A series of 8,9-dihydro-2-（2-oxo-2H-chromen-3-yl）-5-aryl-3H-chromeno[2,3-d]pyrimidine-4,6（5H^7H）-diones （Sa-j）have been synthesized by the reaction of 2-amino-5,6,7,8-tetrahydro-5-oxo-4-aryl-4H-chromene-3-carbon...A series of 8,9-dihydro-2-（2-oxo-2H-chromen-3-yl）-5-aryl-3H-chromeno[2,3-d]pyrimidine-4,6（5H^7H）-diones （Sa-j）have been synthesized by the reaction of 2-amino-5,6,7,8-tetrahydro-5-oxo-4-aryl-4H-chromene-3-carbonitrile （4a-j） with couma- rin-3-catboxylic acid under neat conditions employing Brnsted acidic ionic liquid （4-sulfobutyl）tris（4-sulfophenyl）phosphonium hydrogen sulfate as catalyst. Structures of all the compounds were established on the basis of analytical and spectroscopic data. All the compounds were evaluated for their in vitro antimicrobial activity against different bacterial and fungal strains.展开更多
Based on the principles of the bioisosterism, combination of the active substructures of selective estrogen receptor modulators which are currently therapeutic agents available for the prevention and treatment of vari...Based on the principles of the bioisosterism, combination of the active substructures of selective estrogen receptor modulators which are currently therapeutic agents available for the prevention and treatment of various estrogen dependent diseases, and structural optimization, a novel series of 2-aroyl-3-aryl-6,7-dihydro-5H-furo[3,2-g]- chromen derivatives was designed as potent selective estrogen receptor modulators via molecular docking. The target compounds have been synthesized, and characterized by 1R, proton NMR, ESI-MS, elemental analysis and evaluated for their antitumor activity against human osteosarcoma U2OS-EGFP-4FI2G cell line. Some target compounds showed good inhibition effects on U2OS-EGFP-4F12G cell line and the preliminary structure-activity relationships were discussed.展开更多
The esterifications of 9-（hydroxyimino）-4-methyl-8,9-dihydrofuro[2,3-h]chromen-2-one （4） with acid chlorides afforded normal oxime-esters 3a-e in 35-78% yields in presence of excessive 4-dimethylaminopyridine as t...The esterifications of 9-（hydroxyimino）-4-methyl-8,9-dihydrofuro[2,3-h]chromen-2-one （4） with acid chlorides afforded normal oxime-esters 3a-e in 35-78% yields in presence of excessive 4-dimethylaminopyridine as the acid scavenger, whereas the reactions gave unexpected 8-substituted products N-（8-chloro-4-methyl-2-oxo-2H-furo-[2,3-h]chromen-9-yl）amides （5a-c） and 4-methyl-2,9-dioxo-8,9-dihydro-2H-furo[2,3-h]chromen-8-ylcarboxyloates （6d-e） by using excessive acid chlorides. The structures of 10 new compounds were determined by 1H NMR, 13C NMR, MS and HRMS, and the possible mechanism for the formation of unexpected products 5a--c and 6d-e was also proposed.展开更多
The crystal structure of the title compound （C22H17BrOs, Mr = 441.27） has been determined by single-crystal X-ray diffraction. The crystal is of orthorhombic system, space group Pna21 with a = 11.76（I）, b = 14.58...The crystal structure of the title compound （C22H17BrOs, Mr = 441.27） has been determined by single-crystal X-ray diffraction. The crystal is of orthorhombic system, space group Pna21 with a = 11.76（I）, b = 14.58（1）, c = 11.52（1）A, V= 1973.9A3, Z= 4, Dc = 1.485 g/cm3, F（000） = 896,μ（MoKa） = 2.113 mm-1, the final R = 0.0394 and wR = 0.0809 for 3918 observed reflections （1 〉 2o（/））. The single-crystal X-ray diffraction data indicate that the C=C bond is in an E-configuration. The intramolecular C（10）-H（10B）...O（4） and intermolecular C（17）-H（I 7）...0（4） hydrogen bonds contribute to the stability of the structure.展开更多
A new series of 1-ethoxy-3-（4-aryl）-1-phenyl-1H-benzo[f]chromenes have been synthesized efficiently.The procedure involves the multicomponent reaction of 2-naphthol,acetophenone derivatives,and triethyl orthobenzoat...A new series of 1-ethoxy-3-（4-aryl）-1-phenyl-1H-benzo[f]chromenes have been synthesized efficiently.The procedure involves the multicomponent reaction of 2-naphthol,acetophenone derivatives,and triethyl orthobenzoate catalyzing by efficient bis（2-anilinotropone） Ti complex.展开更多
