF 4.7
Lixin Niu,Yun He,Xing Zhang,Yanfei Peng,Ding Wang,Tao Wang,Zunting Zhang
A concise and efficient photo-induced rearrangement and oxidation of 2-(3-methylbenzofuran-2-yl)-3-phenyl-1 H -indoles 1 for the synthesis of 5-(2-hydroxyphenyl)-5-methyl-5,7-dihydro-6 H -benzocarbazol-6-ones 2 is described. Irradiation of compounds 1 in anhydrous dichloromethane solution, using 313 nm UV light in an air atmosphere, resulted in the formation of compounds 2 with yields ranging from 55% to 98%. Using the 6π-electrocyclization strategy of compounds 1 containing a methyl, a quaternary carbon stereocenter was introduced in the compounds 2 . The carbonyl group of compounds 2 was formed by the photo-induced oxidation of C-H bond to C-OH and hemiketal-keto tautomerization. Additionally, the antitumor activities of compounds 2 were evaluated and found to demonstrate equivalent or superior activity compared to Cisplatin against various tumor cell lines, including leukemia HL-60, lung cancer A549, liver cancer HepG2, breast cancer MDA-MB-231 and colon cancer SW480. The anticancer activity of compound 2f was particularly significant, with IC 50 values of 2.99, 9.06, 6.81, 9.29, and 14.93 μM respectively, and its IC 50 value of normal cells 11.18 μM. Compound 2k had a relatively high IC 50 values against cancer cells, whereas its IC 50 value greater than 40μM for normal cells.
研究领域:
有机化学
·
药物化学
·
肿瘤学
✓ 已验证
DOI
PubMed
高影响因子
Reaction Chemistry & Engineering
·
2020
·Vol. 5
·期 8
·1397-1404
·
IF 3.441
Xin Pan,Sihua Wu,Deshan Yao,Lian Liu,Lina Zhang,Zixuan Yao,Yan Pan,Siyuan Chang,Bingfeng Li
5-Hydroxymethyl-2-furancarboxylic acid (HMFCA) is a significant added-value intermediate derivatized from the bio-based platform chemical 5-hydroxymethylfurfuraldehyde (HMF). In the HMFCA biosynthesis process, the catalytic performance of the biocatalyst always decreases due to the presence of HMF toxicity, which is not conducive to achieving high product accumulation. Herein, we successfully obtained a new whole-cell biocatalyst from Pseudomonas aeruginosa PC-1, which was first reported to produce HMFCA from HMF. After optimization, 90.1% yield of HMFCA was attained within 6 h using a 100 mM substrate. Importantly, a much lower cell dosage was needed in the process. In order to achieve higher HMFCA accumulation, a fed-batch strategy was developed by using the growing cells from P. aeruginosa PC-1. Consequently, a total concentration of 721 mM HMFCA was obtained from 800 mM HMF within 58 h after 8 cycles of fed-batch, which is the highest concentration to date. The efficient HMFCA production made P. aeruginosa PC-1 a promising whole-cell biocatalyst for selective, large scale biotransformation of HMF.
研究领域:
生物化学
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微生物学
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工业生物技术
✓ 已验证
产品关联
DOI
高影响因子
APPLIED CLAY SCIENCE
·
2023
·
IF 5.6
Xuemin Zhong,Peng Yuan,Samahe Sadjadi,Dong Liu,Yanfu Wei
The oxidation of 5-hydroxymethylfurfural (HMF) to 2, 5-diformylfuran (DFF) is an important reaction for the conversion of renewable biomass into feedstock chemicals. In this work, palygorskite (Pal)-supported ruthenium (Ru) catalysts were developed for the efficient selective oxidation of HMF to DFF. Using natural clay mineral palygorskite as the support enabled the immobilization and dispersion of Ru nanoparticles . A 100% HMF conversion, 98% DFF yield, and 98% DFF selectivity were obtained over Ru(III)/Pal catalyst after 4.5 h under the optimal reaction conditions at 110 °C and 10 bar of O 2 in toluene. Ru nanoparticles and palygorskite synergistically achieve the excellent catalytic performance of the catalyst. The Ru metal active sites facilitate the activation of the reactants or intermediates, accelerating the formation of DFF. Furthermore, due to their different particle sizes and Ru species, the Ru(III)/Pal catalyst exhibits higher catalytic activity than the Ru(0)/Pal catalyst for the oxidation of HMF to DFF. The palygorskite-enhanced dispersion effect on Ru nanoparticles augments the catalytic activity. Moreover, the palygorskite-supported Ru catalyst showed good stability and was reused for at least five times consecutive cycles without significant loss of its catalytic activity.
