15727-49-8Relevant academic research and scientific papers
Discovery of γ-Lactam alkaloid derivatives as potential fungicidal agents targeting steroid biosynthesis
Cao, Xiufang,Huang, Daye,Huang, Wenbo,Ke, Shaoyong,Song, Di,Wang, Shuangshuang
, p. 14438 - 14451 (2020/12/23)
Biological control of plant pathogens is considered as one of the green and effective technologies using beneficial microorganisms or microbial secondary metabolites against plant diseases, and so microbial natural products have played important roles in the research and development of new and green agrochemicals. To explore the potential applications for natural γ-lactam alkaloids and their derivatives, 26 γ-lactams that have flexible substituent patterns were synthesized and characterized, and their in vitro antifungal activities against eight kinds of plant pathogens belonging to oomycetes, basidiomycetes, and deuteromycetes were fully evaluated. In addition, the high potential compounds were further tested using an in vivo assay against Phytophthora blight of pepper to verify a practical application for controlling oomycete diseases. The potential modes of action for compound D1 against Phytophthora capsici were also investigated using microscopic technology (optical microscopy, scanning electron microscopy, and transmission electron microscopy) and label-free quantitative proteomics analysis. The results demonstrated that compound D1 may be a potential novel fungicidal agent against oomycete diseases (EC50 = 4.9748 μg·mL-1 for P. capsici and EC50 = 5.1602 μg·mL-1 for Pythium aphanidermatum) that can act on steroid biosynthesis, which can provide a certain theoretical basis for the development of natural lactam derivatives as potential antifungal agents.
Method for synthesizing 1,2,3,4-tetrahydroquinoline compounds in mode that decarboxylation of amino acid is catalyzed by visible light
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Paragraph 0012, (2018/05/30)
The invention relates to a method for synthesizing 1,2,3,4-tetrahydroquinoline compounds in the mode that decarboxylation of amino acid is catalyzed by visible light. The method is characterized in that in an air atmosphere, the N-phenyl amino acidic compounds shown in the formula I, an organic photocatalyst DPZ and 4-molecular sieve are dissolved in an organic solvent, stirred and reacted for atleast 5 hours at the temperature of 20-30 DEG C under the irradiation of the visible light, separation and purification are conducted, and then the tetrahydroquinoline compounds shown in the formula II are obtained, wherein in the formula I and the formula II (the formulas are shown in the description), R is representative for any one of hydrogen, halogen, alkyl, phenyl and alkoxy, R1 is representative for any one of hydrogen, methyl, n-propyl and phenyl, alkyl is representative for methyl or ethyl or normal-butyl or benzyl, and aryl is representative for substituted phenyl or 4-tert-butyl phenyl. According to the method, substrates are simple, reaction conditions are mild, the usage amount of the catalyst is low, the yield is high, and no metal participates in a reaction.
A copper-based metal-organic framework as an efficient and reusable heterogeneous catalyst for ullmann and goldberg type C-N coupling reactions
Long, Wei,Qiu, Wenge,Guo, Chongwei,Li, Chuanqiang,Song, Liyun,Bai, Guangmei,Zhang, Guizhen,He, Hong,Kuznetsov, Maxim L.
, p. 21178 - 21192 (2016/01/25)
A highly porous metal-organic framework (Cu-TDPAT), constructed from a paddle-wheel type dinuclear copper cluster and 2,4,6-tris(3,5-dicarboxylphenylamino)-1,3,5-triazine (H6TDPAT), has been tested in Ullmann and Goldberg type C-N coupling reactions of a wide range of primary and secondary amines with halobenzenes, affording the corresponding N-arylation compounds in moderate to excellent yields. The Cu-TDPAT catalyst could be easily separated from the reaction mixtures by simple filtration, and could be reused at least five times without any significant degradation in catalytic activity.
4-Halogeno-sydnones for fast strain promoted cycloaddition with bicyclo-[6.1.0]-nonyne
Plougastel, Lucie,Koniev, Oleksandr,Specklin, Simon,Decuypere, Elodie,Créminon, Christophe,Buisson, David-Alexandre,Wagner, Alain,Kolodych, Sergii,Taran, Frédéric
supporting information, p. 9376 - 9378 (2014/08/05)
New sydnone derivatives have been synthesized and screened for their capacity to undergo fast copper-free cycloaddition reaction with bicyclo-[6.1.0]-nonyne. The influences of substitution in positions N-3 and C-4 of sydnones have been particularly studied leading to the identification of highly reactive partners for bio-orthogonal ligation reactions.