The crystal structure of the potential active N-[2-(6-Methoxy-2-oxo-2H-chromen-4-yl)-benzofuran-3-yl]-benzamide (C25H17NO5) (I) has been determined from single crystal X-ray diffraction data. The title compound crysta...The crystal structure of the potential active N-[2-(6-Methoxy-2-oxo-2H-chromen-4-yl)-benzofuran-3-yl]-benzamide (C25H17NO5) (I) has been determined from single crystal X-ray diffraction data. The title compound crystallizes in the monoclinic space group P 21/n, with a = 12.0551(11), b = 9.7853(8), c = 16.6517(16) , β = 90.092(4)o, V = 1964.28(3) 3, Dcalc = 1.391 Mg/m3, Z = 4. In the structure, intermolecular H-bonds lead to the formation of a centrosymmetric dimer of the molecule. There is an intramolecular C7—H7…N1 hydrogen bond forming a closed seven membered ring. There are also intramolecular π-π interactions presented between the 3,6-Dihydro-2H-pyran ring of the chromen moiety [Cg2…Cg2 distance = 3.5812(13) ]. The packing structure is stabilized by these C—H…N, N—H…O hydrogen bonds, C—H… π and π…π interactions.展开更多
Application of the Suzuki cross-coupling reaction for efficient synthesis of diverse substituted biaryl-chromen- 4-ones using an optimized palladium（0） catalyst system is reported. The coupling of arylboronic acids ...Application of the Suzuki cross-coupling reaction for efficient synthesis of diverse substituted biaryl-chromen- 4-ones using an optimized palladium（0） catalyst system is reported. The coupling of arylboronic acids with the resin-bound bromoflavanones which were prepared by organoselenium-induced regioselective intramolecular cy- clization of bromo-2-hydroxylchalcones proceeded smoothly. Biaryl-chromen-4-ones were synthesized by subse- quent selenoxide syn-elimination in good total yields.展开更多
Photocyclisation of substituted （E）-3-hydroxy-2-（V-methyl-2＇-phenylvinyl）-4-oxo-4H-1-benzopyrans to yield linear novel tricyclic 9H-furo[3,2-b]chromen-9-ones and angular fused tetracyclic xanthenones is described.
A new europium(Ⅲ)complex containing(4-Methyl-2-oxo-2 H-chromen-7-yloxy)-acetic acid moiety(CMMC)was synthesized,characterized,and confirmed as antitumor agent and fluorescent probe.The spectroscopic measurements of ...A new europium(Ⅲ)complex containing(4-Methyl-2-oxo-2 H-chromen-7-yloxy)-acetic acid moiety(CMMC)was synthesized,characterized,and confirmed as antitumor agent and fluorescent probe.The spectroscopic measurements of Eu(Ⅲ)in the presence of CMMC were obtained in different solvents.The results show that the strongest Eu(Ⅲ)emission bands were monitored in iso-propyl alcohol while the weakest Eu(Ⅲ)emission band was observed in acetonitrile.The interaction of Eu(Ⅲ)-(CMMC)2 complex with DNA was monitored using absorption and emission techniques.From fluorescence titration measurements,the binding constants of DNA with Eu(Ⅲ)-(CMMC)_2 complex were found to be 1.04×10~5 L·mol^(-1) in Tris-HCl and 1.17×10~7 L·mol^(-1) in DMSO-Tris-HCl buffer(9∶1 V/V).Hypochromism was observed from the absorption titration experiment which indicates the intercalation of Eu(Ⅲ)-complex between the base pair of DNA.This result further confirmed by fluorescent Ethidium bromide displacement assay.The fluorescence calibration curve was used for the determination of DNA with LOD of 1.2 ng in DMSO-Tris-HCl buffer(9∶1 V/V)and 5 ng in Tris-HCl buffer.The preliminary antitumor investigation shows promising cytotoxicity against MDA-MB-231,MCF-7(mammary cancer),and PC-3(prostate carcinoma)cell lines with IC50 values of 40.63,25.42 and 30.25μmol·L^(-1),respectively.展开更多
A new series of compounds, 1-aryl-3-（3,4-dihydro-2H-chromen-5-yl） ureas, have been synthesized and their structures were confirmed by FAB-MS and IH NMR. The preliminary pharmacological screening showed that these co...A new series of compounds, 1-aryl-3-（3,4-dihydro-2H-chromen-5-yl） ureas, have been synthesized and their structures were confirmed by FAB-MS and IH NMR. The preliminary pharmacological screening showed that these compounds inhibited TNF-α production in lipopolysaccharide （LPS）-stimulated THP-1 cells.展开更多
