A series of novel 2-trifluoromethylthieno[2,3-d]pyrimidine derivatives were synthesized by a facile three-step procedure that afforded advantages of mild reaction conditions, simple protocol and good yields. The struc...A series of novel 2-trifluoromethylthieno[2,3-d]pyrimidine derivatives were synthesized by a facile three-step procedure that afforded advantages of mild reaction conditions, simple protocol and good yields. The structures of the final compounds were confirmed by 1R, NMR, El-MS, elemental analysis, and X-ray diffraction. Preliminary bioassay results showed that some of the analogs exhibit excellent antitumor activity against MCF-7 and HepG2, especially compounds 3a, 3b, 3e and 3h exhibited higher activity than the positive control gefitinib.展开更多
Two series of thieno[2,3-d]pyrimidine derivatives were designed and synthesized, in which bioactive α-aminophosphonate subunits were introduced at the N3 position through an N-N bond connection. The in vitro cytotoxi...Two series of thieno[2,3-d]pyrimidine derivatives were designed and synthesized, in which bioactive α-aminophosphonate subunits were introduced at the N3 position through an N-N bond connection. The in vitro cytotoxic activity of the novel compounds was tested against human esophageal carcinoma cells （EC109）, human hepatocarcinoma cells （HepG2）, human gastric carcinoma cells （MGC-803）, respectively, by the MTT method. The evaluation results revealed that compounds fimb, 6mf, 6mg, 6rid and 6nh exerted the most potent inhibition against HepG2, MGC-803 and EC109 cells, respectively. In particular, compound 6rag presented excellent inhibitory effect against HepG2 （91.2%） and MGC-803 （94.4%） cells.展开更多
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
The novel title compound 4-chlorobenzaldehyde （2-trifluoromethyl-5,6,7,8- tetrahydro- benzo[4,5]thieno[2,3-d]pyrimidin-4-yl）hydrazone monohydrate （C18H14C1F3N4S.H20, Mr = 428.86） has been synthesized by a condensa...The novel title compound 4-chlorobenzaldehyde （2-trifluoromethyl-5,6,7,8- tetrahydro- benzo[4,5]thieno[2,3-d]pyrimidin-4-yl）hydrazone monohydrate （C18H14C1F3N4S.H20, Mr = 428.86） has been synthesized by a condensation reaction of 4-chlorobenzaldehyde with （2-trifuoromethyl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-yl）hydrazine, and its crystal structure was determined by single-crystal X-ray diffraction. The crystal belongs to monoclinic, space group P21/c with a = 7.4252（7）, b = 26.344（2）, c = 10.3095（9） A, /3 = 109.407（2）~, V= 1902.0（3） A3, Z = 4, Dc = 1.498 g/cm^3, p = 0.356 mm-1, F（000） = 880, the final R = 0.0564 and wR = 0.1681 for 2343 observed reflections with I 〉 2o（/）. X-ray diffraction analysis reveals that the title hydrazone molecule is nearly planar except for the cyclohexene and trifluoromethyl moieties. In the crystal packing, the molecules form stacks by a three-dimensional framework, which results from intermolecular N（3）-H（3）...O（1）, O（1）-H（1B）...N（2）, O（1）- H（1B）...N（4） and O（1）-H（1A）...F（1） hydrogen bonds via water molecules together with π-π stacking interactions. Molecular geometry of the title compound in the ground state optimized by B3LYP functional with 6-311G＊＊ basis sets indicates that the calculations are in agreement with the experimental data. The preliminary bioassay suggested that the title compound exhibits relatively good fungicidal activity against Fusarium oxysporium fsp.vasinfectum and Dothiorella gregaria.展开更多
The title compound, 3-[2-（4-fluoro-phenyl）-ethyl]-5-methyl-4-hydroxyl-4-methyl- 7-methylsulfanyl-3,4-dihydro-pyrido[4,3-d]pyrimidine-8-carbonitrile, has been prepared and detemined by single-crystal X-ray diffractio...The title compound, 3-[2-（4-fluoro-phenyl）-ethyl]-5-methyl-4-hydroxyl-4-methyl- 7-methylsulfanyl-3,4-dihydro-pyrido[4,3-d]pyrimidine-8-carbonitrile, has been prepared and detemined by single-crystal X-ray diffraction. The crystal belongs to the triclinic system, space group P1 with a = 6.8754（8）, b = 10.2617（12）, c = 13.3491（16） A, α = 93.163（2）, β = 96.704（2）, γ = 102.421（2）°, V= 910.35（19）A^3, Z= 2, Mr= 370.44, Dc= 1.351 g/cm^3,μ = 0.203 mm^-1,F（000） = 388, the final R = 0.0573 and wR = 0.1497. X-ray analysis reveals that the pyridine and pyrimidine rings are almost coplanar.展开更多
基金financially supported by the National Natural Science Foundation of China(No.21262012)the Open Fund of Key Laboratory of Biologic Resources Protection and Utilization of Hubei Province(No.PKLHB1314)
文摘A series of novel 2-trifluoromethylthieno[2,3-d]pyrimidine derivatives were synthesized by a facile three-step procedure that afforded advantages of mild reaction conditions, simple protocol and good yields. The structures of the final compounds were confirmed by 1R, NMR, El-MS, elemental analysis, and X-ray diffraction. Preliminary bioassay results showed that some of the analogs exhibit excellent antitumor activity against MCF-7 and HepG2, especially compounds 3a, 3b, 3e and 3h exhibited higher activity than the positive control gefitinib.
