To a 96-well dish, 120?L of phosphate buffer remedy (0.1?M, pH?=?8.0, PBS), 20?L of DTNB (3.3?mM in 0.1?M PBS, pH?=?8.0) were added sequentially, 20?L AChE solution (0.2?U/mL in 0.1?M PBS, pH?=?8.0), 20?L of different concentrations from the test remedy, shaken well, and incubated in 37?C for 5?min. possess the potential mainly because drug applicants for the treating Alzheimers disease. activity of 3-arylbenzofuranone derivatives as ChE inhibitors, MAO B inhibitors, and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavengers. The goal of the intensive study can be to display substances that inhibit ChE and MAO, that have the prospect of the treating AD and additional neurodegenerative diseases. Experimental Synthesis methods and Components Melting points were identified utilizing a Thiele tube and were uncorrected. The 1HNMR and 13CNMR spectra had been recorded having a Bruker AM-600 spectrometer (Billercia, MA, USA) with TMS as the inner standard. Chemical substance shifts had been reported at space temperature on the size (ppm) with DMSO-d6 as the solvents and ideals receive in Hertz. Mass spectra had been acquired with an Agilent Capture VL LC/MS spectrometer (Santa Clara, CA, USA). RZ-9618 Microplate recorded The absorbance Audience. Unless noted otherwise, all solvents and reagents were obtainable and utilised without additional purification commercially. General way for synthesis of substances 3a-3d Acquiring the formation of 3, 4, 5-trimethoxy mandelic acidity for example. Additional mandelic acids had been acquired using the same methods. 3,4,5-Trimethoxybenzaldehyde 39.2?g (0.2?mol), TBAB 3.2?g (10?mmol), and chloroform 240?ml were put into a 500?ml three-necked flask built with a dropping funnel and a reflux condenser. The blend was stirred to totally dissolve completely, as well as the temperature grew up to 40?C. A 50% NaOH remedy (40?g of NaOH dissolved in 40?g of drinking water) was slowly added dropwise through a LB-100 dropping funnel to keep up a temp of 45C50?C. Following the TLC recognition reaction was finished, it was permitted to are a symbol of suction and chilling purification. The filtration system cake was cleaned with chloroform 40?ml 3. The ensuing solid blend was acidified with hydrochloric acidity, extracted with ethyl acetate, dried out over anhydrous sodium sulphate, focused, and recrystallisation from ethyl acetate/petroleum ether offered a white solid (produce: 70.5%). General way for the formation of 3-arylbenzofuranone 1C23 Acquiring the formation of 6-hydroxy-3C(3,4,5-trimethoxyphenyl)-benzofuranone for example. Additional 3-arylbenzofuranone substances were acquired using the same methods. 