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

7 site-connected bis(beta-carboline alkaloid) compound and its preparation method, pharmaceutical composition and use

A compound, carboline base technology, applied in the preparation of anti-tumor drugs, the field of 7-position double β-carboline base compounds, can solve the problem of not disclosing the anti-tumor effect

Inactive Publication Date: 2015-07-01
XINJIANG HUASHIDAN PHARMA RES
View PDF3 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] According to the synthesis method of Winckler et al., Zheng et al. (2011) synthesized the 9-position methylene bridge link and 11 C-labeled bis-3,4-dihydro-β-carbolines and bis-β-carbolines were found to be useful as novel imaging agents for positive emission tomography Imaging of acetylcholinesterase in Alzheimer's disease (AD) patients, but no disclosure of antitumor effects of this class of compounds

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
  • 7 site-connected bis(beta-carboline alkaloid) compound and its preparation method, pharmaceutical composition and use
  • 7 site-connected bis(beta-carboline alkaloid) compound and its preparation method, pharmaceutical composition and use
  • 7 site-connected bis(beta-carboline alkaloid) compound and its preparation method, pharmaceutical composition and use

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0178]

[0179] 1,9-Dimethyl-β-carboline-7-ol:

[0180] Synthesis of 1,9-Dimethyl-β-carboline-7-ol:

[0181] (a) Synthesis of 7‐methoxy‐1,9‐dimethyl‐β‐carboline:

[0182] Add dehydrohaeline (2.12g, 10mmol) and DMF (50ml) into a 100ml eggplant-shaped bottle, stir well, add NaH (0.8g, 20mmol) and stir for 10min, then add iodomethane (1.73ml, 15mmol) and stir at room temperature , TLC tracking detection. After the reaction was completed, the reaction solution was poured into 200 ml of ice water, and extracted three times with ethyl acetate. The organic phases were combined, washed with water and saturated brine. Add saturated hydrogen chloride-ethanol solution to the organic phase to pH = 2-3, distill under reduced pressure, recrystallize from acetone, and filter to obtain a yellow solid. The above solid was dissolved in 100ml of water, with NaHCO 3 Adjust pH=8‐9, extract with ethyl acetate three times, combine organic phases, wash with water and saturated brine. The org...

preparation example 2

[0186]

[0187] Synthesis of 9‐ethyl‐1‐methyl‐β‐carboline‐7‐ol:

[0188] (a) Synthesis of 9‐ethyl‐7‐methoxy‐1‐methyl‐β‐carboline:

[0189] Add dehydrohaeline (2.12g, 10mmol) and DMF (50ml) into a 100ml eggplant-shaped bottle, stir well, add NaH (0.8g, 20mmol) and stir for 10min, then add iodoethane (1.6ml, 15mmol) at room temperature Stirring, TLC follow-up detection. After the reaction was completed, the reaction solution was poured into 200 ml of ice water, and extracted three times with ethyl acetate. The organic phases were combined, washed with water and saturated brine. Add saturated hydrogen chloride-ethanol solution to the organic phase to pH = 2-3, distill under reduced pressure, crystallize acetone, and filter to obtain a yellow solid. The above solid was dissolved in 100ml of water, with NaHCO 3 Adjust the pH to 8‐9, extract 3 times with ethyl acetate, combine the organic phases, wash with water, and wash with saturated brine. The organic phase was dehydrate...

preparation example 3

[0193]

[0194] Synthesis of 9-n-butyl-1-methyl-β-carboline-7-ol:

[0195] (a) Synthesis of 9-n-butyl-7-methoxy-1-methyl-β-carboline:

[0196] Add dehydrobamaline (2.12g, 10mmol) and DMF (50ml) into a 100ml eggplant-shaped bottle, stir well, add NaH (0.8g, 20mmol) and stir for 10min, then add iodo-n-butane (1.38ml, 15mmol ) Stirring at room temperature, followed by TLC detection. After the reaction was completed, the reaction solution was poured into 200 ml of ice water, and extracted three times with ethyl acetate. The organic phases were combined, washed with water and saturated brine. Add saturated hydrogen chloride-ethanol solution to the organic phase to pH = 2-3, distill under reduced pressure, crystallize acetone, and filter to obtain a yellow solid. The above solid was dissolved in 100ml of water, with NaHCO 3 Adjust the pH to 8‐9, extract 3 times with ethyl acetate, combine the organic phases, wash with water, and wash with saturated brine. The organic phase w...

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

No PUM Login to View More

Abstract

The invention discloses a 7 site-connected bis(beta-carboline alkaloid) compound and its preparation method, pharmaceutical composition and use. The bis(beta-carboline alkaloid) compound and its medicinal salt are shown in the general formula I. The bis(beta-carboline alkaloid) compound is prepared by condensation of a beta-carboline intermediate and dihalogenated alkane. The invention discloses a pharmaceutical composition. The pharmaceutical composition comprises an effective dose of the bis(beta-carboline alkaloid) compound shown in the formula I and pharmaceutically acceptable carriers. The invention relates to a use of the bis(beta-carboline alkaloid) compound in preparation of drugs for resisting cancers such as melanoma, stomach cancer, lung cancer, breast cancer, kidney cancer, liver cancer, human oral epidermoid carcinoma, cervical carcinoma, ovarian cancer, pancreas cancer, prostate cancer and colorectal carcinoma.

Description

technical field [0001] The invention relates to a class of 7-position-connected bis-carboline base compounds and pharmaceutically acceptable salts thereof, a preparation method thereof, a pharmaceutical composition of such compounds, and an application thereof in the preparation of antitumor drugs; belonging to medicine technology field. Background technique [0002] Jiang et al. (2002) reported the design and synthesis of bis-3,4-dihydro-β-carbolines and bis-β-carbolines linked by a methylene bridge at the 1-position, and found that such bis-β-carbolines Alkali is cytotoxic to the L1210 cell line. [0003] Cook et al. (2005, 2010) reported the synthesis of bis-β-carbolines linked by a 6-alkyne bridge, and subsequently confirmed that the bis-β-carboline bases are sensitive to benzodiazepine receptors (Bz) and γ-aminobutyric acid Acid (GABA) receptors have good affinity. [0004] Winckler et al. (2010) designed bis-3,4-dihydro-β-carboline and bis-β-carboline compounds conn...

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
IPC IPC(8): C07D519/00C07D471/04A61K31/437A61P35/00
Inventor 马芹王子厚郭亮范文玺武嘉林陈雪梅周凡
Owner XINJIANG HUASHIDAN PHARMA RES
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