Beta-carboline compound as well as synthesis method and application thereof

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

Inactive Publication Date: 2017-09-01
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 th

Method used

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  • Beta-carboline compound as well as synthesis method and application thereof
  • Beta-carboline compound as well as synthesis method and application thereof
  • Beta-carboline compound as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] The structure of Example 1 is the preparation of the compound shown in formula I

[0031] 1) Dissolve 200mg (8.3mmol) of NaH in 1mL N,N-dimethylformamide, stir for 10min, and gradually add 275mg (1mmol) 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 neutral with 300 ml of ammonia, and then extracted with ethyl acetate, and collected In the organic phase, the solvent was removed under reduced pressure to obtain a crude product as a yellow powder;

[0032] 2) The crude product uses a solvent composed of petroleum ether: ethyl acetate=1000:100 (volume ratio) as the eluent, and silica gel column chromatography is used to obtain a pale yellow flocculent product (400mg, yield 81.6%, purity 99.92%) .

[0033] The resulting pale yellow flocculent product was characterize...

Embodiment 2

[0039] The structure of Example 2 is the preparation of the compound shown in formula I

[0040] 1) Dissolve 400mg (16.6mmol) of NaH in 1mL of N,N-dimethylformamide, stir for 10min, and gradually add 550mg (2mmol) 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, extracted with ethyl acetate, and the organic phase is collected , The solvent was removed under reduced pressure to obtain the crude product as a yellow oily liquid;

[0041] 2) The crude product uses a solvent composed of petroleum ether: ethyl acetate=1000:80 (volume ratio) as the eluent, and silica gel column chromatography is used to obtain a pale yellow flocculent product (381 mg, yield 51.6%, purity 99.90%) .

[0042] The obtained light yellow flocculent product was charac...

Embodiment 3

[0043] The structure of Example 3 is the preparation of the compound shown in formula I

[0044] 1) Dissolve 200mg (8.33mmol) of NaH in 5mL N,N-dimethylformamide, stir for 10min, and gradually add 275mg (1mmol) of 1-pyridine-6-methoxy-β-carboline, Stir at room temperature for 10 minutes, and then add 593mg (2mmol) of 3-iodobenzyl bromide dropwise, and continue the reaction at room temperature for about 20 minutes; after the reaction, the resulting reactant is adjusted to neutral with 400ml ammonia water, extracted with ethyl acetate, and the organic phase is collected , The solvent was removed under reduced pressure to obtain the crude product as a yellow oily liquid;

[0045] 2) The crude product uses the solvent composed of petroleum ether: ethyl acetate=1000:50 (volume ratio) as the eluent, and silica gel column chromatography is used to obtain a light yellow flocculent product (440mg, yield 89.8%, purity 99.95%) .

[0046] The obtained light yellow flocculent product was charac...

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Abstract

The invention relates to a beta-carboline compound as well as a synthesis method and application thereof, and belongs to the technical field of medicines. The structure of the compound is shown as a formula I. A primary experiment shows that the compound has remarkable in-vitro renal fibrosis resisting activity and has relatively good potential medical value; the beta-carboline compound can be used for preparing various renal-fibrosis-resisting and chronic-renal-disease-resisting medicines. (The formula I is shown in the description).

Description

[0001] 【Technical Field】 [0002] The invention relates to the technical field of medicine, in particular to a β-carboline compound and its synthesis method and application. [0003] 【Background technique】 [0004] Chronic kidney disease is characterized by renal fibrosis caused by the progressive loss of renal function and the accumulation of extracellular matrix (ECM), which mainly includes glomerular sclerosis and tubulointerstitial fibrosis. Renal interstitial fibrosis is almost the final result of the development of 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 delay the progression of chronic renal disease, greatly reduce the incidence and complications of end-stage renal disease, and reduce the socio-economic burden caused by it. [0005] Studies have found that transforming growth factor-β (TGF-β) and its mediated Smad signaling pat...

Claims

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Application Information

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IPC IPC(8): C07D471/04A61K31/437A61P13/12
CPCC07D471/04
Inventor 彭艳龙靖娴陈胜邓景洪梁铭超黎苏婷
Owner GUANGXI NORMAL UNIV
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