NEW JOURNAL OF CHEMISTRY
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2023
·Vol. 47
·期 20
·9708-9713
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IF 3.3
Yuelin Xu,Fengxi Li,Yong Tang,Junhao Wu,Chunyu Wang,Chuang Du,Zhi Wang,Lei Wang
As a base structural unit, 1,4-dihydropyridines (DHPs) containing benzosultams widely exist in bioactive molecules and drugs. These compounds are generally synthesized by organic-base catalyzed methods that require specifically functionalized substrates or harsh conditions. Herein, a [3+3] annulation reaction of cyclic N-sulfonyl ketimine with various substituted isatylidene malononitrile or benzylidene malononitriles was documented. This biocatalytic strategy provides a green route for synthesis of 1,4-DHPs containing benzosultams, with good functional groups compatibility and yields. Under optimal conditions, lipase leads to the formation of 1,4-DHPs containing benzosultams in up to 87% yield.
研究领域:
有机化学
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药物化学
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生物催化
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DOI
高影响因子
CHEMICAL RESEARCH IN CHINESE UNIVERSITIES
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2019
·Vol. 35
·期 2
·235-238
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IF 1.071
Jiang Ling,Ye Wenting,Su Weike
A series of highly functionalized 1,4-dihydropyridines was synthesized via one-pot multicomponent reactions of aromatic aldehyde, malononitrile and N -methyl-1-(methylthio)-2-nitroethenamine using Porcine pancreatic lipase(PPL) as catalyst in DMSO. This protocol is featured by mild reaction conditions, simple operation and environmental acceptability.
研究领域:
有机化学
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催化化学
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绿色化学
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产品关联
DOI
高影响因子
JOURNAL OF CHEMICAL TECHNOLOGY AND BIOTECHNOLOGY
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2019
·Vol. 94
·期 8
·2555-2560
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IF 2.659
Ling Jiang,Li-dan Ye,Jia-li Gu,Wei-ke Su,Wen-ting Ye
BACKGROUND Enzyme promiscuity has attracted significant attention from chemists and biochemists in recent years. However, long reaction time and use of toxic organic solvents limit its applications for industrial processes. 1,4-Dihydropyridine (1,4-DHP) calcium antagonists are recommended for the first line treatment of hypertension. Although some chemical protocols for the preparation of 1,4-DHP calcium antagonists have been developed, enzymatic synthesis of these compounds still remains uncovered. RESULTS Solvent-free quick synthesis of 1,4-DHP calcium antagonists felodipine, nitrendipine, nifedipine and nemadipine B and their derivatives was achieved by Lipozyme® RM IM (triacylglycerol acylhydrolase, EC3.1.1.3)-catalyzed multicomponent reactions of aromatic aldehyde, alkyl acetoacetate and alkyl 3-aminocrotonate under ball-milling conditions. The products were obtained in moderate yields (up to 86.8%) and the influence of reaction conditions including catalyst loading, grinding auxiliary and grinding frequency was investigated. CONCLUSION The protocol successfully overcame some longstanding problems in the field of enzymatic promiscuity research, such as long reaction time and use of harmful organic solvents, and demonstrated the potential application value of promiscuous enzyme-catalyzed reactions under ball-milling conditions for pharmaceutical synthesis. © 2019 Society of Chemical Industry
研究领域:
药学
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生物化学
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酶工程
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产品关联
DOI
高影响因子
MONATSHEFTE FUR CHEMIE
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2016
·Vol. 147
·期 9
·1605-1614
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IF 1.131
Zhang Dawei,Chen Xiaodong,Guo Xue,Zhang Yumin,Hou Yaya,Zhao Tianqi,Gu Qiang
Abstract An efficient synthesis of 1,4-dihydropyridines was developed. 1,4-Dihydropyridines were synthesized starting from various 3-substituted isoxazolyl-5-carbaldehydes, ethyl acetoacetate, and ammonium acetate under microwave irradiation and solvent-free conditions (86–96 %), and were characterized by HRMS, FT-IR, 1 H NMR, and 13 C NMR spectroscopy. Solid support SiO 2 was found to possess favorable catalysis and dispersancy for the condensation reaction. The merits of the method included the environmental friendly reaction conditions, simple operation, extensive substrates, good yields and reuse of the SiO 2 . Moreover, the crystal structure of compound diethyl 4-[3-(2-methoxyphenyl)isoxazol-5-yl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate in orthorhombic Pbca space group was presented. Graphical abstract
研究领域:
有机化学
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药物化学
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DOI
高影响因子
MOLECULES
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2019
·Vol. 24
·期 5
·891
·
IF 3.06
Ye Liu,Jiaqi Liu,Renmei Zhang,Yan Guo,Hongbo Wang,Qingguo Meng,Yuan Sun,Zongliang Liu
