One novel spirolactone,aquilarisinolide(1),three new sesquiterpenoids,(2R,4S,5R,7R)-2-hydroxyeremophila-9,11-dien-8-one(2),(1R,4S,5S,7R,11R)-13-hydroxyepidaphnauran-9-en-8-one(3),and(4R,5S,7R,8S,10S,13R)-8,13-dihydrox...One novel spirolactone,aquilarisinolide(1),three new sesquiterpenoids,(2R,4S,5R,7R)-2-hydroxyeremophila-9,11-dien-8-one(2),(1R,4S,5S,7R,11R)-13-hydroxyepidaphnauran-9-en-8-one(3),and(4R,5S,7R,8S,10S,13R)-8,13-dihydroxyrotunda-1,11-dien-3-one(4),together with 13 known compounds(5-17)were isolated from the resinous heartwood of Aquilaria sinensis(Thymelaeaceae).The structures of the new compounds were elucidated based on the analysis of NMR and MS data and theoretical calculations their ECD spectra.The isolated compounds were evaluated for their protective activities against PC12 cell injury induced by corticosterone(CORT)and 1-methyl-4-phenylpyridine ion(MPP+),as well as inhibitory activities against BACE1.Compound 4,5,6-dihydroxy-2-(2-phenylethyl)chromone(5),daphnauranol B(7),6-methoxy-2-[2-(3-methyoxyphenyl)ethyl]chromone(10),isoagarotetrol(14),and 1-hydroxy-1,5-diphenylpentan-3-one(16)showed significant protective effects on CORT-induced injury in PC12 cells at a concentration of 20μM(P<0.001).Isoagarotetrol(14)showed a significant protective effect on MPP+-induced injury in PC12 cells at a concentration of 20μM(P<0.001),while compound 4 showed a moderate activity(P<0.01).The BACE1-inhibitory activities of all tested compounds were very weak with less than 30%inhibition at a concentration of 20μM.展开更多
Five new 2-(2-phenylethyl)chromone derivatives,(5S,6R,7R,8S,7ʹR)-7ʹ-hydroxyagarotetrol(1),(5S,6R,7R,8S,7ʹS)-7ʹ-hydroxyagarotetrol(2),(6S,7S,8R)-2-[2-(4-methoxyphenyl)ethyl]-6,7,8-trihydroxy-5,6,7,8-tetrahydrochromone(...Five new 2-(2-phenylethyl)chromone derivatives,(5S,6R,7R,8S,7ʹR)-7ʹ-hydroxyagarotetrol(1),(5S,6R,7R,8S,7ʹS)-7ʹ-hydroxyagarotetrol(2),(6S,7S,8R)-2-[2-(4-methoxyphenyl)ethyl]-6,7,8-trihydroxy-5,6,7,8-tetrahydrochromone(3),(6S,7S,8R)-2-(2-phenylethyl)-6,7,8-trihydroxy-5,6,7,8-tetrahydrochromone(4),(5S,6R,7S,8R)-2-(2-phenylethyl)-5,6,7-trihydroxy-5,6,7,8-tetrahydro-8-[2-(2-phenylethyl)-7-methoxychromonyl-6-oxy]chromone(5),three new sesquiterpenoids,(4S,5S,7S,8S,10S,13R)-7,8,13-trihydroxyrotunda-1,11-dien-3-one(6),(4S,5S,7S,8S,10S,13S)-7,8,13-trihydroxyrotunda-1,11-dien-3-one(7),and(4R,5S,7S,8S,10S,13S)-7,8,13-trihydroxyrotunda-1,11-dien-3-one(8),along with 14 known compounds were isolated from the resinous heartwood of Aquilaria sinensis(Thymelaeaceae).The chemical structures of these new compounds were elucidated by 1D and 2D NMR and MS data,single-crystal X-ray diffraction analysis,and electronic circular dichroism(ECD)calculations.The neuroprotective activities of these isolates were evaluated using an in vitro model of rat adrenal pheochromocytoma(PC12)cell injury induced by corticosterone.At concentrations from 5 to 40μM,compounds 4 and 6,agarotetrol(9),and 6-hydroxy-2-(2-phenylethyl)chromone(17)showed significant protective activities against corticosterone-induced PC12 cell injury(P<0.001).展开更多
5-Hydroxy-2-(2-phenylethyl)chromone(l) was synthesized from 2,6-dihydroxyacetophenone(7) obtained via four-steps resorcinol-reacting with phenylpropionic acid, the procedures involved are Baker-Venkataraman rear...5-Hydroxy-2-(2-phenylethyl)chromone(l) was synthesized from 2,6-dihydroxyacetophenone(7) obtained via four-steps resorcinol-reacting with phenylpropionic acid, the procedures involved are Baker-Venkataraman rear-rangement and cyclization which are easy to conduct, the overall yield is 32%.展开更多
