The synthesis of new 4-imino-4H-chromeno[2,3-d]pyrimidin-3(5H)-amine in four steps including one step under microwave dielectric heating is reported. The structural identity of the synthesized compounds was establishe...The synthesis of new 4-imino-4H-chromeno[2,3-d]pyrimidin-3(5H)-amine in four steps including one step under microwave dielectric heating is reported. The structural identity of the synthesized compounds was established according to their spectroscopic analysis, such as FT-IR, NMR and mass spectroscopy. These new compounds were tested for their antiproliferative activities on seven representative human tumoral cell lines (Huh7 D12, Caco2, MDA-MB231, MDA-MB468, HCT116, PC3 and MCF7) and also on fibroblasts. Among them, only the compounds 6c showed micromolar cytotoxic activity on tumor cell lines (1.8 50 50 > 25 μM). Finally, in silico ADMET studies ware performed to investigate the possibility of using of the identified compound 6c as potential anti-tumor compound.展开更多
The crystal structure of the title compound 2-ethoxycarbonylmethyl-8-chloro-3a,4-dihydro-3a-methyl-chromeno[4,3-c]pyrazol-3（2H）-one（C15H15ClN2O4,Mr = 322.74） has been prepared and determined by single-crystal X-ra...The crystal structure of the title compound 2-ethoxycarbonylmethyl-8-chloro-3a,4-dihydro-3a-methyl-chromeno[4,3-c]pyrazol-3（2H）-one（C15H15ClN2O4,Mr = 322.74） has been prepared and determined by single-crystal X-ray diffraction.The crystal is of orthorhombic,space group Pccn with a = 16.7246（10）,b = 19.6626（12）,c = 9.3013（6） ,V = 3058.7（3） 3,Z = 8,Dc = 1.402 g/cm3,μ = 0.269 mm-1,F（000） = 1344,the final R = 0.0506 and wR = 0.1464 for 2568 reflections with I 〉 2σ（I）.In addition,disordered C（14） and C（15） atoms exist in the crystal structure.展开更多
Flavonoids exhibit a wide range of biological activities including anti-inflammatory activity, while some 1,3-benzoxazine derivatives show anti-inflammatory activity. In order to explore the novel anti-inflammatory ag...Flavonoids exhibit a wide range of biological activities including anti-inflammatory activity, while some 1,3-benzoxazine derivatives show anti-inflammatory activity. In order to explore the novel anti-inflammatory agents, based on the principles of bioisosterism and hybridization, ten novel ehromeno[8,7-e][1,3]oxazin-4-ones were syn- thesized and characterized with IR, ^1H NMR, MS and elemental analyses. The anti-inflammatory activities of the target compounds were evaluated via the croton oil-induced ear oedema test in Swiss mice. According to screened resuits, some target compounds show potent anti-inflammatory activity.展开更多
An efficient greener one pot synthesis of dimethyl-dihydro-7H-chromeno[3, 2-h]quinolin-8(9H)-one derivatives has been synthesized through cyclization of aromatic aldehyde, dimidone and 8-hydroxy-quinoline through one-...An efficient greener one pot synthesis of dimethyl-dihydro-7H-chromeno[3, 2-h]quinolin-8(9H)-one derivatives has been synthesized through cyclization of aromatic aldehyde, dimidone and 8-hydroxy-quinoline through one-pot condensation method is described. The synthesized compounds are screened for further biological activities against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Bacillus subtilis, Bacillus using cut plate method and disc diffusion method.展开更多
In this investigation a new strategy involves the one-pot, three-component reaction of malononitrile, salycilaldehyde and phenol derivatives in the presence of high surface area of MgO is extended to the formation of ...In this investigation a new strategy involves the one-pot, three-component reaction of malononitrile, salycilaldehyde and phenol derivatives in the presence of high surface area of MgO is extended to the formation of chromeno[3,4-c]ehromene derivatives in good to excellent yields in a short reaction time. Also, the three component reactions of an aldehyde such as salycilaldehyde and ketones with malononitril for the formation of chromeno[3,4-c]pyridines are investigated.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