研究领域:
催化
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化学工程
·
材料科学
✓ 已验证
产品关联
DOI
高影响因子
ANALYTICAL CHEMISTRY
·
2018
·
IF 6.042
Mengzhe Guo,Liyan Zhang,Yan Du,Wencheng Du,Dantong Liu,Cheng Guo,Yuanjiang Pan,Daoquan Tang
5-(Hydroxymethyl)-2′-deoxycytidine (5-hmdC), 5-(formyl)-2′-deoxycytidine (5-fodC), and 5-(carboxyl)-2′-deoxycytidine (5-cadC) are crucial intermediate products of the DNA demethylation pathway, which can also act as potential biomarkers reflecting the diagnosis and prognosis in multiple tumors. Detecting 5-hmdC, 5-fodC, and 5-cadC in human urine has various advantages including readily available samples and being noninvasive to patients. However, few works have reported the detection of 5-fodC and 5-cadC due to their trace amounts. Here we developed a novel magnetic hyper-cross-linked microporous polymer (HMP) material based on polyionic liquid (PIL) for the enrichment of 5-hmdC, 5-fodC, and 5-cadC. These magnetic PIL-HMP materials provided specific enrichment superiority for three modified cytidines. After enrichment, the signal intensity of 5-hmdC, 5-fodC, and 5-cadC increased 10–75-fold with lower limits of quantitation (LLOQ) of 0.049, 0.781, and 0.781 ng/mL, respectively. The recoveries were approximately 86.5–95.2% for 5-hmdC, 95.2–107.8% for 5-fodC, and 99.4–102.4% for 5-cadC under the relative standard deviation (RSD) of 0.2–10.3%. Finally, we successfully applied magnetic PIL-HMP materials coupled with high-performance liquid chromatography–electrospray ionization tandem mass spectrometry (HPLC-ESI-MS/MS) in enrichment and quantitative determination of 5-hmdC, 5-fodC, and 5-cadC in human urine of 10 breast cancer patients and 10 healthy people. We found that the level of 5-hmdC decreased in breast cancer patients (p < 0.05), while the levels of 5-fodC and 5-cadC increased (p < 0.05, p < 0.01). Our results demonstrated that the levels of metabolic 5-hmdC, 5-fodC, and 5-cadC in human urine are closely related to breast cancer, which could contribute to the clinical diagnosis and investigation of breast cancer and its occurrence and development mechanisms.
研究领域:
医学
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分析化学
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肿瘤学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
JOURNAL OF INDUSTRIAL AND ENGINEERING CHEMISTRY
·
2014
·
IF 2.063
Yongshen Ren,Bing Liu,Zehui Zhang,Jintao Lin
Three kinds of silver-exchanged phosphotungstic acid catalysts were prepared and used for the synthesis of potential biofuel 5-ethoxymethylfurfural (EMF). It was found that the partially silver exchanged phosphotungstic acid (Ag 1 H 2 PW) showed the best catalytic activity among silver exchanged phosphotungstic acids prepared. The highest EMF yield of 88.7% was obtained from 5-hydroxymethylfurfural (HMF) at 100 °C after 10 h. Furthermore, Ag 1 H 2 PW also showed high catalytic activity for the one-pot conversion of fructose into EMF with a yield of 69.5%. In addition, Ag 1 H 2 PW could be reused several times without a significant loss of its catalytic activity.
研究领域:
化学工程
·
可再生资源化学
✓ 已验证
DOI
高影响因子
Biomass Conversion and Biorefinery
·
2025
·
IF 4.1
Niakan Mahsa,Qian Chao,Zhou Shaodong
The conversion of 5-hydroxymethylfurfural (HMF) and carbohydrates to 5-ethoxymethylfurfural (EMF) is an attractive biomass transformation owing to the potential application of the resulting product as a fuel additive. In this work, the imidazolium hydrogen sulfate ionic liquid was grafted on the surface of silica-coated iron oxide magnetic nanoparticles using cyanuric chloride as linker, and such a magnetically separable solid acid catalyst is referred to as HSO 4 /SMNPs. The catalytic activity of HSO 4 /SMNPs was evaluated for the etherification of biomass-derived HMF with ethanol and sequential dehydration/etherification of sugars to produce EMF. The impact of various reaction parameters was studied to achieve the optimal yield of EMF. HSO 4 /SMNPs provided EMF yields of 94.3%, 68.2%, and 53.3% from HMF, fructose, and inulin in ethanol, respectively, without the need for high boiling point co-solvents. Extraordinarily, the catalyst can be readily separated from the reaction mixture by applying a permanent magnet and reused for five times without substantial activity decrease.