Nine 3,3’-(arylmethylene)bis(2-hydroxynaphthalene-1,4-dione) derivatives were synthesized through the reaction between 2-hydroxy-1,4-naphthalen-1,4-dione and different aromatic alde-hydes in water applying ultrasonic...Nine 3,3’-(arylmethylene)bis(2-hydroxynaphthalene-1,4-dione) derivatives were synthesized through the reaction between 2-hydroxy-1,4-naphthalen-1,4-dione and different aromatic alde-hydes in water applying ultrasonic irradiation for 5 min at room temperature and microwave irradiation for 15 min at 70°;C. Two of the nine derivatives, compounds 3-e and 3-i, obtained from 3-bromo-hydroxybenzaldehyde and 5-methylfuran-2-carbaldehyde, respectively, are previously unpublished. The structures of all compounds were established on the basis of their spectral data and mass analysis. The attractive features of this synthesis protocol include mild conditions, high atom-economy and excellent yields with the elimination of water as the only by-product.展开更多
The quantitative structure-activity relationship (QSAR) of 14 phenoxybenzoic acid derivatives was studied by ab initio method at the HF/6-31G level using Guassian03 software. The optimized structures together with s...The quantitative structure-activity relationship (QSAR) of 14 phenoxybenzoic acid derivatives was studied by ab initio method at the HF/6-31G level using Guassian03 software. The optimized structures together with some characteristic and electric parameters of the title compounds were obtained; some stereo-parameters were calculated by HyperChem software. Stepwise multiple regression and principal component regression methods are adopted to establish multi-parametric models between biological activity and parameters. The results indicated that the lager Ehomo, M, V and LogP, the smaller Etumo and S, and the higher biological activity. A theoretical direction was provided to synthesize some compounds with high activity.展开更多
In order to discover the novel anti-tumor agents, a series of 2-[(pyridin-2-yl)methylthio]-1 H-benzimidazole derivatives were designed and synthesized, and the structures were characterized by IR, MS, and proton NMR...In order to discover the novel anti-tumor agents, a series of 2-[(pyridin-2-yl)methylthio]-1 H-benzimidazole derivatives were designed and synthesized, and the structures were characterized by IR, MS, and proton NMR. 2-[(3,4-Dimethoxypyridin-2-yl)methylthio]-1 Hbenzimidazole was investigated with X-ray crystallography, and the molecule is in orthorhombic system, space group P212121, with a = 9.1828(16), b = 11.625(2), c = 13.463(2) ?, Z = 4, R = 0.0231 and wR = 0.0596. The antitumor activities of target compounds were evaluated against human liver cancer cell line HepG2, and human liver normal cell line HL7702 using MTT assay. The target compounds have demonstrated weak or moderate anti-tumor activity against HepG2, while all the target compounds exhibit no cytotoxic effects on HL7702.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
The title compound C18H16N4O3 (Mr = 336.35) 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 C18H16N4O3 (Mr = 336.35) 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 central C=N double bond. It crystallizes in orthorhombic, space group P2dc with a = 7.632(1), b = 7.816(1), c = 28.082(5) A,β = 96.18(1)°, V= 1665.48(51) A^3, Z= 4, Dc = 1.341 g/cm^3, F(000) = 704,μ = 0.094 mm^-1, the final R = 0.0448 and wR = 0.1058. Of the total 3748 collections, 3105 were unique. In the molecule there exist two different planes of pyrazoline and C(11)-C(16) phenyl ring, which are approximately coplanar (r.m.s. de deviation from the combined mean plane is 0.03 A) with the dihedral angle between them of 9.8%.展开更多
