The authors have studied the Diels-Alder reactions between furan derivatives and maleimide derivatives in an ionic liquid and have found that higher reactivity can be obtained in a protic ionic liquid [Mim]Tf2N than i...The authors have studied the Diels-Alder reactions between furan derivatives and maleimide derivatives in an ionic liquid and have found that higher reactivity can be obtained in a protic ionic liquid [Mim]Tf2N than in the conventional organic solvent. Furthermore, in the Diels-Alder reactions of 2- and 2,5-alkylfurans with N-alkylma- leimide, the reactivity increases by extending the alkyl chain length of N-alkylmaleimide. In addition, it was demon- strated that endo-selectivity increases when 2,5-disubstituted furans are used. These results will be explained by comparing the stability of the Diels-Alder adduct with that of the products obtained from the reactions of 2-substituted furans and 2,5-disubstituted furans.展开更多
A phosphine oxide-containing bio-based curing agent was synthesized by addition reaction between furan derivatives and diphenylphosphine oxide.The molecular structure of the as-prepared bio-based curing agent was conf...A phosphine oxide-containing bio-based curing agent was synthesized by addition reaction between furan derivatives and diphenylphosphine oxide.The molecular structure of the as-prepared bio-based curing agent was confirmed by Fourier transform infrared spectroscopy and nuclear magnetic resonance spectroscopy.Dynamic mechanical analysis results indicated that with the increase of bio-based curing agent content,the glass transition temperature of epoxy/bio-based curing agent composites decreased,which was related to the steric effect of diphenylphosphine oxide species that possibly hinder the curing reaction as well as the reduction in the cross-linking density by mono-functional N-H.By the addition of 7.5 wt-%bio-based curing agent,the resulting epoxy composite achieved UL-94 V-0 rating,in addition to limiting oxygen index of 32.0 vol-%.With the increase of content for the bio-based curing agent,the peak of heat release rate and total heat release of the composites gradually decreased.The bio-based curing agent promoted the carbonization of the epoxy matrix,leading to higher char yield with good thermal resistance.The high-quality char layer served as an effective barrier to retard the diffusion of decomposition volatiles and oxygen between molten polymers and the flame.This study provides a renewable strategy for fabricating flame retardant and transparent epoxy thermoset.展开更多
A series of novel N-（3-furan-2-yl-l-phenyl-lH-pyrazol-5-yl） amides derivatives were designed and synthesized. Their structures were confirmed by 1H NMR, 13C NMR and HRMS. All title compounds were evaluated for their...A series of novel N-（3-furan-2-yl-l-phenyl-lH-pyrazol-5-yl） amides derivatives were designed and synthesized. Their structures were confirmed by 1H NMR, 13C NMR and HRMS. All title compounds were evaluated for their herbicidal and antifungal activities. Preliminary bioassay results indicated that the title compounds showed good to moderate herbicidal activity at 1000 mg/L. Compound 6q presented the best activity against Digitaria sanguinalis （L） Scop., Amaranthus retroflexus L. and Arabidopsis thaliana with an inhibition degree of five. Compound 6d also showed an inhibition degree of five against D. sanguinalis. In addition, at 50 mg/L, most compounds exhibited good in vitro antifungal activity against Sclerotinia sclerotiorum, with compound 6c showing over 90% antifungal activity against S. sclerotiorum and Pellicularia sasakii.展开更多
A facile one-pot synthesis of 3,4,5-substituted furan-2（5H）-one derivatives from a three-component reaction of aniline derivatives, dialkylacetylenedicarboxylates and aromatic aldehydes under mild conditions using t...A facile one-pot synthesis of 3,4,5-substituted furan-2（5H）-one derivatives from a three-component reaction of aniline derivatives, dialkylacetylenedicarboxylates and aromatic aldehydes under mild conditions using tetra-n-butylammonium bisulfate as a catalyst has been developed.展开更多