3,4,5-Trimethoxymandelic acidity 4.84?g (20?mmol), resorcin 2.64?g (24?mmol), and boron trifluoride-diethyl ether 20?ml were put into a 100?ml three-necked flask built with LB-100 a reflux condenser and a drying out pipe. The uncooked materials was stirred well to dissolve totally, and keep maintaining the temp at 30C35?C continuous stirring. Following the TLC recognition reaction was finished, the response was permitted to stand for chilling. The reaction remedy was poured right into a beaker including 100?ml of snow drinking water and stirred. After a great deal of white solid was precipitated, it had been permitted to stand, and suction filtered. The filtration system cake was cleaned with saturated sodium bicarbonate remedy, cleaned with distilled drinking water until near natural after that, dried to provide a pale red solid, and recrystallised from methanol to produce white solid (produce: 92.72%). 6-Hydroxyl-3C(4-methoxyphenyl)-benzofuranone (1). White solid, produce 94.14%, m.p. 188C190?C. 1H NMR (600?MHz, DMSO-d6) 9.88 (s, 1H), 7.11 (s, 2H), 7.02???6.86 (m, 3H), 6.63 (d, (%) [M?+?Na]+ 278.9. 5-Hydroxyl-3C(4-methoxyphenyl)-benzofuranone (2). White solid, produce 95.12%, m.p. 164C165?C. 1H NMR (600?MHz, DMSO-d6) 9.38 (s, 1H), 7.13???7.08 (m, 3H), 6.96???6.93 (m, 2H), 6.74 (ddd, (%) [M?+?Na]+ 279.0. 6-Methoxy-3C(4-methoxyphenyl)-benzofuranone (3). White solid, produce 85.32%, m.p. 156C157?C. 1H NMR (600?MHz, DMSO-d6) 7.10 (dd, (%) [M?+?Na]+ 293.0, [M?+?H]+ 271.0. 5-Methoxy-3C(4-methoxyphenyl)-benzofuranone (4). White solid, produce 76.32%, m.p. 126C127?C. 1H NMR (600?MHz, DMSO-d6) 7.23 (d, (%) [M?+?Na]+ 293.0, [M?+?H]+ 271.0. 6,7-Dihydroxy-3C(4-methoxyphenyl)-benzofuranone (5). White solid, produce 91.91%, m.p. 138C140?C. 1H NMR (600?MHz, DMSO-d6) 7.12???7.09 (m, 2H), 6.94???6.91 (m, 2H), 6.59 (d, (%) [M?+?Na]+ 295.0, [M?+?H]+ 273.0. 6-Hydroxy-3C(3,4-dimethoxyphenyl)-benzofuranone (6). White solid, produce 60.47%, m.p. 171C172?C. 1H NMR (600?MHz, DMSO-d6) 9.88 (s, 1H), 7.00 (dd, (%) [M?+?Na]+ 308.9. 5-Hydroxy-6-methoxy-3C(4-methoxyphenyl)-benzofuranone (7). White solid, produce 83.92%, m.p. 151C153?C. 1H NMR (600?MHz, DMSO-d6) 8.92 (s, 1H), 7.11???7.08 (m, 2H), 7.00 (s, 1H), 6.95???6.92 (m, 2H), 6.57 (d, (%) [M?+?Na]+ 309.0. 6-Methoxy-7-hydroxy-3C(4-methoxyphenyl)-benzofuranone (8). White solid, produce 86.36%, m.p. 138C139?C. 1H NMR (600?MHz, DMSO-d6) 9.44 (s, 1H), 7.11 (d, (%) [M?+?Na]+ 309.0, [M?+?H]+ 287.0. 6-Methoxy-3C(3,4-dimethoxyphenyl)-benzofuranone (9). White solid, produce 62.81%, m.p. 125C126?C. 1H NMR (600?MHz, DMSO-d6) 7.12 (d, (%) [M?+?Na]+ 323.0, [M?+?H]+ 301.1, [2M?+?Na]+ 623.1. 5,6-Dimethoxy-3C(4-methoxyphenyl)-benzofuranone (10). White solid, produce 91.11%, m.p. 128C130?C. 1H NMR (600?MHz, DMSO-d6) 7.12 (d, (%) [M?+?Na]+ 323.0, [M?+?H]+ 301.1, [2M?+?Na]+ 623.1. 6-Hydroxy-3C(3,4,5-trimethoxyphenyl)-benzofuranone (11). White solid, produce 92.72%, m.p. 191C193?C. 1H NMR (600?MHz, DMSO-d6) 9.90 (s, 1H), 7.04 (dd, (%)[M?+?Na]+ 339.3. 