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
Sustainable Energy & Fuels
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2023
·Vol. 7
·期 9
·2209-2218
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IF 5.6
Suyan Li,Xiaoyu Hu,Yubo Li,Meiying Wang,Yu Chen,Manman Mu,Lijun Zhang
As a green and sustainable energy technology, converting solar energy into hydrogen peroxide (H2O2) chemical energy has become one of the key research fields of photocatalysis. It has been reported that TiO2 has reached an excellent H2O2 productivity of 3.3 mM h−1, and, therefore, there is value in using it for further research. Herein, a novel method for repairing and improving the surface of TiO2 was developed using small organic molecules that can enter the nanopores of TiO2 to form C, N, and O co-doped graphite-like hybrid structures. Thus, efficiently and conveniently, a multifunctional dihydropyridine with an electron-donating hydroxyl substituent successfully conducted thermally induced intermolecular condensation and subsequent in situ graphitization, resulting in efficient regulation of surficial properties. The results show that hybrid species enhanced the separation and transmission of photogenerated charges, reduced the photocatalytic effect for the decomposition of H2O2, and provided an effective channel for photocatalytic H2O2 synthesis. Under xenon lamp illumination, an initial rate of 10.22 mmol (h g)−1 H2O2 was obtained, which exceeded that for all previously reported catalysts. In addition, ACMD successfully increased the light utilization efficiency of nano-TiO2, with an apparent quantum efficiency (AQE) of 24.5% at 365 ± 5 nm and a solar-to-chemical conversion (SCC) efficiency of 2.18% under irradiation above 300 nm. Its visible light performance was significantly improved to afford 3.12 mmol (h g)−1 H2O2 with an SCC of 1.17% under irradiation greater than 420 nm. Because of the diversity of such organic molecules, this method provides researchers with many opportunities to further optimize hybrid species on the surface of TiO2, and, therefore, it is significant for the development of photocatalysts.
研究领域:
材料科学
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环境科学
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化学工程
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产品关联
DOI
高影响因子
MOLECULES
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2021
·Vol. 26
·期 7
·1925
·
IF 4.412
Xiao-Qiang Jiang,Shi-Quan Chen,Yan-Fei Liu,Xin-Guang Pan,Dan Chen,Shi-Fan Wang
Solvothermal synthesis of multiple dihydropyrimidinones at a time has been developed in inexpensive and green bio-based solvent lactic acid without any additional catalysts or additives. By this method, thirty new dihydropyrimidinone derivatives were synthesized in two batches and characterized. All of the compounds were screened by Eg5 motor protein ATPase assay, and the positive compounds were tested against the Caco-2 cell line, HeLa cell line, L929 cell line and T24 cell line in vitro. Among them, compound C9 exhibited the best inhibitory activity against motor protein ATPase with an IC50value of 30.25 μM and significant cytotoxic activity in the micromolar range against the cells above. The Lineweaver–Burk plot revealed that compound C9 was a mixed-type Eg5 inhibitor. A molecular modeling study using the Discovery Studio program was performed, where compound C9 exhibited good binding interaction with Eg5 motor protein ATPase, and this was consistent with the attained experimental results.
研究领域:
药物化学
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肿瘤学
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合成化学
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DOI
高影响因子
APPLIED ORGANOMETALLIC CHEMISTRY
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2019
·Vol. 34
·期 3
·e5454
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IF 3.259
Ningbo Li,Yijun Wang,Feijun Liu,Xin Zhao,Xinhua Xu,Quan An,Keming Yun
An air-stable complex of zirconium (IV)-salophen perfluorooctanesulfonate ( 1 ) was successfully synthesized by reacting Zr (salphen)Cl 2 and C 8 F 17 SO 3 Ag. Complex 1 was characterized and studied by different techniques (NMR, IR, HRMS, TG-DSC, conductivity and acidity measurements), and was found to be air-stable, water tolerant, thermally stable and strongly Lewis-acidic. Complex 1 exhibited high catalytic efficiency for the synthesis of 3,4-dihydropyrimidin-2-(1H)-ones/thiones via the Biginelli reaction of aldehydes, 1,3-dicarbonyl compounds and urea/thiourea under solvent-free conditions. Furthermore, complex 1 could be reused 5 times with minimal changes in catalytic efficiency. Compared with previously reported methods, the important features of this protocol are the solvent-free conditions, the short reaction times, the wide substrate compatibility, the high efficiency and the good reusability.