A series ofN-（furan-2-ylmethyl）-lH-indole-3-carboxamide derivatives（6a--6p） was designed and synthe- sized for developing novel indole scaffolds as anticancer agents targeting the epidemal growth factor receptor ...A series ofN-（furan-2-ylmethyl）-lH-indole-3-carboxamide derivatives（6a--6p） was designed and synthe- sized for developing novel indole scaffolds as anticancer agents targeting the epidemal growth factor receptor （EGFR）, and the cytotoxic activities of the target compounds were evaluated against three EGFR high-expressed cancer cell lines[human lung adenocarcinoma cell line（A549）, Henrietta Lacks strain of cancer cell line（HeLa） and human colorectal cancer cell line（SW480）], one EGFR low-expressed cell line（human liver cancer cell line, HepG2） and one human liver normal cell line（HL7702） using 3-（4,5-dimethylthiazol-2-yl）-2,5-diphenyl tetrazolium bromide （MTT） assay, Some target compounds exhibited potent anficancer activities against A549, HeLa, SW480 and weak activities on HepG2, which signifies that the target compounds are likely to be EGFR inhibitors as expected. And they showed weak cytotoxic effects on HL7702, which implies the target compounds are probably to be of low toxicity against normal cells. Among them, the target compound 1-ethyl-N-（fttran-2-ylmethyl）-5-{2-{ [2-（2-methoxy- phenoxy）ethyl]amino}-2-oxoethoxy}-2-methyl-1H-indole-3-carboxamide（6p） with 2-{[2-（2-methoxyphenoxy）ethyl]- amino}-2-oxoethoxy group at the C5 position of the N-（furan-2-ylmethyl）-lH-indole-3-carboxamide scaffold exhibited the most potent anticancer activity. Also the binding interaction of the target compound 6p with EGFR was explored by molecular docking. Conclusively, the novel indole scaffold may be beneficial to investigate new anticancer agents for targeting the EGFR.展开更多
The title compound （C16H15N3O2, Mr= 281.31） has been synthesized and characterized by elemental analysis and single-crystal X-ray diffraction. The Schiff base compound is a derivative of 4-aminoantipyrine. As expect...The title compound （C16H15N3O2, Mr= 281.31） has been synthesized and characterized by elemental analysis and single-crystal X-ray diffraction. The Schiff base compound is a derivative of 4-aminoantipyrine. As expected, the molecular structure adopts a trans configuration about the C=N double bond. It crystallizes in the monoclinic system, space group P2 1/c with a = 11.150（3）, b = 9.906（3）, c = 13.624（4） A, β = 106.360（4）°, V= 1443.9（7） ,A^3, Z = 4, Dc = 1.294 g/cm^3, F（000） = 592,μ（MoKa） = 0.088 mm ^-1, R = 0.0577 and wR = 0.1214. Of the 5766 total reflections, 2540 were unique. In the molecule there exist two different planes of pyrazoline and O（2）-C（10） phenyl ring, which are approximately coplanar （r.m.s. de deviation from the combined mean plane is 0026 A） with the dihedral angle between them of 6.3°.展开更多
文摘The authors have studied the Diels-Alder reactions between furan derivatives and maleimide derivatives in an ionic liquid and have found that higher reactivity can be obtained in a protic ionic liquid [Mim]Tf2N than in the conventional organic solvent. Furthermore, in the Diels-Alder reactions of 2- and 2,5-alkylfurans with N-alkylma- leimide, the reactivity increases by extending the alkyl chain length of N-alkylmaleimide. In addition, it was demon- strated that endo-selectivity increases when 2,5-disubstituted furans are used. These results will be explained by comparing the stability of the Diels-Alder adduct with that of the products obtained from the reactions of 2-substituted furans and 2,5-disubstituted furans.
基金the National Natural Science Fundation of China(Grant Nos.51978002 and 51403004)the Jiaxing Science and Technology Project(Grant No.2020AD10020)Postdoctoral Science Foundation of China(Grant No.2017M610399).
文摘A phosphine oxide-containing bio-based curing agent was synthesized by addition reaction between furan derivatives and diphenylphosphine oxide.The molecular structure of the as-prepared bio-based curing agent was confirmed by Fourier transform infrared spectroscopy and nuclear magnetic resonance spectroscopy.Dynamic mechanical analysis results indicated that with the increase of bio-based curing agent content,the glass transition temperature of epoxy/bio-based curing agent composites decreased,which was related to the steric effect of diphenylphosphine oxide species that possibly hinder the curing reaction as well as the reduction in the cross-linking density by mono-functional N-H.By the addition of 7.5 wt-%bio-based curing agent,the resulting epoxy composite achieved UL-94 V-0 rating,in addition to limiting oxygen index of 32.0 vol-%.With the increase of content for the bio-based curing agent,the peak of heat release rate and total heat release of the composites gradually decreased.The bio-based curing agent promoted the carbonization of the epoxy matrix,leading to higher char yield with good thermal resistance.The high-quality char layer served as an effective barrier to retard the diffusion of decomposition volatiles and oxygen between molten polymers and the flame.This study provides a renewable strategy for fabricating flame retardant and transparent epoxy thermoset.