6-Methoxy-7-hydroxy-3C(3,4-dimethoxyphenyl)-benzofuranone (12). White colored.White solid, produce 91.11%, m.p. had been uncorrected. The 1HNMR and 13CNMR spectra had been recorded using a Bruker AM-600 spectrometer (Billercia, MA, USA) with TMS as the inner standard. Chemical substance shifts had been reported at area temperature on the range (ppm) with DMSO-d6 as the solvents and beliefs receive in Hertz. Mass spectra had been attained with an Agilent Snare VL LC/MS spectrometer (Santa Clara, CA, USA). The absorbance was documented by RZ-9618 Microplate Audience. Unless otherwise observed, all solvents and reagents had been commercially obtainable and utilised without further purification. General way for synthesis of substances 3a-3d Acquiring the formation of 3, 4, 5-trimethoxy mandelic acidity for example. Various other mandelic acids had been attained using the same techniques. 3,4,5-Trimethoxybenzaldehyde 39.2?g (0.2?mol), TBAB 3.2?g (10?mmol), and chloroform 240?ml were put into a 500?ml three-necked flask built with a dropping funnel and a reflux condenser. The mix was completely stirred to totally dissolve, as well as the temperature grew up to 40?C. A 50% NaOH alternative (40?g of NaOH dissolved in 40?g of drinking water) was slowly added dropwise through a dropping funnel to keep a heat range of 45C50?C. Following the TLC recognition reaction was finished, it was permitted to stand for air conditioning and suction purification. The filtration system cake was cleaned with chloroform 40?ml 3. The causing solid mix was acidified with hydrochloric acidity, extracted with ethyl acetate, dried out over anhydrous sodium sulphate, focused, and recrystallisation from ethyl acetate/petroleum ether provided a white solid (produce: 70.5%). General way for the formation of 3-arylbenzofuranone 1C23 Acquiring the formation of 6-hydroxy-3C(3,4,5-trimethoxyphenyl)-benzofuranone for example. Various other 3-arylbenzofuranone substances were attained using the same techniques. 3,4,5-Trimethoxymandelic acidity 4.84?g (20?mmol), resorcin 2.64?g (24?mmol), and boron trifluoride-diethyl ether 20?ml were put into a 100?ml three-necked flask LB-100 built with a reflux condenser and a drying out pipe. The raw materials was stirred well to totally dissolve, and keep maintaining the heat range at 30C35?C continuous stirring. Following the TLC recognition reaction was finished, the response was permitted to stand for air conditioning. The reaction alternative was poured right into a beaker filled with 100?ml of glaciers drinking water and thoroughly stirred. After a great deal of white solid was precipitated, it had been permitted to stand, and suction filtered. The filtration system cake was cleaned with saturated sodium bicarbonate alternative, then cleaned with distilled drinking water until near natural, dried to provide a pale red solid, and recrystallised from methanol to produce white solid (produce: 92.72%). 6-Hydroxyl-3C(4-methoxyphenyl)-benzofuranone (1). White solid, produce 94.14%, m.p. 188C190?C. 1H NMR (600?MHz, DMSO-d6) 9.88 (s, 1H), 7.11 (s, 2H), 7.02???6.86 (m, 3H), 6.63 (d, (%) [M?+?Na]+ 278.9. 5-Hydroxyl-3C(4-methoxyphenyl)-benzofuranone (2). White solid, produce 95.12%, m.p. 164C165?C. 1H NMR (600?MHz, DMSO-d6) 9.38 (s, 1H), 7.13???7.08 (m, 3H), 6.96???6.93 (m, 2H), 6.74 (ddd, (%) [M?+?Na]+ 279.0. 6-Methoxy-3C(4-methoxyphenyl)-benzofuranone (3). White solid, produce 85.32%, m.p. 156C157?C. 1H NMR (600?MHz, DMSO-d6) 7.10 (dd, (%) [M?