The title compound,2,6-bis(2-pyridinylmethyl)-3,5-bis(2-hydroxyl-5-chlorophe nyl)-pyrazine(C26H12Cl2N4O2C2H8O2,Mr=551.41),has been synthesized and characterized by LC-ESIMS,NMR,UV and IR spectroscopy as well as ...The title compound,2,6-bis(2-pyridinylmethyl)-3,5-bis(2-hydroxyl-5-chlorophe nyl)-pyrazine(C26H12Cl2N4O2C2H8O2,Mr=551.41),has been synthesized and characterized by LC-ESIMS,NMR,UV and IR spectroscopy as well as by X-ray single-crystal diffraction.The compound behaves as a substituted pyrazine.The hydrogen atoms on C(2) and C(3) are substituted by 2-pyridinyl,whereas those on C(1) and C(4) are substituted by 2-hydroxyl-5-chlorophenyl.It crystallizes in the monoclinic system,space group P21/c with a=8.9433(12),b=32.003(4),c=10.5209(18),β=111.199(2)°,V=2807.5(7)3,Z=4,Dc=1.305 mg/m3,F(000)=1144 and μ=0.094 mm-1.A total of 13235 reflections were collected in the range of 2.17~25.01o by using a phi and omega scan mode,of which 4923 were unique(Rint=0.0692) and 2872 observed reflections with Ⅰ 〉2σ(Ⅰ) were used in the structure solution and refinement.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
A concise and efficient method for the synthesis of novel 9,10-imethoxybenzo[6,7]oxepino[3,4-b]quinolin13(6H)-one and its derivatives 7a-p has been developed via the intramolecular Friedel-Crafts acylation reactions o...A concise and efficient method for the synthesis of novel 9,10-imethoxybenzo[6,7]oxepino[3,4-b]quinolin13(6H)-one and its derivatives 7a-p has been developed via the intramolecular Friedel-Crafts acylation reactions of 6,7-dimethoxy-2-(phenoxymethyl)quinoline-3-carboxylic acids 6a-p with polyphosphoric acid (PPA) as catalyst and solvent under mild conditions. The key intermediates 6a-p were prepared through the in situ formation of ethyl 6,7-dimethoxy-2-(phenoxymethyl)quinoline-3-carboxylates 5a-p followed by hydrolysis with aqueous ethanolic sodium hydroxide solution. The novel synthetic method has the advantages of good yields, easy work-up, and environmentally friendly character, which may provide a novel highly efficient process for making quinoline and related azaheterocycle libraries.展开更多
Reaction products of 2,4,6-tris(4-phenyl-phenoxy)-1,3,5-triazine derived from 4-phenylphenol cyanate ester and phenyl glycidyl ether were analyzed. In addition to an isocyanurate compound and an oxazolidone compound w...Reaction products of 2,4,6-tris(4-phenyl-phenoxy)-1,3,5-triazine derived from 4-phenylphenol cyanate ester and phenyl glycidyl ether were analyzed. In addition to an isocyanurate compound and an oxazolidone compound which were well known as reaction products of cyanate esters and epoxy resins, compounds with hybrid ring structure of cyanurate/isocyanurate were determined. Gibbs free energies of the compound having hybrid ring structure of cyanurate/isocyanurate with two isocyanurate moiety were found to be lower than that of the compound with cyanurate ring structure through calculations. Calculation data supported the existence of hybrid ring structure of cy-anurate/isocyanurate. It was revealed that isomerization from cyanurate to isocyanurate occurs via hybrid ring structure of cyanurate/isocyanurate in the reaction of aryl cyanurate and epoxy.展开更多
Objective To study the characteristic 2-(2-phenylethyl)chromone components of endophytic fungal strain of Aquilaria sinensis by solid culture. Methods The compounds were isolated by various chromatographic methods s...Objective To study the characteristic 2-(2-phenylethyl)chromone components of endophytic fungal strain of Aquilaria sinensis by solid culture. Methods The compounds were isolated by various chromatographic methods such as silica gel, reverse-phase silica gel, Sephadex-LH20 column chromatography as well as crystallization. Results Seven 2-(2-phenylethyl)chromone analogues were isolated from the solid culture of Botryosphaeria rhodina A13. Their structures were established by spectral data as well as physicochemical properties, and identified as 6-hydroxy-7-methoxy-2-(2-phenylethyl)chromone (1), 6,7-dimethoxy-2-(2-phenylethyl) chromone (2), (5S,6R,7S,8R)-2-(2-phenylethyl)-5,6,7,8-tetrahydrchromone (3), 6- hydroxy-2-(2-phenylethyl)chromone (4), 4'-hydroxy-2-(2-phenylethyl)chromone (5), 6-methoxy-2-phenethyl-4H-chromen-4-one (6), and 6-methoxy-2-(4'-methoxy-phenethyl)-4H-chromen-4-one (7). Conclusion All of the compounds are isolated for the first time from the genus Botryosphaeria. This research opens up a new vista to produce the characteristic components of agarwood by endophytic fungi.展开更多