To study the intramolecular Diels-Alder cycloadditon of 2H-chromen-2-one as a diene, a series of chiral N-allyl-N-benzylamides that contain a 2H-chrornen-2-one moiety were designed for the synthesis of benzo[f]isoindo...To study the intramolecular Diels-Alder cycloadditon of 2H-chromen-2-one as a diene, a series of chiral N-allyl-N-benzylamides that contain a 2H-chrornen-2-one moiety were designed for the synthesis of benzo[f]isoindol-1-ones via an intrarnolecular Diels-Alder and a subsequent retro-Diels-Alder cycloaddition with the expulsion of CO2. Both the yield （80%-89%） and absolute stereocontrol of the tandem reaction were high when an electron-withdrawing group was attached to the dienophile. The double bond in the styrene substructure remained in the products could be further derivatized by dihydroxylation.展开更多
文摘A series of 8,9-dihydro-2-（2-oxo-2H-chromen-3-yl）-5-aryl-3H-chromeno[2,3-d]pyrimidine-4,6（5H^7H）-diones （Sa-j）have been synthesized by the reaction of 2-amino-5,6,7,8-tetrahydro-5-oxo-4-aryl-4H-chromene-3-carbonitrile （4a-j） with couma- rin-3-catboxylic acid under neat conditions employing Brnsted acidic ionic liquid （4-sulfobutyl）tris（4-sulfophenyl）phosphonium hydrogen sulfate as catalyst. Structures of all the compounds were established on the basis of analytical and spectroscopic data. All the compounds were evaluated for their in vitro antimicrobial activity against different bacterial and fungal strains.
基金Supported by the National Natural Science Foundation of China(No20474053)
文摘Based on the principles of the bioisosterism, combination of the active substructures of selective estrogen receptor modulators which are currently therapeutic agents available for the prevention and treatment of various estrogen dependent diseases, and structural optimization, a novel series of 2-aroyl-3-aryl-6,7-dihydro-5H-furo[3,2-g]- chromen derivatives was designed as potent selective estrogen receptor modulators via molecular docking. The target compounds have been synthesized, and characterized by 1R, proton NMR, ESI-MS, elemental analysis and evaluated for their antitumor activity against human osteosarcoma U2OS-EGFP-4FI2G cell line. Some target compounds showed good inhibition effects on U2OS-EGFP-4F12G cell line and the preliminary structure-activity relationships were discussed.
基金grants from the National Natural Science Foundation of China (No.20272010 and 20672022)
文摘The esterifications of 9-（hydroxyimino）-4-methyl-8,9-dihydrofuro[2,3-h]chromen-2-one （4） with acid chlorides afforded normal oxime-esters 3a-e in 35-78% yields in presence of excessive 4-dimethylaminopyridine as the acid scavenger, whereas the reactions gave unexpected 8-substituted products N-（8-chloro-4-methyl-2-oxo-2H-furo-[2,3-h]chromen-9-yl）amides （5a-c） and 4-methyl-2,9-dioxo-8,9-dihydro-2H-furo[2,3-h]chromen-8-ylcarboxyloates （6d-e） by using excessive acid chlorides. The structures of 10 new compounds were determined by 1H NMR, 13C NMR, MS and HRMS, and the possible mechanism for the formation of unexpected products 5a--c and 6d-e was also proposed.
基金Supported by NNSFC(No.20872046)the Fundamental Research Funds for the Central Universities(No.CCNU09A02013)
文摘The crystal structure of the title compound （C22H17BrOs, Mr = 441.27） has been determined by single-crystal X-ray diffraction. The crystal is of orthorhombic system, space group Pna21 with a = 11.76（I）, b = 14.58（1）, c = 11.52（1）A, V= 1973.9A3, Z= 4, Dc = 1.485 g/cm3, F（000） = 896,μ（MoKa） = 2.113 mm-1, the final R = 0.0394 and wR = 0.0809 for 3918 observed reflections （1 〉 2o（/））. The single-crystal X-ray diffraction data indicate that the C=C bond is in an E-configuration. The intramolecular C（10）-H（10B）...O（4） and intermolecular C（17）-H（I 7）...0（4） hydrogen bonds contribute to the stability of the structure.
文摘A new series of 1-ethoxy-3-（4-aryl）-1-phenyl-1H-benzo[f]chromenes have been synthesized efficiently.The procedure involves the multicomponent reaction of 2-naphthol,acetophenone derivatives,and triethyl orthobenzoate catalyzing by efficient bis（2-anilinotropone） Ti complex.
