The two diarylheptanoids (E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl) hept-4-en-3-one 1 (Gingerenone C) and (±)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-7-(4- hydroxyphenyl)-3-heptanone 2 were synthesized...The two diarylheptanoids (E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl) hept-4-en-3-one 1 (Gingerenone C) and (±)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-7-(4- hydroxyphenyl)-3-heptanone 2 were synthesized from vanillin 3 and 4-hydroxybenzaldehyde 9.展开更多
2-(4-Hydroxyphenyl)-3-hydroxymethyl-1,4-benzodioxane-6-aldehyde 8,the key intermediate of sinaiticin 10,was synthesized in 6 step from caffeic acid 4 and 4- hydroxybenzsaldehyde 1.the coupling reaction is the key step.
A facile synthesis of the analog of curcumin. 1,7-bis (4-hydroxyphenyl)-3-hydroxy-1.3-heptadien-5-one 1 was achieved. The key step was completed through the regioselective condensation of ketone 5 and acyl chloride 7.
A new quinazolinone compound 2,3-dihydro-2-(2-hydroxyphenyl)-3-phenyl- quinazolin-4(1H)-one 3 ([C20H16O2N2]?C2H5OH, Mr = 362.42) and compound 2-(2-hydroxy- benzylidene-amino)-N-phenyl-benzamide 2 (C20H16O2N2, Mr = 316...A new quinazolinone compound 2,3-dihydro-2-(2-hydroxyphenyl)-3-phenyl- quinazolin-4(1H)-one 3 ([C20H16O2N2]?C2H5OH, Mr = 362.42) and compound 2-(2-hydroxy- benzylidene-amino)-N-phenyl-benzamide 2 (C20H16O2N2, Mr = 316.34) were prepared from a precursor of 2-amino-N-phenyl-benzamide 1 (C13H12ON2, Mr = 212.25). Compound 3 was characterized by single-crystal X-ray diffraction analysis. The crystal belongs to orthorhombic, space group Pbca with a = 1.2889(11), b = 1.6170(14), c = 1.7729(15) nm, V = 3.695(6) nm3, Z = 8, F(000) = 1536, Mr = 362.42, Dc = 1.303 g/cm3, μ(MoKα) = 0.087 mm-1, R = 0.0447 and wR = 0.0879. The crystal structure analysis indicates that the title compound has a two-dimensional network structure formed by hydrogen bonds and electrostatic interactions.展开更多
Results of oxidation 2-(N-acetylamine)-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionic acid oxygen depend on temperature. At 55℃?- 60℃, 2,4-di-tert-butylbicyclo(4,3,1)deca-4,6-dien-8-(N-acetylamine)-3,9-dion-1-oxa i...Results of oxidation 2-(N-acetylamine)-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionic acid oxygen depend on temperature. At 55℃?- 60℃, 2,4-di-tert-butylbicyclo(4,3,1)deca-4,6-dien-8-(N-acetylamine)-3,9-dion-1-oxa is formed. The constitution is based on dates of spectrums 1Н and 13С NMR. At 95℃?- 97℃, mixtures of 2,4-di-tert-butylbicyclo(4,3,1)deca-4,6-dien-8-(N-acetylamine)-3,9-dion-1-oxa and of 6,8-di-tert-butyl-3-(N-acetylamine)spiro(4,5)deca-1-oxa-5,8-dien-2,7-dione are produced. Structures are calculated by the method of Hartrii-Foka. Values of enthalpies and of entropies allow to assume dynamic isomerism.展开更多
3-（4-Hydroxyphenyl）-4-methyl-6-methoxy-7-hydroxycoumarin （2a） and its analogues with different substituents at the p-position of 3-phenyl group were designed and synthesized as the non-steroidal analogues of 2-met...3-（4-Hydroxyphenyl）-4-methyl-6-methoxy-7-hydroxycoumarin （2a） and its analogues with different substituents at the p-position of 3-phenyl group were designed and synthesized as the non-steroidal analogues of 2-methoxyestradiol （2-ME 1）. The desired compounds were synthesized via a novel and simple route and the effects of specific substituents on their antiangiogenesis activities were investigated with Human umbilical vein endothelial cells （HUVECs） proliferation assays. Preliminary biological screening showed that compounds 2a and 2d （IC50 = 61.0 and 76.7 ktM, respectively） have potential anti-angiogenesis activities. The bulk of the group at the p-position of 3-phenyl group likely play an important role in their activities.展开更多
