Beta-carboline compound and synthesizing method and application thereof

A synthetic method and compound technology, applied in the field of medicine, can solve the problems of limited production cost, insufficient research on β-carboline alkaloids, and low content, and achieve good medicinal value and significant anti-renal fibrosis activity Effect

Inactive Publication Date: 2017-08-01
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented technology allows scientists to create new chemical structures called beta carbolines (BCH). These molecules have unique properties which make them useful against different types of diseases such as renal failure or chronic nephritis. They also show promise in treating these conditions by reducing inflammations caused by excessive protein deposition during their treatment process.

Problems solved by technology

Technologies aim at finding new drugs capable of preventing and reversely controlling various types of renally damaged tissue called necroinflammations associated with diabetes. These include both primary and secondary causes like autoimmune disorders, metabolism abnormalities, inflammatory responses, oxidative stress syndrome, hypertension, cardiovascular events, and obstructive pulmonary vasculature dysfunction. Current methods involve targeting specific proteins within these organs, either alone or combined together through gene manipulations.

Method used

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

Examples

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 pale yellow flocculent product was characterized by NMR, and was determined to be 1-pyridine-6-methoxy-9-(2,3,4,5-tetrafluorobenzyl)β-carboline described in the pres...

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 pale yellow flocculent product was characterized by NMR, and was determined to be 1-pyridine-6-methoxy-9-(2,3,4,5-tetrafluoro...

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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

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Claims

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Application Information

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Owner GUANGXI NORMAL UNIV
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