1-pyridine-6-methoxy-9-(3-iodobenzyl)-β-carboline, its synthesis and application
A methoxyl and pyridine technology, applied in the field of β-carboline compounds and their synthesis, can solve the problems of production cost limitation, insufficient research on β-carboline alkaloids, in-depth research, etc., and achieve good medicinal value , Anti-renal fibrosis activity significant effect
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Embodiment 1
[0025] Embodiment 1 structure is as the preparation of the compound shown in formula I
[0026] 1) Dissolve 200 mg (8.3 mmol) of NaH in 1 mL of N, N-dimethylformamide, stir for 10 min, and gradually add 275 mg (1 mmol) of 1-pyridine-6-methoxy-β-carboline, Stir at room temperature for 10 min, then add 445 mg (1.5 mmol) of 3-iodobenzyl bromide dropwise, and continue the reaction at room temperature for about 20 min; The organic phase was removed under reduced pressure to obtain the crude product of yellow powder;
[0027] 2) The crude product was subjected to silica gel column chromatography using a solvent composed of petroleum ether:ethyl acetate=1000:100 (volume ratio) as an eluent to obtain a pale yellow flocculent product (400mg, yield 81.6%, purity 99.92%) .
[0028] The resulting pale yellow flocculent product was characterized by nuclear magnetic resonance, and its proton nuclear magnetic resonance spectrum and carbon spectrum were as follows: figure 1 and 2 shown. ...
Embodiment 2
[0034] Embodiment 2 structure is as the preparation of the compound shown in formula I
[0035] 1) Dissolve 400 mg (16.6 mmol) of NaH in 1 mL of N, N-dimethylformamide, stir for 10 min, and gradually add 550 mg (2 mmol) of 1-pyridine-6-methoxy-β-carboline, Stir at room temperature for 10 minutes, then add 445 mg (1.5 mmol) of 3-iodobenzyl bromide dropwise, and continue the reaction at room temperature for about 20 minutes; after the reaction, the product obtained is adjusted to neutrality with 400 ml of ammonia water, extracted with ethyl acetate, and the organic phase is collected , and the solvent was removed under reduced pressure to obtain the crude product of yellow oily liquid;
[0036] 2) The crude product was subjected to silica gel column chromatography using a solvent composed of petroleum ether:ethyl acetate=1000:80 (volume ratio) as an eluent to obtain a pale yellow flocculent product (381mg, yield 51.6%, purity 99.90%) .
[0037] The obtained light yellow floccu...
Embodiment 3
[0038]Embodiment 3 structure is as the preparation of the compound shown in formula I
[0039] 1) Dissolve 200 mg (8.33 mmol) of NaH in 5 mL of N, N-dimethylformamide, stir for 10 min, and gradually add 275 mg (1 mmol) of 1-pyridine-6-methoxy-β-carboline, Stir at room temperature for 10 min, then add 593 mg (2 mmol) of 3-iodobenzyl bromide dropwise, and continue the reaction at room temperature for about 20 min; after the reaction, the resulting reactant is adjusted to neutrality with 400 ml of ammonia water, extracted with ethyl acetate, and the organic phase is collected , and the solvent was removed under reduced pressure to obtain the crude product of yellow oily liquid;
[0040] 2) The crude product was subjected to silica gel column chromatography using a solvent composed of petroleum ether:ethyl acetate=1000:50 (volume ratio) as an eluent to obtain a pale yellow flocculent product (440mg, yield 89.8%, purity 99.95%) .
[0041] The obtained light yellow flocculent prod...
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