Objective： To study apoptotic effects of synthetic retinoic acid 6-[3-（1-adamantyl）-4-hydroxyphenyl]-2-naphthalene carboxylic acid（AHPN） on human skin malignant melanoma A375 cells in comparison with the natural ...Objective： To study apoptotic effects of synthetic retinoic acid 6-[3-（1-adamantyl）-4-hydroxyphenyl]-2-naphthalene carboxylic acid（AHPN） on human skin malignant melanoma A375 cells in comparison with the natural ligand all-trans-retinoic acid（ATRA） in vitro and the mechanisms related to the actions of AHPN. Methods：MTT assay was used to determine the anti-proliferative effects of AHPN and ATRA on A375 cells. Flow cytometry was performed to investigate the influence of AHPN and ATRA on cell cycle and cell apoptosis. In addition, transfection and luciferase activity assays were employed to explore the mechanisms of how AHPN executes its proapoptotic function. Results：Firstly, AHPN promoted apoptosis and GI arrest in A375 cells compared with ATRA. Secondly, the activity of NF-K B in A375 cells treated with AHPN increased 2-3 times compared with solvent DMSO treatment. Conclusion：AHPN, in comparison with ATRA, is a more effective alternative for therapy of malignant melanoma. The potentially proapoptotic function of AHPN requires activation of NF-K B.展开更多
A new quinolizidine alkaloid. 3-(4-hydroxyphenyl)-4-(3-methoxy-4-hydroxyphenyl)-3,4-dihydroquinolizidine (1). was isolated from the ethanol extract of the whole plants of Boehmeria siamensis Craib. Its structure was e...A new quinolizidine alkaloid. 3-(4-hydroxyphenyl)-4-(3-methoxy-4-hydroxyphenyl)-3,4-dihydroquinolizidine (1). was isolated from the ethanol extract of the whole plants of Boehmeria siamensis Craib. Its structure was elucidated on the analysis of ID NMR and 2D NMR spectrum.展开更多
A new chromone derivative, 3-[1- (2, 4, 6-trihydroxyphenyl) 3-di-(4-hydroxyphenyl) 1-propanone-2-yl] 5,7-dihydroxy-8-di(4-hydroxyphenyl)methyl-4H-1-benzopyran-4-one, named as isomohsenone was isolated from the roots o...A new chromone derivative, 3-[1- (2, 4, 6-trihydroxyphenyl) 3-di-(4-hydroxyphenyl) 1-propanone-2-yl] 5,7-dihydroxy-8-di(4-hydroxyphenyl)methyl-4H-1-benzopyran-4-one, named as isomohsenone was isolated from the roots of Stellera chamaejasme L. together with known chamaechromone. Its structure was determined by the analysis of MS and NMR data, especially 2D NMR spectra.展开更多
In present literature search, some cyano-containing compounds, which are very rare in plants, from the traditional anticancer herb Tiankuizi were reported. To find more cyano-containing compounds in the important plan...In present literature search, some cyano-containing compounds, which are very rare in plants, from the traditional anticancer herb Tiankuizi were reported. To find more cyano-containing compounds in the important plant Semiaquilegia adoxoides （DC） Makino （Chinese name Tiankuizi）, the isolation of the chemical constituents was investigated for advancing the research. Two new compounds, a new alkaloid, 1,2,3,4-tetrahydro-6-hydroxy-1[（3,4-dihydroxyphenyl）methyl]-7-methoxy-2,2-dimethyl-isoquinolinium, named Semiaquilegine A （1）, and a new ester, 3-（4＇-hydroxyphenyl）-2-propenoic acid （4＂-carboxyl）-phenyl ester （2）, and four cyano-containing compounds, （Z）-6a-（β-D-glucosyloxy）-4a,5a-dihydroxy-2-cyclohexene-△^1,a-acetonitrile （3）, （L0-6α-（β-D-glucosyloxy）-4α-hydroxy-2-cyclohexene-△^1,α-acetonitrile （4）, lithospermoside （5）, ehretioside B （6）, as well as eleven known compounds, were isolated from the roots of Semiaquilegia adoxoides. The structures of new compounds 1 and 2 were elucidated mainly by 1D/2D-NMR techniques. Very unusual cyano-containing compounds 3 and 4 were first isolated from Ranunculaceae family. Hitherto, there were six cyano-containing compounds found in the herb.展开更多
文摘The two diarylheptanoids (E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl) hept-4-en-3-one 1 (Gingerenone C) and (±)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-7-(4- hydroxyphenyl)-3-heptanone 2 were synthesized from vanillin 3 and 4-hydroxybenzaldehyde 9.
