The Passerini three-component reaction of carboxylic acid, aromatic aldehyde and isocyanide was carried out smoothly and efficiently in ionic liquid [bmim]BF4. Through this reaction, a series of α-acyloxycarboxamides...The Passerini three-component reaction of carboxylic acid, aromatic aldehyde and isocyanide was carried out smoothly and efficiently in ionic liquid [bmim]BF4. Through this reaction, a series of α-acyloxycarboxamides were obtained in high yields. Advantages of this proccedure include a green nature, high efficiency and operational simplicity展开更多
L-glutamic acid(LA)is a bio-based,non-toxic,environmentally friendly material derived from biomass.The present study reports the application of Passerini three-component polymerization(P-3CP)for the straightforward pr...L-glutamic acid(LA)is a bio-based,non-toxic,environmentally friendly material derived from biomass.The present study reports the application of Passerini three-component polymerization(P-3CP)for the straightforward preparation of LA-based light-responsive polyesters(PLTDs)under mild conditions.PLTDs with molar masses up to 8500 g/mol and high yields exceeding 90%are obtained.The chemical structures and light-responsive self-immolative behavior of PLTDs are comprehensively characterized by employing ultraviolet-visible(UV-Vis)spectroscopy,size exclusion chromatography(SEC),nuclear magnetic resonance(NMR)spectroscopy,and liquid chromatography mass spectrometry(LC-MS).Meanwhile,monodisperse PLTD-based doxorubicin-loaded nanoparticles(PLTD-DOX-NP)(size=193 nm,PDI=0.018)are formulated by nanoprecipitation method.Upon light-induced depolymerization,the PLTD-DOX-NP undergoes rapid decomposition,resulting in a burst release of 80%cargo within 13 s.Furthermore,according to biological toxicity tests,the PLTD-NP possesses adequate biosafety,both before and after irradiation.Overall,the incorporation of P-3CP with biorenewable LA-based monomer adheres to the principles of green chemistry,significantly simplifying the synthetic pathway of light-responsive polymers.展开更多
A green Passerini three-component reaction of 2-（4-oxo-4,5,6,7-tetrahydro-1H-indol-1-yl）acetic acid with alkyl or aryl isocyanides and aldehydes was reported under aqueous conditions at 35 ℃ for 1 h, and21 indolone...A green Passerini three-component reaction of 2-（4-oxo-4,5,6,7-tetrahydro-1H-indol-1-yl）acetic acid with alkyl or aryl isocyanides and aldehydes was reported under aqueous conditions at 35 ℃ for 1 h, and21 indolone-N-amino acid derivatives were prepared in high yields of 42%–99%. Their structures were characterized by IR, ESI–MS, NMR and elemental analysis, and the possible mechanisms have been also proposed. The highly efficient and eco-friendly method provides a facile access to a library of indoloneN-amino acid derivatives for future research on bioactivity screening.展开更多
α-Acyloxycarboxamides are synthesized from three-component Passerini reaction between indane-1,2,3-trione, isocyanides, and thiophenecarboxylic acids in quantitative yields. The structures of the final products were ...α-Acyloxycarboxamides are synthesized from three-component Passerini reaction between indane-1,2,3-trione, isocyanides, and thiophenecarboxylic acids in quantitative yields. The structures of the final products were confirmed by IR, 1H and 13C NMR spectroscopy, mass spectrometry, and elemental analysis. The B3LYP/HF calculations for computation of 1H and 13C NMR chemical shifts have been carried out for the title compounds at the 6-311＋G＊＊ and 6-311＋＋G＊＊ basis set levels within GIAO and CSGT approaches. Predicted 1H and 13C NMR che-mical shifts have been assigned and compared with experimental 1H and 13C NMR spectra and they are supported each other.展开更多
Two amphiphilic macromolecules were synthesized from polyethylene glycol monomethylether（PEG）and borondipyrrolmethene（BODIPY） via one-pot multicomponent Passerini reaction,and they could self-assemble into stable ...Two amphiphilic macromolecules were synthesized from polyethylene glycol monomethylether（PEG）and borondipyrrolmethene（BODIPY） via one-pot multicomponent Passerini reaction,and they could self-assemble into stable nanoparticles（NPs） in aqueous media.The optical properties,including fluorescence resonance energy transfer（FRET） were studied in detail.The obtained NPs possess good cytocompatibility,and could be used for living cell imaging and effective photodynamic therapy（PDT）.These results shed light on one-pot synthesis of PEGylated fluorescent nanoparticles via multicomponent reaction for biomedical application.展开更多
Dysregulated HGF/c-Met signalling has been associated with many human cancers,poor clinical outcomes,and even resistance acquisition to some approved targeted therapies.As such,c-Met kinase has emerged as an attractiv...Dysregulated HGF/c-Met signalling has been associated with many human cancers,poor clinical outcomes,and even resistance acquisition to some approved targeted therapies.As such,c-Met kinase has emerged as an attractive target for anticancer drug discovery.展开更多
Multicomponent polymerizations have become powerful tools for the construction of sequence-defined polymers. Although the Passerini multicomponent reaction has been widely used in the synthesis of sequence-defined pol...Multicomponent polymerizations have become powerful tools for the construction of sequence-defined polymers. Although the Passerini multicomponent reaction has been widely used in the synthesis of sequence-defined polymers, the tandem usage of the Passerini multicomponent reaction and other multicomponent reactions in one-pot for the synthesis of sequence-defined polymers has not been developed until now. In this contribution, we report the tandem usage of the Passerini three-component reaction and the three-component amine-thiol-ene conjugation reaction in one pot for the synthesis of sequence-defined polymers. The Passerini reaction between methacrylic acid, adipaldehyde, and 2-isocyanobutanoate was carried out, affording a new molecule containing two alkene units. Subsequently, an amine and a thiolactone were added to the reaction system, whereupon the three-component amine-thiol-ene conjugating reaction occurred to yield a sequence-defined polymer. This method offers more rapid access to sequence-defined polymers with high molecular diversity and complexity.展开更多
文摘The Passerini three-component reaction of carboxylic acid, aromatic aldehyde and isocyanide was carried out smoothly and efficiently in ionic liquid [bmim]BF4. Through this reaction, a series of α-acyloxycarboxamides were obtained in high yields. Advantages of this proccedure include a green nature, high efficiency and operational simplicity
基金This work was financially supported by the International Science and Technology Assistance Program of the Ministry of Science and Technology(No.KY202001016)Shandong Provincial Natural Science Foundation Magnitude Fundamental Research,China(No.ZR2022ZD11)Qingdao New Energy Shandong Laboratory Open Project(No.QNESL OP202312).