+?Na]+ 293.0, [M?+?H]+ 271.0. 5-Methoxy-3C(4-methoxyphenyl)-benzofuranone (4). White solid, produce 76.32%, m.p. 126C127?C. 1H NMR (600?MHz, DMSO-d6) 7.23 (d, (%) [M?+?Na]+ 293.0, [M?+?H]+ 271.0. 6,7-Dihydroxy-3C(4-methoxyphenyl)-benzofuranone (5). White solid, produce 91.91%, m.p. 138C140?C. 1H NMR (600?MHz, DMSO-d6) 7.12???7.09 (m, 2H), 6.94???6.91 (m, 2H), 6.59 (d, (%) [M?+?Na]+ 295.0, [M?+?H]+ 273.0. 6-Hydroxy-3C(3,4-dimethoxyphenyl)-benzofuranone (6). White solid, produce 60.47%, m.p. 171C172?C. 1H NMR (600?MHz, DMSO-d6) 9.88 (s, 1H), 7.00 (dd, (%) [M?+?Na]+ 308.9. 5-Hydroxy-6-methoxy-3C(4-methoxyphenyl)-benzofuranone (7). White solid, produce 83.92%, m.p. 151C153?C. 1H NMR (600?MHz, DMSO-d6) 8.92 (s, 1H), 7.11???7.08 (m, 2H), 7.00 (s, 1H), 6.95???6.92 (m, 2H), 6.57 (d, (%) [M?+?Na]+ 309.0. 6-Methoxy-7-hydroxy-3C(4-methoxyphenyl)-benzofuranone (8). White solid, produce 86.36%, m.p. 138C139?C. 1H NMR (600?MHz, DMSO-d6) 9.44 (s, 1H), 7.11 (d, (%) [M?+?Na]+ 309.0, [M?+?H]+ 287.0. 6-Methoxy-3C(3,4-dimethoxyphenyl)-benzofuranone (9). White solid, produce 62.81%, m.p. 125C126?C. 1H NMR (600?MHz, DMSO-d6) 7.12 (d, (%) [M?+?Na]+ 323.0, [M?+?H]+ 301.1, [2M?+?Na]+ 623.1. 5,6-Dimethoxy-3C(4-methoxyphenyl)-benzofuranone (10). White solid, produce 91.11%, m.p. 128C130?C. 1H NMR (600?MHz, DMSO-d6) 7.12 (d, (%) [M?+?Na]+ 323.0, [M?+?H]+ 301.1, [2M?+?Na]+ 623.1. 6-Hydroxy-3C(3,4,5-trimethoxyphenyl)-benzofuranone (11). White solid, produce 92.72%, m.p. 191C193?C. 1H NMR.Light solid, produce 76.32%, m.p. the treating AD and various other neurodegenerative illnesses. Experimental Synthesis Strategies and Components Melting factors LB-100 were determined utilizing a Thiele pipe and were uncorrected. The 1HNMR and 13CNMR spectra had been recorded using a Bruker AM-600 spectrometer (Billercia, MA, USA) with TMS as the inner standard. Chemical substance shifts had been reported at area temperature on the range (ppm) with DMSO-d6 as the solvents and beliefs receive in Hertz. Mass spectra had been attained with an Agilent Snare VL LC/MS spectrometer (Santa Clara, CA, USA). The absorbance was documented by RZ-9618 Microplate Audience. Unless otherwise observed, all solvents and reagents had been commercially obtainable and utilised without further purification. General way for synthesis of substances 3a-3d Acquiring the formation of 3, 4, 5-trimethoxy mandelic acidity for example. Various other mandelic acids were obtained using the same procedures. 3,4,5-Trimethoxybenzaldehyde 39.2?g (0.2?mol), TBAB 3.2?g (10?mmol), and chloroform 240?ml were added to a 500?ml three-necked flask equipped with a dropping funnel and a reflux condenser. The combination was thoroughly stirred to completely dissolve, and the temperature was raised to 40?C. A 50% NaOH answer (40?g of NaOH dissolved in 40?g of water) was slowly added dropwise through a dropping funnel to maintain a heat of 45C50?C. After the TLC detection reaction was completed, it was allowed to stand for cooling and suction filtration. The filter cake was washed