3,4-dihydropyrimidin-2(1H)-one compounds (DHPMs) possess extensive biological activities and are mainly prepared via Biginelli reaction and N-alkylation. In the present study, selective alkylation of N1was investigated by using tetrabutylammonium hydroxide. In vitro cytotoxicity study on all synthesized compounds demonstrated that introduction of the aryl chain in the R3as well as the low electron-donating group in the R1of DHPMs contributed to the anti-proliferative potency. A larger value of the partition coefficient (Log P) and suitable polar surface area (PSA) values were both found to be important in order to maintain the antitumor activity. The results from in vivo study indicated the great potential of compound3dto serve as a lead compound for novel anti-tumor drugs to treat glioma. Pharmacophore study regarding the structure-activity relations of DHPMs were also conducted. Our results here could provide a guide for the design of novel bioactive 3,4-dihydropyrimidin-2(1H)-one compounds.Keywords:3,4-dihydropyrimidin-2(1H)-ones;N1-alkylation;structure-activity relationship;in vivo experiments;anticancer activities
研究领域:
药物化学
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药理学
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癌症研究
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产品关联
DOI
PubMed
高影响因子
Green Processing and Synthesis
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2019
·Vol. 8
·期 1
·568-576
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IF 1.128
Yingna Cui,Changping Li,Ming Bao
Deep eutectic solvents (DESs) are successfully used as powerful and recyclable catalysts and solvents for the synthesis of 3,4-dihydropyrimidin-2(1 H )-ones/thiones (DHPMs). The acidity of DESs is the main factor that determines catalytic activity. DESs, based on p -toluene sulfonic acid (PTSA) and choline chloride (ChCl), exhibits the highest catalytic activity. ChCl/2PTSA is suitable for a vast variety of aromatic aldehydes with electron-donating and electron-withdrawing groups, different β-diketonates, and urea or thiourea to obtain the corresponding DHPMs. Furthermore, DESs can be recycled easily after synthesis. The reused DESs achieve catalytic efficiency six times without significant changes. This study will provide a new green catalyst and efficient process for the synthesis of DHPMs.
研究领域:
有机化学
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绿色化学
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DOI
高影响因子
Nutrients
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2022
·Vol. 14
·期 19
·4090
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IF 6.706
Yilin Sun,Shengbao Cai,Yuanyue Zhang,Nan Ma,Junjie Yi,Xiaosong Hu,Tao Wang
This study focused on the preventive effects of the extracts ofRhus chinensisMill. (RCM) fruits on cholestasis induced by 3,5-diethoxycarbonyl-1,4-dihydrocollidine (DDC) in mice. The results showed that RCM extracts could significantly ameliorate DDC-induced cholestasis via multiple mechanisms, including (1) alleviating liver damage via enhancing antioxidant capacity, such as increasing the contents of glutathione, superoxide dismutase, and catalase and inhibiting the levels of malondialdehyde; (2) preventing liver inflammation by suppressing NF-κB pathway and reducing proinflammatory cytokines secretion (e.g., tumor necrosis factor-α, interleukin-1β, and interleukin-6); (3) inhibiting liver fibrosis and collagen deposition by regulating the expression of transforming growth factor-β and α-smooth muscle actin; (4) modulating abnormal bile acid metabolism through increasing the expression of bile salt export pump and multidrug resistance-associated protein 2. This study was the first to elucidate the potential preventive effect of RCM extracts on DDC-induced cholestasis in mice from multiple pathways, which suggested that RCM fruits could be considered as a potential dietary supplement to prevent cholestasis.Keywords:cholestasis;Rhus chinensisMill.;polyphenols;liver damage;oxidative stress;inflammation
研究领域:
药理学
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肝病学
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分子生物学
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产品关联
DOI
PubMed
高影响因子
MACROMOLECULES
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2025
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IF 5.2
Jingqin Yang,Yanchi Liu,Chunfeng Yin,Yuqi Lu,Yu Du,Chengxiao Wang,Shaoyun Shan,Hongying Su
There has been considerable interest in developing hydrogels derived from natural polysaccharides that combine controllable luminescent properties, enhanced functionality, and inherent biocompatibility. Herein, the classical multicomponent Hantzsch reaction was explored to fabricate luminescent dextran-based hydrogels with antibacterial activity. This reaction facilitates the formation of 1,4-dihydropyridine (DHP) derivatives from cross-linking of acetoacetylated dextran, aldehyde, and NH4OAc. Both low molecular weight aldehydes (formaldehyde and glutaraldehyde) and polyaldehyde (oxidized dextran) have been successfully applied in the Hantzsch cross-linking strategy, resulting in a series of intrinsically luminescent hydrogels (DHPD) with tunable gelation kinetic, mechanical properties, and operating windows. The DHPD hydrogels exhibited superior antibacterial activity, achieving an antimicrobial rate of over 90% against Gram-negative bacteria (Escherichia coli). Notably, significantly promoted wound healing and anti-inflammation effects were achieved in E. coli-infected wound models by the DHPD-F2 hydrogel dressing. Therefore, the Hantzsch cross-linking strategy provides a robust platform for the fabrication of photoluminescent dextran hydrogels, offering promising potential for advanced antibacterial wound dressing applications.
