1-pyridine-6-methoxy-9-(2,3,4,5-tetrafluorobenzyl)β-carboline compound and its synthesis method and application

A synthesis method and compound technology, applied in the field of medicine, can solve the problems of insufficient expansion research of β-carboline alkaloids, limited preparation cost, complicated extraction, etc., and achieve remarkable anti-renal fibrosis activity and good medicinal value. Effect

Inactive Publication Date: 2019-09-03
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, judging from the current research progress, the content of β-carboline alkaloids in natural plants is generally low, and the extraction is relatively complicated, which is not conducive to in-depth research on it. Although it has certain advantages, it is limited by the production cost, so the current research on the expansion of β-carboline alkaloids is still insufficient
This type of compound has a good development prospect, but there is no 1-pyridine-6-methoxy-9-(2,3,4,5-tetrafluorobenzyl)β-carboline and its synthesis and application related reports

Method used

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  • 1-pyridine-6-methoxy-9-(2,3,4,5-tetrafluorobenzyl)β-carboline compound and its synthesis method and application
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  • 1-pyridine-6-methoxy-9-(2,3,4,5-tetrafluorobenzyl)β-carboline compound and its synthesis method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1 structure is as the preparation of the compound shown in formula I

[0031] 1) Dissolve 200 mg (9.3 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 minutes, then add 391.5 mg (1.5 mmol) of 2,3,4,5-tetrafluorobenzyl bromide dropwise, and continue the reaction at room temperature for about 20 minutes; after the reaction, the product obtained is adjusted to neutrality with 300 ml of ammonia water , and extracted with ethyl acetate, the organic phase was collected, and the solvent was removed under reduced pressure to obtain a yellow oily crude product;

[0032] 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 (347mg, yield 79.4%, purity 99.94%) .

[0033] The resulting pale yellow fl...

Embodiment 2

[0039] Embodiment 2 structure is as the preparation of the compound shown in formula I

[0040] Dissolve 400mg (16.6mmol) of NaH in 1mL N, N-dimethylformamide, stir for 10min, and gradually add 550mg (2mmol) of 1-pyridine-6-methoxy-β-carboline, stir at room temperature 10min, then add 391.5mg (1.5mmol) of 2,3,4,5-tetrafluorobenzyl bromide dropwise, and continue the reaction at room temperature for about 20min; Extracted with ethyl acetate, collected the organic phase, and removed the solvent under reduced pressure to obtain the crude product of yellow oily liquid;

[0041] The crude product was subjected to silica gel column chromatography using petroleum ether:ethyl acetate=1000:100 (volume ratio) as the eluent to obtain a light yellow flocculent product (211 mg, yield 48.3%, purity 99.91%).

[0042]The obtained light yellow flocculent product was characterized by NMR, and was determined to be 1-pyridine-6-methoxy-9-(2,3,4,5-tetrafluorobenzyl)β-carboline according to the pre...

Embodiment 3

[0043] Embodiment 3 structure is as the preparation of the compound shown in formula I

[0044] 1) Dissolve 200 mg (9.33 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 524 mg (2 mmol) of 2,3,4,5-tetrafluorobenzyl bromide dropwise, and continue the reaction at room temperature for about 20 min; Extracted with ethyl acetate, collected the organic phase, and removed the solvent under reduced pressure to obtain the crude product of yellow oily liquid;

[0045] 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 (162mg, yield 37.1%, purity 99.90%) .

[0046] The obtained light yellow flocculent product was characterized by NMR, and was determined to be 1-pyridine-6-methoxy-9-(2,3,4,5-tetrafluor...

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Abstract

The invention relates to a beta-carboline compound and a synthesizing method and application thereof, and belongs to the technical field of medicines. The structure of the compound is shown in a formula I. Being proved by preliminary experiment, the beta-carboline compound has the advantages that the activity of resisting renal fibrosis in vitro is obvious, and the good potential medical value is realized; the beta-carboline compound can be applied to prepare various types of medicines for resisting renal fibrosis and chronic renal diseases. The formula I is shown in the description.

Description

[0001] 【Technical field】 [0002] The invention relates to the field of medical technology, in particular to a β-carboline compound and its synthesis method and application. [0003] 【Background technique】 [0004] Chronic kidney disease is characterized by progressive loss of renal function and renal fibrosis caused by massive accumulation of extracellular matrix (ECM), mainly including glomerulosclerosis and tubulointerstitial fibrosis. Renal interstitial fibrosis is the final result of almost all chronic kidney diseases, closely related to the progression of renal failure, and is the main cause of end-stage renal failure. Early intervention and treatment of renal fibrosis will help to delay the progression of chronic kidney disease, greatly reduce the incidence of end-stage renal disease and its complications, and reduce the social and economic burden caused by it. [0005] Studies have found that transforming growth factor-β (TGF-β) and its mediated Smad signaling pathway ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/04A61K31/444A61P13/12
Inventor 彭艳陈胜龙靖娴陈佳敏马乃云潘毓敏
Owner GUANGXI NORMAL UNIV
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