研究领域:
化学
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催化科学
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DOI
高影响因子
JOURNAL OF ORGANIC CHEMISTRY
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2023
·
IF 3.6
Yi Li,Yicen Ge,Rui Sun,Xiao Yang,Shipeng Huang,Huajian Dong,Yunyao Liu,Haodan Xue,Xiaoyan Ma,Haiyan Fu,Zeqin Chen
A one-pot cascade reaction for 2,3-dihydropyridinone synthesis was accomplished with 3-fluoro-2-iodo-1-methylpyridinium triflate as the halogen bond catalyst. The desired [4+2] cycloaddition products, bearing aryl, heteroaryl, alkyl, and alicyclic substituents, were successfully furnished in 28–99% yields. Mechanistic investigations proved that a strong halogen-bonding interaction forged between the iodopyridinium catalyst and imine intermediate was essential to dynamically masking the vulnerable C–I bond on the catalyst and accelerating the following aza-Diels–Alder reaction.
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
PubMed
高影响因子
LETTERS IN ORGANIC CHEMISTRY
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2023
·Vol. 20
·期 12
·1159-1169
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IF 0.8
Yaghoubi Fatemeh,imanzadeh Gholamhassan,Asgharzadeh Roghayyeh,Soltanzadeh Zahra,Öztürk Turan
Dihydropyrimidines are one of the most important heterocyclic ring systems having a serious place in medicinal and organic synthesis. In this paper, a new series of dihydropyrimidines consisting of sulfur atoms were synthesized using inorganic base K2CO3 and TBAB as an organic salt
to make high polarity in reaction media. Interestingly, different 3,4-dihydropyrimidin-2(1H)-thiones reacted smoothly with various acrylic esters to afford adducts viahighly regioselective N3-Michael addition reaction was carried out at 100°C in 12 h. result: Unfortunately, the
reaction failed with fumaric esters owing steric effects. Avoiding organic solvents during this reaction effectively led to the development of an economic approach. Structures of the new compounds were established on the basis of 1H NMR, 13C NMR, and IR spectral data.
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
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
·
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
JOURNAL OF ORGANIC CHEMISTRY
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2023
·
IF 3.6
Haiyun Peng,Yangyi Zhang,Guisheng Deng
Silver(I)-catalyzed tandem reaction of enynones with 4-alkenyl isoxazoles provides access to 2-(furan-2-yl)-1,2-dihydropyridines. No competitive cyclopropanation of alkenes and O–H insertion via (2-furyl)carbene complexes were observed. The cascade reaction proceeds via the formation of (2-furyl)metal carbene intermediate, the N–O bond cleavage of 4-alkenyl isoxazoles/rearrangement, subsequent 6π electrocyclic reaction, and [1,5] H-shift. The successive construction of both 1,2-dihydropyridine skeleton and furan frame has been achieved in the one-pot reaction. A broad range of readily available enynones and 4-alkenyl isoxazoles are suitable to this protocol; however, when R3 is the alkyl group such as n-Bu and Me, a complicated mixture was generated without the desired products. In addition, in the case of R4 = bulky group such as R3′SiOCH2, the reaction gave an in situ oxo-product of (2-furyl)silver carbene. An atom-economic strategy for the synthesis of 2-(furan-2-yl)-1,2-dihydropyridines has been established.
研究领域:
有机化学
·
合成化学
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DOI
PubMed
高影响因子
Green Processing and Synthesis
·
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
·
绿色化学
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DOI
高影响因子
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