Substituted steroid compound and application thereof
A technology of compounds and steroids, applied in the field of steroids and their uses, can solve the problems of stimulating tumor growth and inability to inhibit androgen, and achieve increased drug concentration, good pharmacokinetic parameter characteristics, and excellent inhibitory properties Effect
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Embodiment 1
[0061]Example 1 Preparation 3β-17- (1H-benzo [D] imidazole-2-D-1-yl)-5,16-diene-3-alcohol (compound 7)
[0062]
[0063]Step 1: (3β) -3- (acetyloxy) -17-chlorine-5,16-diene-16-formaldehyde (Compound 2) was synthesized.
[0064]N, N-dimethylformamide (15 ml, 192 mmol) under an ice bath was slowly added dropwise to chloroform (15 mL, 165 mmol) chloroform (45 mL) solution. After the dropwise addition, the chloride (3.00 g, 9.00 mmol) chloroform (45 mL) solution was slowly added dropwise. After the dropwise addition, heated to room temperature, reflux reaction 5HRS. The reaction solution was concentrated under reduced pressure, and the residue was added to ice water, mixed with diethyl ether / ethyl acetate (8 / 2, v / v), combined with a organic layer, washed with saturated brine, dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the concentrated liquid column chromatography was purified from 2.10 g of meter solid, yield: 62.0%. LC-MS (APCI): M / ...
Embodiment 2
[0073]Example 2 Preparation 3β-17- (1H-benzo [D] imidazole-5, 6, 7-d 3-1-yliocrastivheto-5,16-diene-3-alcohol (chemical 合 13)
[0074]
[0075]At room temperature, nitrogen protects anhydrous dimethyl sulfoxide (6 mL) solution to 17-iodine-5,16-diene-3β-alcohol (300 mg, 0.75 mmol), 1H-benzo [D] imidazole- 4, 5, 6, 7-d4(110 mg, 0.90 mmol), L-proline (35 mg, 0.3 mmol), copper (30 mg, 0.15 mmol) and potassium carbonate (259 mg, 1.87 mmol) mixture were overnight at 120 ° C. Cooled to room temperature, add water (25 mL) to quench the reaction, diatomite filtration, and the filtrate was extracted with ethyl acetate (30 mLx 3), combined with organic layers, washed with saturated saline (30 mL), dry alhydrate sodium sulfate, The organic layer was concentrated under reduced pressure, and the concentrated liquid column chromatography was purified from 80 mg of white solid, yield: 27.2%, purity: 99.37%. LC-MS (APCI): M / Z = 393.0 [M + 1]+;1H NMR (300 MHz, MeOD-D) (δ / ppm) 8.18 (S, 1H), 6.08 (DD, ...
Embodiment 3
[0076]Example 3 Preparation 3β-17- (1H-benzo [D] imidazole-4, 5, 6, 7-d 4 -1-yliocomposites - 5,16-diene-3-alcohol(Compound 15)
[0077]
[0078]At room temperature, nitrogen protects anhydrous dimethyl sulfoxide (6 mL) solution to 17-iodine-5,16-diene-3β-alcohol (300 mg, 0.75 mmol), 1H-benzo [D] imidazole- 4, 5, 6, 7-d4(110 mg, 0.90 mmol), L-proline (35 mg, 0.3 mmol), copper (30 mg, 0.15 mmol) and potassium carbonate (259 mg, 1.87 mmol) mixture were overnight at 120 ° C. Cooled to room temperature, add water (25 mL) to quench the reaction, diatomite filtration, and the filtrate was extracted with ethyl acetate (30 mLx 3), combined with organic layers, washed with saturated saline (30 mL), dry alhydrate sodium sulfate, The organic layer was concentrated under reduced pressure, and the concentrated liquid column chromatography was purified from 80 mg of white solid, yield: 27.2%, purity: 99.37%. LC-MS (APCI): M / Z = 393.0 [M + 1]+;1H NMR (300 MHz, MeOD-D) (δ / ppm) 8.18 (S, 1H), 6.08 (DD...
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