This paper describes a very simple, efficient synthesis of quinazolinones and chromeno[d]pyrimidinones from the reaction of aryl aldehydes, urea/thiourea and active methylene compounds（dimedone/4-hydroxycoumarin） us...This paper describes a very simple, efficient synthesis of quinazolinones and chromeno[d]pyrimidinones from the reaction of aryl aldehydes, urea/thiourea and active methylene compounds（dimedone/4-hydroxycoumarin） using nano-sized CuI particles under solvent-free conditions. The highlights of this new method are based on using an effective and recyclable catalyst, affording high yields of products,mild reaction conditions, facile work-up and purification.展开更多
A series of novel 5-（2,3,4,5-tetrahydro-lH-chromeno[2,3-d]pyrimidin-5-yl）pyrimidione derivatives have been synthesized from substituted salicylaldehydes and barbituric acid or 2-thiobarbituric acid in water catalyze...A series of novel 5-（2,3,4,5-tetrahydro-lH-chromeno[2,3-d]pyrimidin-5-yl）pyrimidione derivatives have been synthesized from substituted salicylaldehydes and barbituric acid or 2-thiobarbituric acid in water catalyzed by phase transfer catalysis of triethylbenzyl ammonium chloride （TEBA）. Elemental analysis, IR, 1HNMR, and 13C NMR elucidated the structures of all the newly synthesized compounds. In vitro antimicrobial activities of synthesized compounds have been investigated against Escherichia coli, Bacillus subtilis, Staphylococcus aureus, and Pseudornonas aeruginosa. These newly synthesized derivatives exhibited significant in vitro antibacterial activity.展开更多
Starting from 2-imino-N-phenyl-2H-chromene-3-carbox-amide, (1) a series of functionalized chromenes were achieved;such as, 2-ethoxy-2,3-dihydro-3-phenylchromeno[2,3-d]pyrimidin-4-one (2), and 2-hydrazinyl-2,3-dihydro-...Starting from 2-imino-N-phenyl-2H-chromene-3-carbox-amide, (1) a series of functionalized chromenes were achieved;such as, 2-ethoxy-2,3-dihydro-3-phenylchromeno[2,3-d]pyrimidin-4-one (2), and 2-hydrazinyl-2,3-dihydro-3-phenylchromeno-[2,3-d]pyrimidin-4-one (3). Furthermore, reactions of (3) with some of laboratory available compounds gave pyrazoles (4-9, 12, 13a, 13b), tetrazoles (11), 2-(2-benzylidenehydrazinyl)-3-phenyl-3H-chromeno[2,3-d]pyrimidin4(10H)-oneisoxazoles (14), 5-chloro-1-(4-oxo-3-phenyl-4,10-dihydro-3H-chromeno[2,3-d]pyrimidin-2-yl)-3-phenyl-2, 3-dihydro-1H-pyrazole-4-carbonitrile (17), pyrimidines (28a, b), pyridines (29a-29e, 30, 33a, 33b), benzo[b][1, 4]oxazepin-2- amines (32a, b), 3-chloro-4-(2-imino-2H-chromen-3-yl)-1-phenyl-4-(phenylamino) azetidin-2-one (34a-34e) and 2-(2- imino-2H-chromen-3-yl)-3-phenyl-2-(phenyl amino)thiazolidin-4-onee (35a-35e). The structures of these compounds were established by elemental analysis, IR, MS and NMR spectral analysis.展开更多
文摘The synthesis of new 4-imino-4H-chromeno[2,3-d]pyrimidin-3(5H)-amine in four steps including one step under microwave dielectric heating is reported. The structural identity of the synthesized compounds was established according to their spectroscopic analysis, such as FT-IR, NMR and mass spectroscopy. These new compounds were tested for their antiproliferative activities on seven representative human tumoral cell lines (Huh7 D12, Caco2, MDA-MB231, MDA-MB468, HCT116, PC3 and MCF7) and also on fibroblasts. Among them, only the compounds 6c showed micromolar cytotoxic activity on tumor cell lines (1.8 50 50 > 25 μM). Finally, in silico ADMET studies ware performed to investigate the possibility of using of the identified compound 6c as potential anti-tumor compound.
基金supported by the Medical Research Foundation of Science and Technology of Guangdong Province (No. B2008103)the Natural Science Foundation of Guangdong Province (No. 9451051501002541)
文摘The crystal structure of the title compound 2-ethoxycarbonylmethyl-8-chloro-3a,4-dihydro-3a-methyl-chromeno[4,3-c]pyrazol-3（2H）-one（C15H15ClN2O4,Mr = 322.74） has been prepared and determined by single-crystal X-ray diffraction.The crystal is of orthorhombic,space group Pccn with a = 16.7246（10）,b = 19.6626（12）,c = 9.3013（6） ,V = 3058.7（3） 3,Z = 8,Dc = 1.402 g/cm3,μ = 0.269 mm-1,F（000） = 1344,the final R = 0.0506 and wR = 0.1464 for 2568 reflections with I 〉 2σ（I）.In addition,disordered C（14） and C（15） atoms exist in the crystal structure.