with chloroform 40?ml 3. The producing solid combination was acidified with hydrochloric acid, extracted with ethyl acetate, dried over anhydrous sodium sulphate, concentrated, and recrystallisation from ethyl acetate/petroleum ether gave a white solid (yield: 70.5%). General method for the synthesis of 3-arylbenzofuranone 1C23 Taking the synthesis of 6-hydroxy-3C(3,4,5-trimethoxyphenyl)-benzofuranone as an example. Other 3-arylbenzofuranone compounds were obtained using the same procedures. 3,4,5-Trimethoxymandelic acid 4.84?g (20?mmol), resorcin 2.64?g (24?mmol), and boron trifluoride-diethyl ether 20?ml were added to a 100?ml three-necked flask equipped with a reflux condenser and a drying tube. The raw material was stirred well to completely dissolve, and maintain the heat at 30C35?C continuous stirring. After the TLC detection reaction was completed, the reaction was allowed to stand for cooling. The reaction answer was poured into a beaker made up of 100?ml of ice water and thoroughly stirred. After a large amount of white solid was precipitated, it was allowed to stand, and suction filtered. The filter cake was washed with saturated sodium bicarbonate answer, then washed with distilled water until near neutral, dried to give a pale pink solid, and recrystallised from methanol to yield white solid (yield: 92.72%). 6-Hydroxyl-3C(4-methoxyphenyl)-benzofuranone (1). White solid, yield 94.14%, m.p. 188C190?C. 1H NMR (600?MHz, DMSO-d6) 9.88 (s, 1H), 7.11 (s, 2H), 7.02???6.86 (m, 3H), 6.63 (d, (%) [M?+?Na]+ 278.9. 5-Hydroxyl-3C(4-methoxyphenyl)-benzofuranone (2). White solid, yield 95.12%, m.p. 164C165?C. 1H NMR (600?MHz, DMSO-d6) 9.38 (s, 1H), 7.13???7.08 (m, 3H), 6.96???6.93 (m, 2H), 6.74 (ddd, (%) [M?+?Na]+ 279.0. 6-Methoxy-3C(4-methoxyphenyl)-benzofuranone (3). White solid, yield 85.32%, m.p. 156C157?C. 1H NMR (600?MHz, DMSO-d6) 7.10 (dd, (%) [M?+?Na]+ 293.0, [M?+?H]+ 271.0. 5-Methoxy-3C(4-methoxyphenyl)-benzofuranone (4). White solid, yield 76.32%, m.p. 126C127?C. 1H NMR (600?MHz, DMSO-d6) 7.23 (d, (%) [M?+?Na]+ 293.0, [M?+?H]+ 271.0. 6,7-Dihydroxy-3C(4-methoxyphenyl)-benzofuranone (5). White solid, yield 91.91%, m.p. 138C140?C. 1H NMR (600?MHz, DMSO-d6) 7.12???7.09 (m, 2H), 6.94???6.91 (m, 2H), 6.59 (d, (%) [M?+?Na]+ 295.0, [M?+?H]+ 273.0. 6-Hydroxy-3C(3,4-dimethoxyphenyl)-benzofuranone (6). White solid, yield 60.47%, m.p. 171C172?C. 1H NMR (600?MHz, DMSO-d6) 9.88 (s, 1H), 7.00 (dd, (%) [M?+?Na]+ 308.9. 5-Hydroxy-6-methoxy-3C(4-methoxyphenyl)-benzofuranone (7). White solid, yield 83.92%, m.p. 151C153?C. 1H NMR (600?MHz, DMSO-d6) 8.92 (s, 1H), 7.11???7.08 (m, 2H), 7.00 (s, 1H), 6.95???6.92 (m, 2H), 6.57 (d, (%) [M?+?Na]+ 309.0. 