Thioredoxin reductase inhibiter compounds and preparation method and application thereof
A reductase inhibitor, thioredoxin technology, applied in the field of thioredoxin reductase inhibitor compounds and their preparation, can solve the problem of short course of disease
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Embodiment 1
[0019] Example 1 Preparation of compound VI
[0020] synthetic route:
[0021]
[0022] Synthetic steps:
[0023] 1) Dissolve 0.1 mmol of 2-hydroxy-1,3-propanediamine in 20 ml of dichloromethane, dropwise add 0.2 mmol of triethylamine, and stir;
[0024] 2) Dissolve 0.1 mmol of selenium chloride in 10 ml of dichloromethane, and then add it dropwise to the reaction solution obtained in step 1) at room temperature until solids are precipitated.
[0025] MS-FAB (m / z): 453.
Embodiment 2
[0026] Example 2 Preparation of compound VII
[0027] synthetic route:
[0028]
[0029] Synthetic steps:
[0030] 2.1 Synthesis of biselenobis(5-hydroxy)benzoic acid (hereinafter referred to as "Intermediate 4")
[0031] 2.1.1 Preparation of sodium diselenide
[0032] The method disclosed in CN1166651C.
[0033] 2.1.2 Preparation of diazonium salt of 5-hydroxy-2-aminobenzoic acid
[0034] 1) Under ice-salt bath conditions, add 2.8 grams of sodium diselenide in a beaker, then add 6 ml of hydrochloric acid and 24 ml of water;
[0035] 2) Put 1.6 grams of sodium nitrite into a beaker, then add 6ml of water and a small amount of ice cubes;
[0036] 3) Add the reaction solution obtained in step 2) dropwise to the reaction solution obtained in step 1), and fully react to obtain the product.
[0037] 2.1.3 Preparation of Intermediate 4
[0038] 1) Add the diazonium salt prepared in 2.1.2 to the sodium diselenide prepared in 2.1.1 dropwise under the conditions of ice bath...
Embodiment 3
[0051] Example 3 Preparation of compound VIII
[0052] synthetic route:
[0053]
[0054] 3.1 Synthesis of 2-(2-hydroxy)-benzisoselenazol-3-(2H)-one (hereinafter referred to as "Intermediate 1")
[0055] Dissolve 1 g of selenium chlorobenzoyl chloride in 10 ml of dichloromethane, slowly add it dropwise into the dichloromethane solution dissolved in ethanolamine, react at room temperature for 2 hours after the dropwise addition is complete, filter with suction, and dry to obtain the product.
[0056] 3.2 Synthesis of 2-(2-chloro)-benzisoselazol-3-(2H)-one (hereinafter referred to as "Intermediate 2")
[0057] Method 1: Take 1g of intermediate 1 in a round bottom flask, add 7ml of thionyl chloride, reflux for 8 hours, recover thionyl chloride by distillation under reduced pressure, then add ethanol and spin dry to recover thionyl chloride as much as possible. Then, inject water and diethyl ether for extraction, and take the ether layer; spin the ether layer to dry, and ob...
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