研究领域:
生物质化学
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催化化学
✓ 已验证
产品关联
DOI
高影响因子
CATALYSIS TODAY
·
2023
·
IF 5.3
Yong Yang,Hualei Hu,Qianquan Fang,Guowen Lu,Hongli He,Hui Chen,Chunlin Chen,Jian Zhang
The highly-efficient conversion of 5-hydroxymethylfurfural (HMF) to 2,5-bis(propoxymethyl)furan was achieved via the one-pot route, which were performed by the combination of supported copper catalyst and hierarchical pore ZSM-5 zeolite. Among the supported copper catalyst, the Cu/Al 2 O 3 catalyst exhibited the excellent activity and selectivity in the hydrogenation of HMF, obtaining a 98.7% yield of BHMF at 100 °C for 6 h under 2.5 MPa of H 2 . The reason might be attributed to that the highly dispersed copper particles and relatively weaker acid sites, which improved the hydrogenation activity of catalyst and suppressed the occurrence of side reaction. In the one-pot synthesis of BPMF, the Cu/Al 2 O 3 catalyst and HP-ZSM-5 zeolite were responsible for HMF hydrogenation and BHMF etherification , respectively, and the competition between them is negligible. This work provides a simple route to produce furanic diether from HMF.
研究领域:
化学工程
·
催化材料科学
✓ 已验证
产品关联
DOI
高影响因子
APPLIED CATALYSIS B-ENVIRONMENTAL
·
2023
·
IF 22.1
Lin Dong,Jordi Morales-Vidal,Lili Mu,Licheng Li,Núria López,Javier Pérez-Ramírez,Zupeng Chen
5-Methylfurfural (MF) is a critical commodity chemical used as food additive and synthetic intermediate. Opening a sustainable route towards highly selective synthesis of MF from 5-hydroxymethylfurfural (HMF) is of great significance, but has demonstrated extremely challenging. Herein, we report an efficient process for the selective production of MF from HMF over an anatase-supported gold catalyst (Au/a-TiO 2 ). During the hydrogenolysis of HMF, the desired C O bond is maintained and MF can be obtained in a high yield of 83.1 %, exhibiting excellent stability both in batch and flow operation. A combination of experimental and theoretical analyses attribute the superior performance of Au/a-TiO 2 to the synergistic effect of limited H access, low adsorption of reactants, and avoiding condensation, driven by the high concentration of oxygen vacancies in the support. This study highlights a novel approach of tailoring the coverage of active species for the selective transformation of renewable compounds into high-value-added chemicals.
研究领域:
化学工程
·
催化科学
·
可再生资源转化
✓ 已验证
产品关联
DOI
高影响因子
BIORESOURCE TECHNOLOGY
·
2013
·
IF 4.75
Yan Zhao,Tao Pan,Yong Zuo,Qing-Xiang Guo,Yao Fu
Catalytic pyrolysis of 5-Hydroxymethylfurfural (HMF) was conducted on a fixed bed reactor at atmospheric pressure. HMF could be converted into aromatic hydrocarbons through catalytic pyrolysis . The catalysts and reaction conditions were both critical in maximizing the aromatic hydrocarbons selectivity . Four catalysts, β-zeolite, HZSM-5, Ga/HZSM and In/HZSM were tested in this study. HZSM-5 (Si/Al = 50) was found to be the most effective catalyst in both reactivity and selectivity among these catalysts. Under the reaction temperature of 600 °C, the highest carbon yield of 48.99% of aromatic hydrocarbons was achieved from catalytic pyrolysis HMF with HZSM-5 (Si/Al = 50) as catalyst. Moreover, the HZSM-5 (Si/Al = 50) catalyst was recycled for five times without shown deactivation of the catalyst.