文摘L-glutamic acid(LA)is a bio-based,non-toxic,environmentally friendly material derived from biomass.The present study reports the application of Passerini three-component polymerization(P-3CP)for the straightforward preparation of LA-based light-responsive polyesters(PLTDs)under mild conditions.PLTDs with molar masses up to 8500 g/mol and high yields exceeding 90%are obtained.The chemical structures and light-responsive self-immolative behavior of PLTDs are comprehensively characterized by employing ultraviolet-visible(UV-Vis)spectroscopy,size exclusion chromatography(SEC),nuclear magnetic resonance(NMR)spectroscopy,and liquid chromatography mass spectrometry(LC-MS).Meanwhile,monodisperse PLTD-based doxorubicin-loaded nanoparticles(PLTD-DOX-NP)(size=193 nm,PDI=0.018)are formulated by nanoprecipitation method.Upon light-induced depolymerization,the PLTD-DOX-NP undergoes rapid decomposition,resulting in a burst release of 80%cargo within 13 s.Furthermore,according to biological toxicity tests,the PLTD-NP possesses adequate biosafety,both before and after irradiation.Overall,the incorporation of P-3CP with biorenewable LA-based monomer adheres to the principles of green chemistry,significantly simplifying the synthetic pathway of light-responsive polymers.
基金the financial support by the Natural Science Foundation of China(No.21272136)Scientific Foundation from graduate school(2015PY089)Youth Talent Development Foundation of China Three Gorges University
文摘A green Passerini three-component reaction of 2-（4-oxo-4,5,6,7-tetrahydro-1H-indol-1-yl）acetic acid with alkyl or aryl isocyanides and aldehydes was reported under aqueous conditions at 35 ℃ for 1 h, and21 indolone-N-amino acid derivatives were prepared in high yields of 42%–99%. Their structures were characterized by IR, ESI–MS, NMR and elemental analysis, and the possible mechanisms have been also proposed. The highly efficient and eco-friendly method provides a facile access to a library of indoloneN-amino acid derivatives for future research on bioactivity screening.
文摘α-Acyloxycarboxamides are synthesized from three-component Passerini reaction between indane-1,2,3-trione, isocyanides, and thiophenecarboxylic acids in quantitative yields. The structures of the final products were confirmed by IR, 1H and 13C NMR spectroscopy, mass spectrometry, and elemental analysis. The B3LYP/HF calculations for computation of 1H and 13C NMR chemical shifts have been carried out for the title compounds at the 6-311＋G＊＊ and 6-311＋＋G＊＊ basis set levels within GIAO and CSGT approaches. Predicted 1H and 13C NMR che-mical shifts have been assigned and compared with experimental 1H and 13C NMR spectra and they are supported each other.
基金supported by the National Natural Science Foundation of China(Nos.51522307 and 81673396)
文摘Two amphiphilic macromolecules were synthesized from polyethylene glycol monomethylether（PEG）and borondipyrrolmethene（BODIPY） via one-pot multicomponent Passerini reaction,and they could self-assemble into stable nanoparticles（NPs） in aqueous media.The optical properties,including fluorescence resonance energy transfer（FRET） were studied in detail.The obtained NPs possess good cytocompatibility,and could be used for living cell imaging and effective photodynamic therapy（PDT）.These results shed light on one-pot synthesis of PEGylated fluorescent nanoparticles via multicomponent reaction for biomedical application.
基金This work was supported by the Fundamental Research Funds for the Central Universities(Nos.31920170193 and 31920200026).
文摘Dysregulated HGF/c-Met signalling has been associated with many human cancers,poor clinical outcomes,and even resistance acquisition to some approved targeted therapies.As such,c-Met kinase has emerged as an attractive target for anticancer drug discovery.
基金supported by the National Natural Science Foundation of China(51273187,21374107)the Fundamental Research Funds for the Central Universities(WK2060200012)the Program for New Century Excellent Talents in Universities(NCET-11-0882)
文摘Multicomponent polymerizations have become powerful tools for the construction of sequence-defined polymers. Although the Passerini multicomponent reaction has been widely used in the synthesis of sequence-defined polymers, the tandem usage of the Passerini multicomponent reaction and other multicomponent reactions in one-pot for the synthesis of sequence-defined polymers has not been developed until now. In this contribution, we report the tandem usage of the Passerini three-component reaction and the three-component amine-thiol-ene conjugation reaction in one pot for the synthesis of sequence-defined polymers. The Passerini reaction between methacrylic acid, adipaldehyde, and 2-isocyanobutanoate was carried out, affording a new molecule containing two alkene units. Subsequently, an amine and a thiolactone were added to the reaction system, whereupon the three-component amine-thiol-ene conjugating reaction occurred to yield a sequence-defined polymer. This method offers more rapid access to sequence-defined polymers with high molecular diversity and complexity.