文摘The crystal structure of the potential active N-[2-(6-Methoxy-2-oxo-2H-chromen-4-yl)-benzofuran-3-yl]-benzamide (C25H17NO5) (I) has been determined from single crystal X-ray diffraction data. The title compound crystallizes in the monoclinic space group P 21/n, with a = 12.0551(11), b = 9.7853(8), c = 16.6517(16) , β = 90.092(4)o, V = 1964.28(3) 3, Dcalc = 1.391 Mg/m3, Z = 4. In the structure, intermolecular H-bonds lead to the formation of a centrosymmetric dimer of the molecule. There is an intramolecular C7—H7…N1 hydrogen bond forming a closed seven membered ring. There are also intramolecular π-π interactions presented between the 3,6-Dihydro-2H-pyran ring of the chromen moiety [Cg2…Cg2 distance = 3.5812(13) ]. The packing structure is stabilized by these C—H…N, N—H…O hydrogen bonds, C—H… π and π…π interactions.
文摘Application of the Suzuki cross-coupling reaction for efficient synthesis of diverse substituted biaryl-chromen- 4-ones using an optimized palladium（0） catalyst system is reported. The coupling of arylboronic acids with the resin-bound bromoflavanones which were prepared by organoselenium-induced regioselective intramolecular cy- clization of bromo-2-hydroxylchalcones proceeded smoothly. Biaryl-chromen-4-ones were synthesized by subse- quent selenoxide syn-elimination in good total yields.
文摘Photocyclisation of substituted （E）-3-hydroxy-2-（V-methyl-2＇-phenylvinyl）-4-oxo-4H-1-benzopyrans to yield linear novel tricyclic 9H-furo[3,2-b]chromen-9-ones and angular fused tetracyclic xanthenones is described.
基金supported by grants 4590/1434 by Deanship of Scientific Resea rch at Taibah University in Saudi Arabia for financial assistance
文摘A new europium(Ⅲ)complex containing(4-Methyl-2-oxo-2 H-chromen-7-yloxy)-acetic acid moiety(CMMC)was synthesized,characterized,and confirmed as antitumor agent and fluorescent probe.The spectroscopic measurements of Eu(Ⅲ)in the presence of CMMC were obtained in different solvents.The results show that the strongest Eu(Ⅲ)emission bands were monitored in iso-propyl alcohol while the weakest Eu(Ⅲ)emission band was observed in acetonitrile.The interaction of Eu(Ⅲ)-(CMMC)2 complex with DNA was monitored using absorption and emission techniques.From fluorescence titration measurements,the binding constants of DNA with Eu(Ⅲ)-(CMMC)_2 complex were found to be 1.04×10~5 L·mol^(-1) in Tris-HCl and 1.17×10~7 L·mol^(-1) in DMSO-Tris-HCl buffer(9∶1 V/V).Hypochromism was observed from the absorption titration experiment which indicates the intercalation of Eu(Ⅲ)-complex between the base pair of DNA.This result further confirmed by fluorescent Ethidium bromide displacement assay.The fluorescence calibration curve was used for the determination of DNA with LOD of 1.2 ng in DMSO-Tris-HCl buffer(9∶1 V/V)and 5 ng in Tris-HCl buffer.The preliminary antitumor investigation shows promising cytotoxicity against MDA-MB-231,MCF-7(mammary cancer),and PC-3(prostate carcinoma)cell lines with IC50 values of 40.63,25.42 and 30.25μmol·L^(-1),respectively.
文摘A new series of compounds, 1-aryl-3-（3,4-dihydro-2H-chromen-5-yl） ureas, have been synthesized and their structures were confirmed by FAB-MS and IH NMR. The preliminary pharmacological screening showed that these compounds inhibited TNF-α production in lipopolysaccharide （LPS）-stimulated THP-1 cells.
基金supported by the research grant from the National Natural Science Foundation of China (No. 21172191)
文摘To study the intramolecular Diels-Alder cycloadditon of 2H-chromen-2-one as a diene, a series of chiral N-allyl-N-benzylamides that contain a 2H-chrornen-2-one moiety were designed for the synthesis of benzo[f]isoindol-1-ones via an intrarnolecular Diels-Alder and a subsequent retro-Diels-Alder cycloaddition with the expulsion of CO2. Both the yield （80%-89%） and absolute stereocontrol of the tandem reaction were high when an electron-withdrawing group was attached to the dienophile. The double bond in the styrene substructure remained in the products could be further derivatized by dihydroxylation.