研究领域:
能源生物学
·
催化化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
Journal of the Taiwan Institute of Chemical Engineers
·
2016
·
IF 2.848
Fan Wang,Zehui Zhang
In this study, a new method was developed for the oxidation of 5-hydroxymethylfurfural (HMF) into 5-hydroxymethyl-2-furancarboxylic acid (HMFCA) over heterogeneous Ru catalyst. Cs-substituted tungstophosphate (CsPW) was prepared by the exchange of H + in H 3 PW 12 O 40 with Cs + , which was then used to immobilize Ru nanoparticles to give the Ru/CsPW catalyst. The Ru/CsPW catalyst was well characterized by TEM, XRD, XPS and FT-IR technologies. The physical characterizations clearly indicated that the spherica Ru nanoparticles with an average size of 2.4 nm were homogeneously dispersed on the surface of the CsPW support. The as-prepared catalyst was studied for the oxidation of HMF, and some important parameters were investigated. The reaction solvent showed a great effect on both HMF conversion and the products selectivity. Aromatic solvents were found to be the best reaction medium for the oxidation of HMF into HMFCA. Increasing the reaction temperature and the amount of the Ru/CsPW catalyst accelerated the HMF conversion and HMFCA yield. High HMF conversion of 97.2% and HMFCA yield of 72.9% were obtained after 12 h at 130 °C with oxygen flow rate of 20 ml/min. Unfortunately, the Ru/CsPW catalyst was not very stable during the reaction, and a slight loss of its catalytic activity was observed during the recycling experiments.
研究领域:
化学
·
催化材料
·
绿色化学
✓ 已验证
DOI
高影响因子
APPLIED SURFACE SCIENCE
·
2021
·
IF 6.707
Jinhua Lai,Feng Cheng,Shuolin Zhou,Sha Wen,Dongwen Guo,Wenguang Zhao,Xianxiang Liu,Dulin Yin
Nitrogen-containing polymer-supported Cu-doped MnO 2 (Cu-MnO 2 @PDVTA) nanowires were prepared and their catalytic performances were evaluated via oxidation of biomass-derived 5-hydroxymethylfurfural (HMF) to 2,5-furandicarboxylic acid (FDCA). The Cu-MnO 2 @PDVTA catalysts were characterized by Fourier-transform infrared spectroscopy, X-ray diffraction, N 2 physical adsorption, transmission electron microscopy, and X-ray photoelectron spectroscopy. Both the Cu 2+ and MnO 2 nanoparticles were found to synergistically promote HMF oxidation to FDCA via 2,5-furandicarbaldehyde and 5-formyl-2-furancarboxylic acid intermediates. The Cu-MnO 2 @PDVTA-3 catalyst demonstrated the highest catalytic activity, providing FDCA with an excellent yield of 96.8% after 12 h at 80 °C. The time course of HMF oxidation revealed that oxidation of the hydroxyl group in HMF was easier than that of the aldehyde group. Cu-MnO 2 @PDVTA-3 could act as a reusable heterogeneous catalyst for HMF oxidation.
研究领域:
化学工程
·
材料科学
·
催化反应
✓ 已验证
DOI
高影响因子
Chemical Science
·
2024
·Vol. 15
·期 28
·11043-11052
·
IF 7.6
Xingyu Lu,Ke Qi,Xueya Dai,Yunlong Li,Di Wang,Jing Dou,Wei Qi
The biomass-derived HMF oxidation reaction (HMFOR) holds great promise for sustainable production of fine chemicals. However, selective electrooxidation of HMF to high value-added intermediate product 5-formyl-furan-2-formic acid (FFCA) is still challenging. Herein, we report the electrocatalytic HMFOR to selectively produce FFCA using carbon paper (CP) supported polyaniline (PANI) as a catalyst. The PANI/CP non-metallic hybrid catalyst with moderate oxidation capacity exhibitsoptimized FFCA selectivity up to 76% in alkaline media, which has reached the best performance in reported literature studies. Identification and quantification of active sites for the HMFOR are further realized via linking the activity to structural compositions of PANI; both polaronic-type nitrogen (N3) and positively charged nitrogen (N4) species are proved responsible for adsorption and activation of HMF, and the intrinsic activity of N4 is higher than that of N3. The present work provides new physical–chemical insights into the mechanism of the HMFOR on non-metallic catalysts, paving the way for the establishment of structure–function relations and further development of novel electrochemical synthesis systems.
研究领域:
化学工程
·
材料科学
·
催化化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）