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Beta-carboline compound and synthetic method and application thereof

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

Inactive Publication Date: 2017-09-08
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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 are no related reports on 1-pyridine-6-methoxy-9-(3-methylbenzyl)β-carboline and its synthesis and application

Method used

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  • Beta-carboline compound and synthetic method and application thereof
  • Beta-carboline compound and synthetic method and application thereof
  • Beta-carboline compound and synthetic method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1 structure is as the preparation of the compound shown in formula I

[0036] 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 555 mg (3 mmol) of 3-methylbenzyl 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;

[0037] 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 an orange-yellow powder product (654 mg, yield 85.8%, purity 99.90%).

[0038] The obtained orange-yellow powder...

Embodiment 2

[0044] Embodiment 2 structure is as the preparation of the compound shown in formula I

[0045] Dissolve 200 mg (8.33 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, and stir at room temperature 10min, then add 277.5mg (1.5mmol) of 3-methylbenzyl bromide dropwise, and continue the reaction at room temperature for about 20min; after the reaction, the product obtained is adjusted to neutrality with 400ml 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;

[0046] The crude product was subjected to silica gel column chromatography using petroleum ether:ethyl acetate=1000:80 (volume ratio) as the eluent to obtain an orange-yellow powder product (248 mg, yield 65.4%, purity 99.93%).

[0047] The obtained orange-yellow powder product was characterized by NMR and...

Embodiment 3

[0048] Embodiment 3 structure is as the preparation of the compound shown in formula I

[0049] 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 277.5 mg (1.5 mmol) of 3-methylbenzyl 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 oily liquid;

[0050] 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 an orange-yellow powder product (286 mg, yield 76.3%, purity 99.90%).

[0051] The obtained orange-yellow powder product was characterized by NMR and determined to be 1-pyridine-6-methoxy-9-(3-methylbenzyl)β-carboline described in the present invention.

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Abstract

The invention relates to a beta-carboline compound and a synthetic method and application thereof, and belongs to the technical field of medicine. The structure of the compound is shown as the formula I (the formula I is shown in the specification). After an initial test, it is indicated that the in-vitro anti-renal-fibrosis activity of the compound is remarkable, the treatment effect on renal interstitial fibrosis caused by obstruction of the left ureter of a Balb / c mouse is good, the good potential medical value is achieved, and the beta-carboline compound and the synthetic method and application thereof can be used for preparing various kinds of anti-renal-fibrosis and anti-chronic-kidney-disease medicine.

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 Applications(China)
IPC IPC(8): C07D471/04A61K31/444A61P13/12
CPCC07D471/04
Inventor 彭艳陈胜龙靖娴张国海朱艳宏杨阳
Owner GUANGXI NORMAL UNIV
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