文摘2-(4-Hydroxyphenyl)-3-hydroxymethyl-1,4-benzodioxane-6-aldehyde 8,the key intermediate of sinaiticin 10,was synthesized in 6 step from caffeic acid 4 and 4- hydroxybenzsaldehyde 1.the coupling reaction is the key step.
文摘A facile synthesis of the analog of curcumin. 1,7-bis (4-hydroxyphenyl)-3-hydroxy-1.3-heptadien-5-one 1 was achieved. The key step was completed through the regioselective condensation of ketone 5 and acyl chloride 7.
基金This project was supported by the NNSFC (No. 20371039), National Basic Research Program of China (the 973 Program, No. 2003CB214606), and the Key Laboratory Research and Establishment Program and NSF of Department of Education of Shaanxi Province (No. 03JS006 and No. 04JK143)
文摘A new quinazolinone compound 2,3-dihydro-2-(2-hydroxyphenyl)-3-phenyl- quinazolin-4(1H)-one 3 ([C20H16O2N2]?C2H5OH, Mr = 362.42) and compound 2-(2-hydroxy- benzylidene-amino)-N-phenyl-benzamide 2 (C20H16O2N2, Mr = 316.34) were prepared from a precursor of 2-amino-N-phenyl-benzamide 1 (C13H12ON2, Mr = 212.25). Compound 3 was characterized by single-crystal X-ray diffraction analysis. The crystal belongs to orthorhombic, space group Pbca with a = 1.2889(11), b = 1.6170(14), c = 1.7729(15) nm, V = 3.695(6) nm3, Z = 8, F(000) = 1536, Mr = 362.42, Dc = 1.303 g/cm3, μ(MoKα) = 0.087 mm-1, R = 0.0447 and wR = 0.0879. The crystal structure analysis indicates that the title compound has a two-dimensional network structure formed by hydrogen bonds and electrostatic interactions.
文摘Results of oxidation 2-(N-acetylamine)-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionic acid oxygen depend on temperature. At 55℃?- 60℃, 2,4-di-tert-butylbicyclo(4,3,1)deca-4,6-dien-8-(N-acetylamine)-3,9-dion-1-oxa is formed. The constitution is based on dates of spectrums 1Н and 13С NMR. At 95℃?- 97℃, mixtures of 2,4-di-tert-butylbicyclo(4,3,1)deca-4,6-dien-8-(N-acetylamine)-3,9-dion-1-oxa and of 6,8-di-tert-butyl-3-(N-acetylamine)spiro(4,5)deca-1-oxa-5,8-dien-2,7-dione are produced. Structures are calculated by the method of Hartrii-Foka. Values of enthalpies and of entropies allow to assume dynamic isomerism.