The behaviour of cyanothioacetamide 1 and the acetonitrile derivatives 6 and 10, respectively, towards the nitrones 2a-i induced by free solar thermal energy is reported. Structures and reaction mechanisms are also di...The behaviour of cyanothioacetamide 1 and the acetonitrile derivatives 6 and 10, respectively, towards the nitrones 2a-i induced by free solar thermal energy is reported. Structures and reaction mechanisms are also discussed.展开更多
A series of (S)-2-ethoxy-3-phenylpropanoic acid derivatives were synthesized and their insulin-sensitizing activities were evaluated in 3T3-L1 cells. Compounds 1b, 1d, 1e and 1f exhibited more potent insulin-sensiti...A series of (S)-2-ethoxy-3-phenylpropanoic acid derivatives were synthesized and their insulin-sensitizing activities were evaluated in 3T3-L1 cells. Compounds 1b, 1d, 1e and 1f exhibited more potent insulin-sensitizing activity than rosiglitazone.展开更多
A series of 2-(arylmethylidene)-2,3-dihydro-1-benzofuran-3-one derivatives(aurones, 1–20) were synthesized and screened for their inhibitory activity against h MAO. Seventeen compounds(1–5, 7–17,19) were foun...A series of 2-(arylmethylidene)-2,3-dihydro-1-benzofuran-3-one derivatives(aurones, 1–20) were synthesized and screened for their inhibitory activity against h MAO. Seventeen compounds(1–5, 7–17,19) were found to be selective towards h MAO-B, while two were non-selective(6 and 20) and one(18)selective towards h MAO-A. Compound 17(Ki = 0.10 0.01 mmol/L) was found to be equally potent and selective towards h MAO-B, when compared with the standard drug Selegiline(Ki = 0.12 0.01 mmol/L).Nature and position of substitution in aryl ring at 2nd position of benzofuranone influences h MAO-B inhibitory potency, while their structural bulkiness influences selectivity between h MAO-A and h MAO-B.Molecular docking simulation was also carried out to understand the interaction of inhibitor with the enzyme at molecular level, and we found the docking results were in good agreement with the experimental values. Comparison of the activity profile of the aurones with their corresponding flavones reported earlier by our group revealed that there exists no difference in potency as well as selectivity.展开更多
文摘One novel spirolactone,aquilarisinolide(1),three new sesquiterpenoids,(2R,4S,5R,7R)-2-hydroxyeremophila-9,11-dien-8-one(2),(1R,4S,5S,7R,11R)-13-hydroxyepidaphnauran-9-en-8-one(3),and(4R,5S,7R,8S,10S,13R)-8,13-dihydroxyrotunda-1,11-dien-3-one(4),together with 13 known compounds(5-17)were isolated from the resinous heartwood of Aquilaria sinensis(Thymelaeaceae).The structures of the new compounds were elucidated based on the analysis of NMR and MS data and theoretical calculations their ECD spectra.The isolated compounds were evaluated for their protective activities against PC12 cell injury induced by corticosterone(CORT)and 1-methyl-4-phenylpyridine ion(MPP+),as well as inhibitory activities against BACE1.Compound 4,5,6-dihydroxy-2-(2-phenylethyl)chromone(5),daphnauranol B(7),6-methoxy-2-[2-(3-methyoxyphenyl)ethyl]chromone(10),isoagarotetrol(14),and 1-hydroxy-1,5-diphenylpentan-3-one(16)showed significant protective effects on CORT-induced injury in PC12 cells at a concentration of 20μM(P<0.001).Isoagarotetrol(14)showed a significant protective effect on MPP+-induced injury in PC12 cells at a concentration of 20μM(P<0.001),while compound 4 showed a moderate activity(P<0.01).The BACE1-inhibitory activities of all tested compounds were very weak with less than 30%inhibition at a concentration of 20μM.
