Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

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

Inactive Publication Date: 2019-12-03
GUANGXI NORMAL UNIV
View PDF5 Cites 0 Cited by
  • 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-iodobenzyl)β-carboline and its synthesis and application

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 1-pyridine-6-methoxy-9-(3-iodobenzyl)-β-carboline, its synthesis and application
  • 1-pyridine-6-methoxy-9-(3-iodobenzyl)-β-carboline, its synthesis and application
  • 1-pyridine-6-methoxy-9-(3-iodobenzyl)-β-carboline, its synthesis and application

Examples

Experimental program
Comparison scheme
Effect test

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...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
diameteraaaaaaaaaa
Login to View More

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

【Technical field】 [0001] The invention relates to the field of medical technology, in particular to a β-carboline compound and its synthesis method and application. 【Background technique】 [0002] 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. [0003] Studies have found that transforming growth factor-β (TGF-β) and its mediated Smad signaling pathway play an importa...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com