New biocatalytic route for the production of enantioenriched β-alanine derivatives starting from 5- and 6-monosubstituted dihydrouracils
Martínez-Gómez, Ana Isabel,Clemente-Jiménez, Josefa María,Rodríguez-Vico, Felipe,Kanerva, Liisa T.,Li, Xiang-Guo,Heras-Vázquez, Francisco Javier Las,Martínez-Rodríguez, Sergio
, p. 2090 - 2096 (2013/02/25)
Taking advantage of the catalytic promiscuity of pyrimidine-catabolism enzymes (dihydropyrimidinase (E.C. 3.5.2.2), N-carbamoyl-β-alanine amidohydrolase (E.C. 3.5.1.6)), the production of different β-alanine derivatives starting from 5- and 6-monosubstituted dihydrouracils has been evaluated using a mimesis approach. In this work, the S-enantioselective character of dihydropyrimidinase from Sinorizhobium meliloti toward 6-monosubstituted dihydrouracil derivatives has been shown. An inverted R-/S-enantioselectivity of N-carbamoyl-β-alanine amidohydrolase from Agrobacterium tumefaciens toward two different N-carbamoyl-β-amino acids has been proved. Our results have shown for the first time that this mimetic tandem constitutes an interesting biotechnological tool for the preparation of different β-alanine derivatives in an environmentally friendly way, allowing the production of enantioenriched (R)-α-phenyl-β-alanine (e.e. > 95%) and (R)-α-methyl-β-alanine (e.e. > 90%).
Palladium-catalyzed coupling reaction of amino acids (esters) with aryl bromides and chlorides
Ma, Fangfang,Xie, Xiaomin,Ding, Lina,Gao, Jinsheng,Zhang, Zhaoguo
scheme or table, p. 9405 - 9410 (2011/12/14)
The bulky and electron-rich MOP type ligands and Pd(dba)2 combinations showed high efficiency for the coupling reactions of amino acids and inactive aryl halides to give N-aryl amino acids. Under the catalytic conditions, not only α-amino acids, but also β-, γ-, and δ-amino acids have been coupled with aryl chlorides in moderate to high yields; in the case of optically pure β-amino acids as substrates, the optical purities of the coupling products retained.
Use of diphenyliodonium bromide in the synthesis of some N-phenyl-amino acids
McKerrow, Jason D.,Al-Rawi, Jasim M. A.,Brooks, Peter
experimental part, p. 1161 - 1179 (2010/04/28)
The N-phenyl methyl esters 4 of glycine, alanine, valine, leucine, isoleucine, phenylalanine, methionine, proline, serine, threonine, tyrosine, aspartic acid, and glutamic acid have been synthesized in good to excellent yields using diphenyliodonium bromide, AgNO3, and a catalytic amount of CuBr starting from the relevant amino acid ester. The chiral integrity of the amino acids 5 was maintained during these reactions, which were confirmed by the synthesis of dipeptide for each N-phenyl amino acid. The structures of the new compounds were confirmed by the analysis of their IR, 1H, and 13C NMR spectra in addition to CHN microanalysis or high-resolution mass spectrometry for the new N-phenyl amino acids 5 and the esters 4.
Sulfonato-Cu(salen) complex catalyzed N-arylation of aliphatic amines with aryl halides in water
Wu, Zhiqing,Zhou, Li,Jiang, Zhaoqiong,Wu, Di,Li, Zhengkai,Zhou, Xiangge
experimental part, p. 4971 - 4975 (2010/11/03)
A water-soluble sulfonato-Cu(salen) complex catalyzed procedure for the N-arylation of simple aliphatic amines, amino alcohols and amino acids in pure water have been developed. A variety of substituted aryl iodides, bromides and electron-deficient chlorides were found to be applicable, and 1,2-disubstituted benzimidazoles could be prepared easily by a cascade amination/condensation process in this catalytic system.
Copper-catalyzed aryl amination in aqueous media with 2- dimethylaminoethanol ligand
Lu, Zhikuan,Twieg, Robert J.
, p. 2997 - 3001 (2007/10/03)
Copper-catalyzed amination of aryl bromides and iodides under mild conditions has been developed with 2-dimethylaminoethanol as ligand and water as solvent. A variety of hydrophilic and hydrophobic aryl halide substrates have been aminated in good yield with a variety of amino acids, amino alcohols and peptides. This method has successfully N-arylated some hydrophilic amino compounds not available by other methods.
Microbial deracemization of α-substituted carboxylic acids: Control of the reaction path
Kato, Dai-Ichiro,Miyamoto, Kenji,Ohta, Hiromichi
, p. 2965 - 2973 (2007/10/03)
A novel approach to preparing optically active α-substituted carboxylic acids using the whole cells of Nocardia diaphanozonaria JCM 3208 is described. When 2-phenylthiopropanoic acid and 2-methyl-3-phenylpropanoic acid were subjected to the reaction under aerobic conditions, the oxidation reaction proceeded preferentially rather than deracemization of these substrates. Herein, we report the design of reaction conditions to increase the deracemization activity in preference to oxidation reactions. In addition, we have successfully detected a metabolic intermediate in the reaction mixture of 2-methyl-3-phenylpropanoic acid, which indicates that the deracemization is a competitive reaction against the α-oxidation pathway of fatty acid metabolism.