基金supported by Beijing Sino-Science Aquilaria Technology Co.,Ltd.,Beijing,China (no.KET202101).
文摘Five new 2-(2-phenylethyl)chromone derivatives,(5S,6R,7R,8S,7ʹR)-7ʹ-hydroxyagarotetrol(1),(5S,6R,7R,8S,7ʹS)-7ʹ-hydroxyagarotetrol(2),(6S,7S,8R)-2-[2-(4-methoxyphenyl)ethyl]-6,7,8-trihydroxy-5,6,7,8-tetrahydrochromone(3),(6S,7S,8R)-2-(2-phenylethyl)-6,7,8-trihydroxy-5,6,7,8-tetrahydrochromone(4),(5S,6R,7S,8R)-2-(2-phenylethyl)-5,6,7-trihydroxy-5,6,7,8-tetrahydro-8-[2-(2-phenylethyl)-7-methoxychromonyl-6-oxy]chromone(5),three new sesquiterpenoids,(4S,5S,7S,8S,10S,13R)-7,8,13-trihydroxyrotunda-1,11-dien-3-one(6),(4S,5S,7S,8S,10S,13S)-7,8,13-trihydroxyrotunda-1,11-dien-3-one(7),and(4R,5S,7S,8S,10S,13S)-7,8,13-trihydroxyrotunda-1,11-dien-3-one(8),along with 14 known compounds were isolated from the resinous heartwood of Aquilaria sinensis(Thymelaeaceae).The chemical structures of these new compounds were elucidated by 1D and 2D NMR and MS data,single-crystal X-ray diffraction analysis,and electronic circular dichroism(ECD)calculations.The neuroprotective activities of these isolates were evaluated using an in vitro model of rat adrenal pheochromocytoma(PC12)cell injury induced by corticosterone.At concentrations from 5 to 40μM,compounds 4 and 6,agarotetrol(9),and 6-hydroxy-2-(2-phenylethyl)chromone(17)showed significant protective activities against corticosterone-induced PC12 cell injury(P<0.001).
文摘5-Hydroxy-2-(2-phenylethyl)chromone(l) was synthesized from 2,6-dihydroxyacetophenone(7) obtained via four-steps resorcinol-reacting with phenylpropionic acid, the procedures involved are Baker-Venkataraman rear-rangement and cyclization which are easy to conduct, the overall yield is 32%.
文摘Nine 3,3’-(arylmethylene)bis(2-hydroxynaphthalene-1,4-dione) derivatives were synthesized through the reaction between 2-hydroxy-1,4-naphthalen-1,4-dione and different aromatic alde-hydes in water applying ultrasonic irradiation for 5 min at room temperature and microwave irradiation for 15 min at 70°;C. Two of the nine derivatives, compounds 3-e and 3-i, obtained from 3-bromo-hydroxybenzaldehyde and 5-methylfuran-2-carbaldehyde, respectively, are previously unpublished. The structures of all compounds were established on the basis of their spectral data and mass analysis. The attractive features of this synthesis protocol include mild conditions, high atom-economy and excellent yields with the elimination of water as the only by-product.
基金This work was supported by the Natural Science Foundation of Fujian Province (X0650070)
文摘The quantitative structure-activity relationship (QSAR) of 14 phenoxybenzoic acid derivatives was studied by ab initio method at the HF/6-31G level using Guassian03 software. The optimized structures together with some characteristic and electric parameters of the title compounds were obtained; some stereo-parameters were calculated by HyperChem software. Stepwise multiple regression and principal component regression methods are adopted to establish multi-parametric models between biological activity and parameters. The results indicated that the lager Ehomo, M, V and LogP, the smaller Etumo and S, and the higher biological activity. A theoretical direction was provided to synthesize some compounds with high activity.