研究领域:
材料科学
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高分子化学
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生物医学工程
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抗菌治疗
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伤口愈合研究
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产品关联
DOI
高影响因子
CHEMICAL RESEARCH IN CHINESE UNIVERSITIES
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2019
·Vol. 35
·期 1
·21-25
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IF 1.071
Jiang Ling,Ye Wenting,Su Weike,Yu Chuanming
A new method for the synthesis of 1,4-dihydropyridine(1,4-DHP) calcium channel antagonists felodipine, nitrendipine and their derivatives via papain-catalyzed three-component reactions of aldehyde, methyl acetoacetate and ethyl 3-aminocrotonate was developed. Operational simplicity, mild reaction conditions and eco-friendliness are the key features of this protocol.
研究领域:
药物化学
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有机合成
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生物催化
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产品关联
DOI
高影响因子
JOURNAL OF ORGANIC CHEMISTRY
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2024
·
IF 3.3
Yan-Ling Liu,Xian-Chen He,Jie Gao,Ke-Rong Li,Kai Chen,Hao-Yue Xiang,Hua Yang
Herein, visible light-induced, nickel-catalyzed direct functionalization of the Hantzsch esters (HEs) with readily accessible alkyl bromides has been successfully achieved by taking advantage of HE as the reductant and substrate through an aromatization-dearomatization process. In this strategy, the single electron reduction of alkyl bromides by reactive Ni(I) species is essential for the success of this late-stage transformation. A wide range of 4-alkyl-1,4-dihydropyridines were rapidly assembled in moderate to good yields under mild conditions, rendering this photoinduced approach attractive for synthetic and medicinal chemistry.
研究领域:
有机化学
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光化学
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催化
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合成方法学
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药物化学
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DOI
高影响因子
MACROMOLECULAR CHEMISTRY AND PHYSICS
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2021
·Vol. 222
·期 23
·2100284
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IF 2.527
Da Zhang,Jinxin Zheng,Pengfei Zhang,Ronghui Zhao,Zhuo Chen,Meng Wang,Kuilin Deng
In the synthesis of traditional AIE-active polymers with conjugate or multi-benzene system, the troublesome process is still faced such as consuming time, high temperature, catalysis, no water or vacuum, and so on. In this study, the polydihydropyrimidone derivatives (PDPMDs) with AIE properties are facilely synthesized by the introduction of 4-dihydropyrimidone rings onto non-AIE-active intermediate polyureas (PUs) in Biginelli reaction. It is found that the unsymmetrical L- lysine ethyl diisocyanate and butylenediamine played a very important role in the smooth preparation and fluorescence enhancement of PDPMDs. Compared with the intermediate PUs, the fluorescence of PDPMDs is significantly enhanced (35-fold increase), which is mainly due to the intramolecular aggregation of dihydropyrimidone rings on PUs chains. At the same time, with the increase of the content of dihydropyrimidone rings, the fluorescence intensity of PDPMDs also increases, and the emission wavelength shows an obvious red shift. The fluorescence of PDPMDs also showed obvious dependence on excitation wavelength, which further reveals the clusterization-triggering emission (CTE) mechanism. In summary, the strategy of endowing AIE properties to non-AIE active polymer by introducing heterocycles into the backbone through multi-component reaction provides useful guidance for AIE functionalization of other non-AIE materials.
研究领域:
材料科学
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化学
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高分子科学
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DOI
高影响因子
JOURNAL OF COLLOID AND INTERFACE SCIENCE
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2021
·
IF 8.128
Changping Yang,Zhongwei Jiang,Qing Wu,Congyi Hu,Chengzhi Huang,Yuanfang Li,Shujun Zhen
Although a number of nanozymes have been developed, it is still difficult to develop single-component nanozyme with overall high multienzyme-like activities. In this study, the nanosized metal–organic frameworks (nano-MOFs) FePCN (PCN stands for porous coordination network) was synthesized by integrating zirconium and iron ions with different catalytic property on single-component MOFs and exhibited superior intrinsic multienzyme-like activities, namely oxidase-, peroxidase- and phosphatase-mimicking activity. The catalytic active sites of oxidase- and peroxidase-, and phosphatase-like activity of FePCN were Fe-centers and Zr-O clusters, respectively. Based on the intrinsic oxidase-like activity and the similarity of molecular structures between cytochrome P450 oxidase (CYP) cofactors and the organic linker in FePCN, FePCN exhibited high CYP-like activity to catalyze the oxidation of hypotensive drug 1,4-dihydropyridine (1,4-DHP) into diethyl 2,6-dimethylpyridine-3,5-dicarboxylate (DDPD) and the yield of DDPD reached over 80%. Moreover, as peroxidase- and phosphatase-mimics, FePCN was successfully applied to detecting H 2 O 2 under neutral condition and catalyzing the dephosphorylation of adenosine triphosphate (ATP), respectively. This study provides a feasible way for rational design one-component nanomaterials as multienzyme-mimics.
研究领域:
纳米技术
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材料科学
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生物化学
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药物化学
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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）