6-Methoxy-7-hydroxy-3C(4-methoxyphenyl)-benzofuranone (8). White solid, yield 86.36%, m.p. 138C139?C. 1H NMR (600?MHz, DMSO-d6) 9.44 (s,.B is a double reciprocal plot of compound 13 inhibition of BuChE. Molecular modelling To clarify the mechanism of the compounds inhibitory activity around the enzyme, the binding model of the active and inactive compounds to the active site was compared. with a Bruker AM-600 spectrometer (Billercia, MA, USA) with TMS as the internal standard. Chemical shifts were reported at room temperature on a level (ppm) with DMSO-d6 as the solvents and values are given in Hertz. Mass spectra were obtained with an Agilent Trap VL LC/MS spectrometer (Santa Clara, CA, USA). The absorbance was recorded by RZ-9618 Microplate Reader. Unless otherwise noted, all solvents and reagents were commercially available and used without further purification. General method for synthesis of compounds 3a-3d Taking the synthesis of 3, 4, 5-trimethoxy mandelic acid as an example. Other mandelic acids were obtained using the same procedures. 3,4,5-Trimethoxybenzaldehyde 39.2?g (0.2?mol), TBAB 3.2?g (10?mmol), and chloroform 240?ml were added to a 500?ml three-necked flask equipped with a dropping funnel and a reflux condenser. The combination was thoroughly stirred to completely dissolve, and the temperature was raised to 40?C. A 50% NaOH answer (40?g of NaOH dissolved in 40?g of water) was slowly added dropwise through a dropping funnel to maintain a heat of 45C50?C. After the TLC detection reaction was completed, it was allowed to stand for cooling and suction filtration. The filter cake was washed with chloroform 40?ml 3. The producing solid combination was acidified with hydrochloric acid, extracted with ethyl acetate, dried over anhydrous sodium sulphate, concentrated, and recrystallisation from ethyl acetate/petroleum ether gave a white solid (yield: 70.5%). General method for the synthesis of 3-arylbenzofuranone 1C23 Taking the synthesis of 6-hydroxy-3C(3,4,5-trimethoxyphenyl)-benzofuranone as an example. Other 3-arylbenzofuranone compounds were obtained using the same procedures. 3,4,5-Trimethoxymandelic acid 4.84?g (20?mmol), resorcin 2.64?g (24?mmol), and boron trifluoride-diethyl ether 20?ml were added to a 100?ml three-necked flask equipped with a reflux condenser and a drying tube. The raw material was stirred well to completely dissolve, and maintain the heat at 30C35?C continuous stirring. After the TLC detection reaction was completed, the reaction was allowed to stand for cooling. The reaction solution was poured into a beaker containing 100?ml of ice water and thoroughly stirred. After a large amount of white solid was precipitated, it was allowed to stand, and suction filtered. The filter cake was washed with saturated sodium bicarbonate solution, then washed with distilled water until near neutral, dried to give a pale pink solid, and recrystallised from methanol to yield white solid (yield: 92.72%). 6-Hydroxyl-3C(4-methoxyphenyl)-benzofuranone (1). White solid, yield 94.14%, m.p. 188C190?C. 1H NMR (600?MHz, DMSO-d6) 9.88 (s, 1H), 7.11 (s, 2H), 7.02???6.86 (m, 3H), 6.63 (d, (%) [M?+?Na]+ 278.9. 5-Hydroxyl-3C(4-methoxyphenyl)-benzofuranone (2). White solid, yield 95.12%, m.p. 164C165?C. 1H NMR (600?MHz, DMSO-d6) 9.38 (s, 1H), 7.13???7.08 (m, 3H), 6.96???6.93 (m, 2H), 6.74 (ddd, (%) [M?+?Na]+ 279.0. 