基金supported by the National Natural Sciences Foundations of China (Nos.21171149,21105091)
文摘Two series of thieno[2,3-d]pyrimidine derivatives were designed and synthesized, in which bioactive α-aminophosphonate subunits were introduced at the N3 position through an N-N bond connection. The in vitro cytotoxic activity of the novel compounds was tested against human esophageal carcinoma cells （EC109）, human hepatocarcinoma cells （HepG2）, human gastric carcinoma cells （MGC-803）, respectively, by the MTT method. The evaluation results revealed that compounds fimb, 6mf, 6mg, 6rid and 6nh exerted the most potent inhibition against HepG2, MGC-803 and EC109 cells, respectively. In particular, compound 6rag presented excellent inhibitory effect against HepG2 （91.2%） and MGC-803 （94.4%） cells.
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 (No.21262012)the Natural Science Foundation of Hubei Province (No.2011CDB087)+1 种基金the Scientific Research Fund of Hubei Provincial Education Department (No.Q20122909)the Project of Team Research for Excellent Mid-Aged & Young Teachers of Higher Education of Hubei Province, China (No.T201006)
文摘The novel title compound 4-chlorobenzaldehyde （2-trifluoromethyl-5,6,7,8- tetrahydro- benzo[4,5]thieno[2,3-d]pyrimidin-4-yl）hydrazone monohydrate （C18H14C1F3N4S.H20, Mr = 428.86） has been synthesized by a condensation reaction of 4-chlorobenzaldehyde with （2-trifuoromethyl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-yl）hydrazine, and its crystal structure was determined by single-crystal X-ray diffraction. The crystal belongs to monoclinic, space group P21/c with a = 7.4252（7）, b = 26.344（2）, c = 10.3095（9） A, /3 = 109.407（2）~, V= 1902.0（3） A3, Z = 4, Dc = 1.498 g/cm^3, p = 0.356 mm-1, F（000） = 880, the final R = 0.0564 and wR = 0.1681 for 2343 observed reflections with I 〉 2o（/）. X-ray diffraction analysis reveals that the title hydrazone molecule is nearly planar except for the cyclohexene and trifluoromethyl moieties. In the crystal packing, the molecules form stacks by a three-dimensional framework, which results from intermolecular N（3）-H（3）...O（1）, O（1）-H（1B）...N（2）, O（1）- H（1B）...N（4） and O（1）-H（1A）...F（1） hydrogen bonds via water molecules together with π-π stacking interactions. Molecular geometry of the title compound in the ground state optimized by B3LYP functional with 6-311G＊＊ basis sets indicates that the calculations are in agreement with the experimental data. The preliminary bioassay suggested that the title compound exhibits relatively good fungicidal activity against Fusarium oxysporium fsp.vasinfectum and Dothiorella gregaria.
基金This research was supported by the National Basic Research Program of China (2003CB114400) National Natural Science Foundation of China (20372023)
文摘The title compound, 3-[2-（4-fluoro-phenyl）-ethyl]-5-methyl-4-hydroxyl-4-methyl- 7-methylsulfanyl-3,4-dihydro-pyrido[4,3-d]pyrimidine-8-carbonitrile, has been prepared and detemined by single-crystal X-ray diffraction. The crystal belongs to the triclinic system, space group P1 with a = 6.8754（8）, b = 10.2617（12）, c = 13.3491（16） A, α = 93.163（2）, β = 96.704（2）, γ = 102.421（2）°, V= 910.35（19）A^3, Z= 2, Mr= 370.44, Dc= 1.351 g/cm^3,μ = 0.203 mm^-1,F（000） = 388, the final R = 0.0573 and wR = 0.1497. X-ray analysis reveals that the pyridine and pyrimidine rings are almost coplanar.
