Arbidol

Arbidol (Umifenovir) hydrochloride is an broad-spectrum antiviral chemical agent which can inhibit cell entry of enveloped viruses by blocking viral fusion with host cell membraneIC50 value:Target: Antiviral; Anti-influenza agentin vitro: Arbidol was found to present potent inhibitory activity against enveloped and non-enveloped RNA viruses, including FLU-A, RSV, HRV 14 and CVB3 when added before, during, or after viral infection, with 50% inhibitory concentration (IC50) ranging from 2.7

The reaction flask was placed in an ice-water bath, 19.4 g (0.2 mol) of sulfamic acid was added, 40.5 mg (0.3 mol) of a 30percent aqueous dimethylamine solution, Then, 22.5 g (0.3 mol) of 37percent aqueous formaldehyde solution was added dropwise, Then 1000 mL of water was added, Hydroxy-1-methyl-2- (phenylthiomethyl) indole-3-carboxylic acid ethyl ester (2, 84.0 g, 0.2 mol) was added portionwise, The reaction was stirred at 30 to 40 ° C for 3 h, The reaction was poured into a certain amount of ice water, Adjusting the pH value to 13 or more with 20percent sodium hydroxide, Ice bath cooling, The solid was filtered, Washed with distilled water until neutral, After recrystallization from petroleum ether / ethyl acetate mixed solvent, Arbidol was pure. The above-mentioned Arbiduoer pure by adding acetone, Stirring, control reaction temperature 60 , Concentrated hydrochloric acid was slowly added dropwise to pH 1.0, Dropping continued for 30min, After the completion of dropping reaction 2-3h, Cooled and allowed to stand.Filtration, the kind of white products.The above white product was added to 800 mL of 95percent ethanol, In water (350 mL)Control temperature 25-30 , Stir for 1-2h and let stand.Filtration, drying, To give 91.3 g of (1), as an off-white solid of Arbidol hydrochloride monohydrate, The yield was 85.6percent.It was confirmed by NMR that the synthesized product was consistent with the target product, The content of 99.7percent was detected by high performance liquid chromatography.The reaction flask was placed in an ice-water bath, 19.4 g (0.2 mol) of sulfamic acid was added, 40.5 mg (0.3 mol) of a 30% aqueous dimethylamine solution, Then, 22.5 g (0.3 mol) of 37% aqueous formaldehyde solution was added dropwise, Then 1000 mL of water was added, Hydroxy-1-methyl-2- (phenylthiomethyl) indole-3-carboxylic acid ethyl ester (2, 84.0 g, 0.2 mol) was added portionwise, The reaction was stirred at 30 to 40 C for 3 h, The reaction was poured into a certain amount of ice water, Adjusting the pH value to 13 or more with 20% sodium hydroxide, Ice bath cooling, The solid was filtered, Washed with distilled water until neutral, After recrystallization from petroleum ether / ethyl acetate mixed solvent, Arbidol was pure. The above-mentioned Arbiduoer pure by adding acetone, Stirring, control reaction temperature 60 , Concentrated hydrochloric acid was slowly added dropwise to pH 1.0, Dropping continued for 30min, After the completion of dropping reaction 2-3h, Cooled and allowed to stand.Filtration, the kind of white products.The above white product was added to 800 mL of 95% ethanol, In water (350 mL)Control temperature 25-30 , Stir for 1-2h and let stand.Filtration, drying, To give 91.3 g of (1), as an off-white solid of Arbidol hydrochloride monohydrate, The yield was 85.6%.It was confirmed by NMR that the synthesized product was consistent with the target product, The content of 99.7% was detected by high performance liquid chromatography.General procedure: The umifenovir base was obtained from umifenovir hydrochloridemonohydrate by placing 10 g (18.8 mmol) of umifenovirhydrochloride monohydrate in 200 mL deionized water followedby heating and stirring. After complete dissolution 0.75 g(18.8 mmol) NaOH solution in deionized water was added to theumifenovir hydrochloride solution. The precipitate of umifenovirwas filtered and air dried.Umifenovir base (0.500 g, 1.05 mmol) and 1.05 mmol acid (salicylicacid 0.145 g, gentisic acid 0.160 g, glutaric acid 0.139 g andmaleic acid 0.122 g) were dissolved in 20 mL of hot ethyl acetateand allowed to crystallize.The umifenovir base was obtained from umifenovir hydrochloridemonohydrate by placing 10 g (18.8 mmol) of umifenovirhydrochloride monohydrate in 200 mL deionized water followedby heating and stirring. After complete dissolution 0.75 g(18.8 mmol) NaOH solution in deionized water was added to theumifenovir hydrochloride solution. The precipitate of umifenovirwas filtered and air dried.Umifenovir base (0.500 g, 1.05 mmol) and 1.05 mmol acid (salicylicacid 0.145 g, gentisic acid 0.160 g, glutaric acid 0.139 g andmaleic acid 0.122 g) were dissolved in 20 mL of hot ethyl acetateand allowed to crystallize.General procedure: The umifenovir base was obtained from umifenovir hydrochloridemonohydrate by placing 10 g (18.8 mmol) of umifenovirhydrochloride monohydrate in 200 mL deionized water followedby heating and stirring. After complete dissolution 0.75 g(18.8 mmol) NaOH solution in deionized water was added to theumifenovir hydrochloride solution. The precipitate of umifenovirwas filtered and air dried.Umifenovir base (0.500 g, 1.05 mmol) and 1.05 mmol acid (salicylicacid 0.145 g, gentisic acid 0.160 g, glutaric acid 0.139 g andmaleic acid 0.122 g) were dissolved in 20 mL of hot ethyl acetateand allowed to crystallize.

1. Arbidol is an antiviral treatment for influenza infection.
2. A medicinal agent for treating viral infections.