6-Methoxy-3C(4-methoxyphenyl)-benzofuranone (3). White solid, yield 85.32%, m.p. 156C157?C. 1H NMR (600?MHz, DMSO-d6) 7.10 (dd, (%) [M?+?Na]+ 293.0, [M?+?H]+ 271.0. 5-Methoxy-3C(4-methoxyphenyl)-benzofuranone (4). White solid, yield 76.32%, m.p. 126C127?C. 1H NMR (600?MHz, DMSO-d6) 7.23 (d, (%) [M?+?Na]+ 293.0, [M?+?H]+ 271.0. 6,7-Dihydroxy-3C(4-methoxyphenyl)-benzofuranone (5). White solid, yield 91.91%, m.p. 138C140?C. 1H NMR (600?MHz, DMSO-d6) 7.12???7.09 (m, 2H), 6.94???6.91 (m, 2H), 6.59 (d, (%) [M?+?Na]+ 295.0, [M?+?H]+ 273.0. 6-Hydroxy-3C(3,4-dimethoxyphenyl)-benzofuranone (6). White solid, yield 60.47%, m.p. 171C172?C. 1H NMR (600?MHz, DMSO-d6) 9.88 (s, 1H), 7.00 (dd, (%) [M?+?Na]+ 308.9. 5-Hydroxy-6-methoxy-3C(4-methoxyphenyl)-benzofuranone (7). White solid,.138C139?C. Materials and methods Melting points were determined using a Thiele tube and were uncorrected. The 1HNMR and 13CNMR spectra LB-100 were recorded with a Bruker AM-600 spectrometer (Billercia, MA, USA) with TMS as the internal standard. Chemical shifts were reported at room temperature on a scale (ppm) with DMSO-d6 as the solvents and Tpo values are given in Hertz. Mass spectra were obtained with an Agilent Trap VL LC/MS spectrometer (Santa Clara, CA, USA). The absorbance was recorded by RZ-9618 Microplate Reader. Unless otherwise noted, all solvents and reagents were commercially available and used without further purification. General method for synthesis of compounds 3a-3d Taking the synthesis of 3, 4, 5-trimethoxy mandelic acid as an example. Other mandelic acids were obtained using the same procedures. 3,4,5-Trimethoxybenzaldehyde 39.2?g (0.2?mol), TBAB 3.2?g (10?mmol), and chloroform 240?ml were added to a 500?ml three-necked flask equipped with a dropping funnel and a reflux condenser. The mixture was thoroughly stirred to completely dissolve, and the temperature was raised to 40?C. A 50% NaOH solution (40?g of NaOH dissolved in 40?g of water) was slowly added dropwise through a dropping funnel to maintain a temperature of 45C50?C. After the TLC detection reaction was completed, it was allowed to stand for cooling and suction filtration. The filter cake was washed with chloroform 40?ml 3. The resulting solid mixture was acidified with hydrochloric acid, extracted with ethyl acetate, dried over anhydrous sodium sulphate, concentrated, and recrystallisation from ethyl acetate/petroleum ether gave a white solid (yield: 70.5%). General method for the synthesis of 3-arylbenzofuranone 1C23 Taking the synthesis of 6-hydroxy-3C(3,4,5-trimethoxyphenyl)-benzofuranone as an example. Other 3-arylbenzofuranone compounds were obtained using the same procedures. 3,4,5-Trimethoxymandelic acid 4.84?g (20?mmol), resorcin 2.64?g (24?mmol), and boron trifluoride-diethyl ether 20?ml were added to a 100?ml three-necked flask equipped with a reflux condenser and a drying tube. The raw material was stirred well to completely dissolve, and maintain the temperature at 30C35?C continuous stirring. After the TLC detection reaction was completed, the reaction was allowed to stand for cooling. The reaction solution was poured into a beaker containing 100?ml of ice water and thoroughly stirred. After a large amount of white solid was precipitated, it was allowed to stand, and suction filtered. The filter cake was washed with saturated sodium bicarbonate solution, then washed with distilled water until near neutral, dried to give a pale pink solid, and recrystallised from methanol to yield white solid (yield: 92.72%). 