基金supported by the National Natural Science Foundation of China(No.21342006)the Program for Innovative Research Team of the Ministry of Education of China(No.IRT_14R36)
文摘In order to discover the novel anti-tumor agents, a series of 2-[(pyridin-2-yl)methylthio]-1 H-benzimidazole derivatives were designed and synthesized, and the structures were characterized by IR, MS, and proton NMR. 2-[(3,4-Dimethoxypyridin-2-yl)methylthio]-1 Hbenzimidazole was investigated with X-ray crystallography, and the molecule is in orthorhombic system, space group P212121, with a = 9.1828(16), b = 11.625(2), c = 13.463(2) ?, Z = 4, R = 0.0231 and wR = 0.0596. The antitumor activities of target compounds were evaluated against human liver cancer cell line HepG2, and human liver normal cell line HL7702 using MTT assay. The target compounds have demonstrated weak or moderate anti-tumor activity against HepG2, while all the target compounds exhibit no cytotoxic effects on HL7702.
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The title compound C18H16N4O3 (Mr = 336.35) 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 central C=N double bond. It crystallizes in orthorhombic, space group P2dc with a = 7.632(1), b = 7.816(1), c = 28.082(5) A,β = 96.18(1)°, V= 1665.48(51) A^3, Z= 4, Dc = 1.341 g/cm^3, F(000) = 704,μ = 0.094 mm^-1, the final R = 0.0448 and wR = 0.1058. Of the total 3748 collections, 3105 were unique. In the molecule there exist two different planes of pyrazoline and C(11)-C(16) phenyl ring, which are approximately coplanar (r.m.s. de deviation from the combined mean plane is 0.03 A) with the dihedral angle between them of 9.8%.
基金supported by the research grant of Phytochemistry Key Laboratory of Shaanxi Province (No. 02js40)
文摘The title compound,2,6-bis(2-pyridinylmethyl)-3,5-bis(2-hydroxyl-5-chlorophe nyl)-pyrazine(C26H12Cl2N4O2C2H8O2,Mr=551.41),has been synthesized and characterized by LC-ESIMS,NMR,UV and IR spectroscopy as well as by X-ray single-crystal diffraction.The compound behaves as a substituted pyrazine.The hydrogen atoms on C(2) and C(3) are substituted by 2-pyridinyl,whereas those on C(1) and C(4) are substituted by 2-hydroxyl-5-chlorophenyl.It crystallizes in the monoclinic system,space group P21/c with a=8.9433(12),b=32.003(4),c=10.5209(18),β=111.199(2)°,V=2807.5(7)3,Z=4,Dc=1.305 mg/m3,F(000)=1144 and μ=0.094 mm-1.A total of 13235 reflections were collected in the range of 2.17~25.01o by using a phi and omega scan mode,of which 4923 were unique(Rint=0.0692) and 2872 observed reflections with Ⅰ 〉2σ(Ⅰ) were used in the structure solution and refinement.
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°.
文摘A concise and efficient method for the synthesis of novel 9,10-imethoxybenzo[6,7]oxepino[3,4-b]quinolin13(6H)-one and its derivatives 7a-p has been developed via the intramolecular Friedel-Crafts acylation reactions of 6,7-dimethoxy-2-(phenoxymethyl)quinoline-3-carboxylic acids 6a-p with polyphosphoric acid (PPA) as catalyst and solvent under mild conditions. The key intermediates 6a-p were prepared through the in situ formation of ethyl 6,7-dimethoxy-2-(phenoxymethyl)quinoline-3-carboxylates 5a-p followed by hydrolysis with aqueous ethanolic sodium hydroxide solution. The novel synthetic method has the advantages of good yields, easy work-up, and environmentally friendly character, which may provide a novel highly efficient process for making quinoline and related azaheterocycle libraries.