基金financially supported by the National Natural Science Foundation of China (Nos.31171877,31571991,21372132)the International Science & Technology Cooperation Program of China (No.2014DFR41030)
文摘A series of novel N-（3-furan-2-yl-l-phenyl-lH-pyrazol-5-yl） amides derivatives were designed and synthesized. Their structures were confirmed by 1H NMR, 13C NMR and HRMS. All title compounds were evaluated for their herbicidal and antifungal activities. Preliminary bioassay results indicated that the title compounds showed good to moderate herbicidal activity at 1000 mg/L. Compound 6q presented the best activity against Digitaria sanguinalis （L） Scop., Amaranthus retroflexus L. and Arabidopsis thaliana with an inhibition degree of five. Compound 6d also showed an inhibition degree of five against D. sanguinalis. In addition, at 50 mg/L, most compounds exhibited good in vitro antifungal activity against Sclerotinia sclerotiorum, with compound 6c showing over 90% antifungal activity against S. sclerotiorum and Pellicularia sasakii.
基金fnancial support from the Research Council of the University of Sistan and Baluchestan
文摘A facile one-pot synthesis of 3,4,5-substituted furan-2（5H）-one derivatives from a three-component reaction of aniline derivatives, dialkylacetylenedicarboxylates and aromatic aldehydes under mild conditions using tetra-n-butylammonium bisulfate as a catalyst has been developed.
基金Supported by the National Natural Science Foundation of China（No.21342006） and the Program for the Innovative Research Team of the Ministry of Education of China（No.IRT_14R36）.
文摘A series ofN-（furan-2-ylmethyl）-lH-indole-3-carboxamide derivatives（6a--6p） was designed and synthe- sized for developing novel indole scaffolds as anticancer agents targeting the epidemal growth factor receptor （EGFR）, and the cytotoxic activities of the target compounds were evaluated against three EGFR high-expressed cancer cell lines[human lung adenocarcinoma cell line（A549）, Henrietta Lacks strain of cancer cell line（HeLa） and human colorectal cancer cell line（SW480）], one EGFR low-expressed cell line（human liver cancer cell line, HepG2） and one human liver normal cell line（HL7702） using 3-（4,5-dimethylthiazol-2-yl）-2,5-diphenyl tetrazolium bromide （MTT） assay, Some target compounds exhibited potent anficancer activities against A549, HeLa, SW480 and weak activities on HepG2, which signifies that the target compounds are likely to be EGFR inhibitors as expected. And they showed weak cytotoxic effects on HL7702, which implies the target compounds are probably to be of low toxicity against normal cells. Among them, the target compound 1-ethyl-N-（fttran-2-ylmethyl）-5-{2-{ [2-（2-methoxy- phenoxy）ethyl]amino}-2-oxoethoxy}-2-methyl-1H-indole-3-carboxamide（6p） with 2-{[2-（2-methoxyphenoxy）ethyl]- amino}-2-oxoethoxy group at the C5 position of the N-（furan-2-ylmethyl）-lH-indole-3-carboxamide scaffold exhibited the most potent anticancer activity. Also the binding interaction of the target compound 6p with EGFR was explored by molecular docking. Conclusively, the novel indole scaffold may be beneficial to investigate new anticancer agents for targeting the EGFR.
基金This work was supported by the Phytochemistry Key Laboratory of Shaanxi Province (No. 02js40)
文摘The title compound （C16H15N3O2, Mr= 281.31） has been synthesized and characterized by elemental analysis and single-crystal X-ray diffraction. The Schiff base compound is a derivative of 4-aminoantipyrine. As expected, the molecular structure adopts a trans configuration about the C=N double bond. It crystallizes in the monoclinic system, space group P2 1/c with a = 11.150（3）, b = 9.906（3）, c = 13.624（4） A, β = 106.360（4）°, V= 1443.9（7） ,A^3, Z = 4, Dc = 1.294 g/cm^3, F（000） = 592,μ（MoKa） = 0.088 mm ^-1, R = 0.0577 and wR = 0.1214. Of the 5766 total reflections, 2540 were unique. In the molecule there exist two different planes of pyrazoline and O（2）-C（10） phenyl ring, which are approximately coplanar （r.m.s. de deviation from the combined mean plane is 0026 A） with the dihedral angle between them of 6.3°.