6-Hydroxyl-3C(4-methoxyphenyl)-benzofuranone (1). White solid, yield 94.14%, m.p. 188C190?C. 1H NMR (600?MHz, DMSO-d6) 9.88 (s, 1H), 7.11 (s, 2H), 7.02???6.86 (m, 3H), 6.63 (d, (%) [M?+?Na]+ 278.9. 5-Hydroxyl-3C(4-methoxyphenyl)-benzofuranone (2). White solid, yield 95.12%, m.p. 164C165?C. 1H NMR (600?MHz, DMSO-d6) 9.38 (s, 1H), 7.13???7.08 (m, 3H), 6.96???6.93 (m, 2H), 6.74 (ddd, (%) [M?+?Na]+ 279.0. 6-Methoxy-3C(4-methoxyphenyl)-benzofuranone (3). White solid, yield 85.32%, m.p. 156C157?C. 1H NMR (600?MHz, DMSO-d6) 7.10 (dd, (%) [M?+?Na]+ 293.0, [M?+?H]+ 271.0. 5-Methoxy-3C(4-methoxyphenyl)-benzofuranone (4). White solid, yield 76.32%, m.p. 126C127?C. 1H NMR (600?MHz, DMSO-d6) 7.23 (d, (%) [M?+?Na]+ 293.0, [M?+?H]+ 271.0. 6,7-Dihydroxy-3C(4-methoxyphenyl)-benzofuranone (5). White solid, yield 91.91%, m.p. 138C140?C. 1H NMR (600?MHz, DMSO-d6) 7.12???7.09 (m, 2H), 6.94???6.91 (m, 2H), 6.59 (d, (%) [M?+?Na]+ 295.0, [M?+?H]+ 273.0. 6-Hydroxy-3C(3,4-dimethoxyphenyl)-benzofuranone (6). White solid, yield 60.47%, m.p. 171C172?C. 1H NMR (600?MHz, DMSO-d6) 9.88 (s, 1H), 7.00 (dd, (%) [M?+?Na]+ 308.9. 5-Hydroxy-6-methoxy-3C(4-methoxyphenyl)-benzofuranone (7). White solid, yield 83.92%, m.p. 151C153?C. 1H NMR (600?MHz, DMSO-d6) 8.92 (s, 1H), 7.11???7.08 (m, 2H), 7.00 (s, 1H), 6.95???6.92 (m, 2H), 6.57 (d, (%) [M?+?Na]+ 309.0. 6-Methoxy-7-hydroxy-3C(4-methoxyphenyl)-benzofuranone (8). White solid, yield 86.36%, m.p. 138C139?C. 1H NMR (600?MHz, DMSO-d6) 9.44 (s, 1H), 7.11 (d, (%) [M?+?Na]+ 309.0, [M?+?H]+ 287.0. 6-Methoxy-3C(3,4-dimethoxyphenyl)-benzofuranone (9). White solid, yield 62.81%, m.p. 125C126?C. 1H NMR (600?MHz, DMSO-d6) 7.12 (d, (%) [M?+?Na]+ 323.0, [M?+?H]+ 301.1, [2M?+?Na]+ 623.1. 5,6-Dimethoxy-3C(4-methoxyphenyl)-benzofuranone (10). White solid, yield 91.11%, m.p. 128C130?C. 1H NMR (600?MHz, DMSO-d6) 7.12 (d, (%) [M?+?Na]+ 323.0, [M?+?H]+ 301.1, [2M?+?Na]+ 623.1. 6-Hydroxy-3C(3,4,5-trimethoxyphenyl)-benzofuranone (11). White solid, yield 92.72%, m.p. 191C193?C. 1H NMR (600?MHz, DMSO-d6) 9.90 (s, 1H), 7.04 (dd, (%)[M?+?Na]+ 339.3. 6-Methoxy-7-hydroxy-3C(3,4-dimethoxyphenyl)-benzofuranone (12). White solid, yield 78.13%, m.p. 135C137?C. 1H NMR (600?MHz, DMSO-d6) 9.43 (s, 1H), 6.93 (d, (%) [M?+?Na]+ 339.0, [M?+?H]+ 317.1, [2M?+?Na]+ 655.1. 5-Hydroxy-6-methoxy-3C(3,4-dimethoxyphenyl)-benzofuranone (13). White solid, yield 79.11%, m.p. 154C155?C. 1H NMR (600?MHz, DMSO-d6) 8.91 (d, (%) [M?+?Na]+ 339.0, [2M?+?Na]+ 655.1. 5-Hydroxy-3C(3,4,5-trimethoxyphenyl)-benzofuranone (14). White solid, yield 50.68%, m.p. 188C189?C. 1H NMR (600?MHz, DMSO-d6).
To a 96-well dish, 120?L of phosphate buffer remedy (0