文摘Reaction products of 2,4,6-tris(4-phenyl-phenoxy)-1,3,5-triazine derived from 4-phenylphenol cyanate ester and phenyl glycidyl ether were analyzed. In addition to an isocyanurate compound and an oxazolidone compound which were well known as reaction products of cyanate esters and epoxy resins, compounds with hybrid ring structure of cyanurate/isocyanurate were determined. Gibbs free energies of the compound having hybrid ring structure of cyanurate/isocyanurate with two isocyanurate moiety were found to be lower than that of the compound with cyanurate ring structure through calculations. Calculation data supported the existence of hybrid ring structure of cy-anurate/isocyanurate. It was revealed that isomerization from cyanurate to isocyanurate occurs via hybrid ring structure of cyanurate/isocyanurate in the reaction of aryl cyanurate and epoxy.
基金National Basic Research Program of China(973 Program,2014CB460613)National Natural Science Foundation of China(81203006)+2 种基金Natural Science Foundation of Guangdong Province(2015A030313710)Guangdong Provincial Project for Science and Technology(2014A030304050,2015A030302060)Observation Station Foundation of Guangdong Academy of Science(Sytz201504,Sytz201511)
文摘Objective To study the characteristic 2-(2-phenylethyl)chromone components of endophytic fungal strain of Aquilaria sinensis by solid culture. Methods The compounds were isolated by various chromatographic methods such as silica gel, reverse-phase silica gel, Sephadex-LH20 column chromatography as well as crystallization. Results Seven 2-(2-phenylethyl)chromone analogues were isolated from the solid culture of Botryosphaeria rhodina A13. Their structures were established by spectral data as well as physicochemical properties, and identified as 6-hydroxy-7-methoxy-2-(2-phenylethyl)chromone (1), 6,7-dimethoxy-2-(2-phenylethyl) chromone (2), (5S,6R,7S,8R)-2-(2-phenylethyl)-5,6,7,8-tetrahydrchromone (3), 6- hydroxy-2-(2-phenylethyl)chromone (4), 4'-hydroxy-2-(2-phenylethyl)chromone (5), 6-methoxy-2-phenethyl-4H-chromen-4-one (6), and 6-methoxy-2-(4'-methoxy-phenethyl)-4H-chromen-4-one (7). Conclusion All of the compounds are isolated for the first time from the genus Botryosphaeria. This research opens up a new vista to produce the characteristic components of agarwood by endophytic fungi.
文摘The behaviour of cyanothioacetamide 1 and the acetonitrile derivatives 6 and 10, respectively, towards the nitrones 2a-i induced by free solar thermal energy is reported. Structures and reaction mechanisms are also discussed.
基金Project supported by the National Natural Science Foundation of China (No. 30500390) and the Science Foundation of the Hunan Education Department (No. 06B075).
文摘A series of (S)-2-ethoxy-3-phenylpropanoic acid derivatives were synthesized and their insulin-sensitizing activities were evaluated in 3T3-L1 cells. Compounds 1b, 1d, 1e and 1f exhibited more potent insulin-sensitizing activity than rosiglitazone.
基金Birla Institute of Technology for providing financial support as a prestigious Institute fellowship
文摘A series of 2-(arylmethylidene)-2,3-dihydro-1-benzofuran-3-one derivatives(aurones, 1–20) were synthesized and screened for their inhibitory activity against h MAO. Seventeen compounds(1–5, 7–17,19) were found to be selective towards h MAO-B, while two were non-selective(6 and 20) and one(18)selective towards h MAO-A. Compound 17(Ki = 0.10 0.01 mmol/L) was found to be equally potent and selective towards h MAO-B, when compared with the standard drug Selegiline(Ki = 0.12 0.01 mmol/L).Nature and position of substitution in aryl ring at 2nd position of benzofuranone influences h MAO-B inhibitory potency, while their structural bulkiness influences selectivity between h MAO-A and h MAO-B.Molecular docking simulation was also carried out to understand the interaction of inhibitor with the enzyme at molecular level, and we found the docking results were in good agreement with the experimental values. Comparison of the activity profile of the aurones with their corresponding flavones reported earlier by our group revealed that there exists no difference in potency as well as selectivity.