Substituted benzisoselenazolone compounds and use thereof
A technology of benzoisoselenazolone and benzoisoselenazole, which is applied in the field of substituted benzoisoselenazolone derivatives, and can solve the problems that the discovery of anti-tumor active compounds has not yet been reported.
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Embodiment 1、1
[0116] Embodiment 1, 1,2-[bis(5-bromo-1,2-benzisoselenazol-3(2H)-one)]ethane
[0117] Add 5.01ml (7.5mmol) of ethylenediamine to 25ml of analytically pure anhydrous acetonitrile, and slowly drop in 8.3g (2.5mmol) of 5-bromo-2-selenochlorobenzoyl chloride dissolved in 15ml of analytically pure anhydrous acetonitrile A yellow precipitate was formed in the solution, and after the dropwise addition, stirring was continued at room temperature for 3 hours. After the reaction, the solvent was distilled off under reduced pressure, and the residue was stirred overnight with 50ml of water, and the pale yellow precipitate was filtered out, washed several times with a large amount of water, and finally washed several times with ethanol and ether. After drying, 0.3 g of the product was obtained, with a yield of 43%.
[0118] 1 H-NMR (300MHz, DMSO-d 6 )δ: 7.38-7.99 (m, 4H, Ph-H), 4.02 (s, 2H, CH 2 );
[0119] Elemental Analysis C 16 h 12 N 2 o 2 Se 2 Calculated value (%): C45.43 H...
Embodiment 2、1
[0122] Example 2, 1,2-[bis(5-bromo-1,2-benzisoselenazol-3(2H)-one)]butane
[0123] Add 0.85ml (7.5mmol) of 1,4-butanediamine to 25ml of analytically pure dichloromethane, and slowly drop in 8.3g (2.5mmol) of 5-bromo-2-selenochlorobenzoyl chloride dissolved in 15ml of analytically pure dichloromethane under stirring. In the solution of methyl chloride, a yellow precipitate was formed, and after the dropwise addition was completed, stirring was continued at room temperature for 2 hours. After the reaction, the solvent was distilled off under reduced pressure, and the residue was stirred overnight with 50ml of water, and the pale yellow precipitate was filtered out, washed several times with a large amount of water, and finally washed several times with ethanol and ether. After drying, 0.7 g of the product was obtained with a yield of 92.3%. 1 H-NMR (300MHz, DMSO-d 6 )δ: 7.38-7.99 (m, 4H, Ph-H), 4.02 (s, 2H, CH 2 );
[0124] IR(KBr)cm -1 : v C-H :2945,v C＝C(苯环) : 1618, 154...
Embodiment 3、1
[0126] Example 3, 1,2-[bis(5-bromo-1,2-benzisoselenazol-3(2H)-one)]hexane
[0127] Add 0.872g (7.5mmol) of 1,6-hexanediamine to 25ml of analytically pure dichloromethane, and slowly drop in 8.3g (2.5mmol) of 5-bromo-2-selenochlorobenzoyl chloride dissolved in 15ml of analytically pure dichloromethane under stirring. In the solution of methyl chloride, a yellow precipitate was formed, and after the dropwise addition, stirring was continued at room temperature for 3 hours. After the reaction, the solvent was distilled off under reduced pressure, and the residue was stirred with 50ml of water for 16 hours. The pale yellow precipitate was filtered out, washed several times with a large amount of water, and finally washed several times with ethanol and ether. After drying, 0.3 g of the product was obtained, with a yield of 37.6%, M.p. 311-313°C.
[0128] IR(KBr)cm -1 : v C-H :2930, v C＝C(苯环) : 1618, 1547, 1444; v C＝0 :1618;
[0129] 1 H-NMR (300MHz, DMSO-d 6 )δ: 7.38-7.99 (...
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