基金Supported by the National Natural Science Foundation of China(No.40724053)
文摘Flavonoids exhibit a wide range of biological activities including anti-inflammatory activity, while some 1,3-benzoxazine derivatives show anti-inflammatory activity. In order to explore the novel anti-inflammatory agents, based on the principles of bioisosterism and hybridization, ten novel ehromeno[8,7-e][1,3]oxazin-4-ones were syn- thesized and characterized with IR, ^1H NMR, MS and elemental analyses. The anti-inflammatory activities of the target compounds were evaluated via the croton oil-induced ear oedema test in Swiss mice. According to screened resuits, some target compounds show potent anti-inflammatory activity.
文摘An efficient greener one pot synthesis of dimethyl-dihydro-7H-chromeno[3, 2-h]quinolin-8(9H)-one derivatives has been synthesized through cyclization of aromatic aldehyde, dimidone and 8-hydroxy-quinoline through one-pot condensation method is described. The synthesized compounds are screened for further biological activities against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Bacillus subtilis, Bacillus using cut plate method and disc diffusion method.
基金the Shahid Bahonar University of Kerman Faculty Research Committee Fund for its support of this investigation
文摘In this investigation a new strategy involves the one-pot, three-component reaction of malononitrile, salycilaldehyde and phenol derivatives in the presence of high surface area of MgO is extended to the formation of chromeno[3,4-c]ehromene derivatives in good to excellent yields in a short reaction time. Also, the three component reactions of an aldehyde such as salycilaldehyde and ketones with malononitril for the formation of chromeno[3,4-c]pyridines are investigated.
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the financial support from the Research Council of East Tehran Branch, Islamic Azad University
文摘This paper describes a very simple, efficient synthesis of quinazolinones and chromeno[d]pyrimidinones from the reaction of aryl aldehydes, urea/thiourea and active methylene compounds（dimedone/4-hydroxycoumarin） using nano-sized CuI particles under solvent-free conditions. The highlights of this new method are based on using an effective and recyclable catalyst, affording high yields of products,mild reaction conditions, facile work-up and purification.
文摘A series of novel 5-（2,3,4,5-tetrahydro-lH-chromeno[2,3-d]pyrimidin-5-yl）pyrimidione derivatives have been synthesized from substituted salicylaldehydes and barbituric acid or 2-thiobarbituric acid in water catalyzed by phase transfer catalysis of triethylbenzyl ammonium chloride （TEBA）. Elemental analysis, IR, 1HNMR, and 13C NMR elucidated the structures of all the newly synthesized compounds. In vitro antimicrobial activities of synthesized compounds have been investigated against Escherichia coli, Bacillus subtilis, Staphylococcus aureus, and Pseudornonas aeruginosa. These newly synthesized derivatives exhibited significant in vitro antibacterial activity.
文摘Starting from 2-imino-N-phenyl-2H-chromene-3-carbox-amide, (1) a series of functionalized chromenes were achieved;such as, 2-ethoxy-2,3-dihydro-3-phenylchromeno[2,3-d]pyrimidin-4-one (2), and 2-hydrazinyl-2,3-dihydro-3-phenylchromeno-[2,3-d]pyrimidin-4-one (3). Furthermore, reactions of (3) with some of laboratory available compounds gave pyrazoles (4-9, 12, 13a, 13b), tetrazoles (11), 2-(2-benzylidenehydrazinyl)-3-phenyl-3H-chromeno[2,3-d]pyrimidin4(10H)-oneisoxazoles (14), 5-chloro-1-(4-oxo-3-phenyl-4,10-dihydro-3H-chromeno[2,3-d]pyrimidin-2-yl)-3-phenyl-2, 3-dihydro-1H-pyrazole-4-carbonitrile (17), pyrimidines (28a, b), pyridines (29a-29e, 30, 33a, 33b), benzo[b][1, 4]oxazepin-2- amines (32a, b), 3-chloro-4-(2-imino-2H-chromen-3-yl)-1-phenyl-4-(phenylamino) azetidin-2-one (34a-34e) and 2-(2- imino-2H-chromen-3-yl)-3-phenyl-2-(phenyl amino)thiazolidin-4-onee (35a-35e). The structures of these compounds were established by elemental analysis, IR, MS and NMR spectral analysis.