文摘3-（4-Hydroxyphenyl）-4-methyl-6-methoxy-7-hydroxycoumarin （2a） and its analogues with different substituents at the p-position of 3-phenyl group were designed and synthesized as the non-steroidal analogues of 2-methoxyestradiol （2-ME 1）. The desired compounds were synthesized via a novel and simple route and the effects of specific substituents on their antiangiogenesis activities were investigated with Human umbilical vein endothelial cells （HUVECs） proliferation assays. Preliminary biological screening showed that compounds 2a and 2d （IC50 = 61.0 and 76.7 ktM, respectively） have potential anti-angiogenesis activities. The bulk of the group at the p-position of 3-phenyl group likely play an important role in their activities.
文摘Objective： To study apoptotic effects of synthetic retinoic acid 6-[3-（1-adamantyl）-4-hydroxyphenyl]-2-naphthalene carboxylic acid（AHPN） on human skin malignant melanoma A375 cells in comparison with the natural ligand all-trans-retinoic acid（ATRA） in vitro and the mechanisms related to the actions of AHPN. Methods：MTT assay was used to determine the anti-proliferative effects of AHPN and ATRA on A375 cells. Flow cytometry was performed to investigate the influence of AHPN and ATRA on cell cycle and cell apoptosis. In addition, transfection and luciferase activity assays were employed to explore the mechanisms of how AHPN executes its proapoptotic function. Results：Firstly, AHPN promoted apoptosis and GI arrest in A375 cells compared with ATRA. Secondly, the activity of NF-K B in A375 cells treated with AHPN increased 2-3 times compared with solvent DMSO treatment. Conclusion：AHPN, in comparison with ATRA, is a more effective alternative for therapy of malignant melanoma. The potentially proapoptotic function of AHPN requires activation of NF-K B.
文摘A new quinolizidine alkaloid. 3-(4-hydroxyphenyl)-4-(3-methoxy-4-hydroxyphenyl)-3,4-dihydroquinolizidine (1). was isolated from the ethanol extract of the whole plants of Boehmeria siamensis Craib. Its structure was elucidated on the analysis of ID NMR and 2D NMR spectrum.
文摘A new chromone derivative, 3-[1- (2, 4, 6-trihydroxyphenyl) 3-di-(4-hydroxyphenyl) 1-propanone-2-yl] 5,7-dihydroxy-8-di(4-hydroxyphenyl)methyl-4H-1-benzopyran-4-one, named as isomohsenone was isolated from the roots of Stellera chamaejasme L. together with known chamaechromone. Its structure was determined by the analysis of MS and NMR data, especially 2D NMR spectra.
文摘In present literature search, some cyano-containing compounds, which are very rare in plants, from the traditional anticancer herb Tiankuizi were reported. To find more cyano-containing compounds in the important plant Semiaquilegia adoxoides （DC） Makino （Chinese name Tiankuizi）, the isolation of the chemical constituents was investigated for advancing the research. Two new compounds, a new alkaloid, 1,2,3,4-tetrahydro-6-hydroxy-1[（3,4-dihydroxyphenyl）methyl]-7-methoxy-2,2-dimethyl-isoquinolinium, named Semiaquilegine A （1）, and a new ester, 3-（4＇-hydroxyphenyl）-2-propenoic acid （4＂-carboxyl）-phenyl ester （2）, and four cyano-containing compounds, （Z）-6a-（β-D-glucosyloxy）-4a,5a-dihydroxy-2-cyclohexene-△^1,a-acetonitrile （3）, （L0-6α-（β-D-glucosyloxy）-4α-hydroxy-2-cyclohexene-△^1,α-acetonitrile （4）, lithospermoside （5）, ehretioside B （6）, as well as eleven known compounds, were isolated from the roots of Semiaquilegia adoxoides. The structures of new compounds 1 and 2 were elucidated mainly by 1D/2D-NMR techniques. Very unusual cyano-containing compounds 3 and 4 were first isolated from Ranunculaceae family. Hitherto, there were six cyano-containing compounds found in the herb.
