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

Alpha-glucosidase inhibitor, and synthesis method and application thereof

A technology of glucosidase and synthesis method, which is applied in the field of α-glucosidase inhibitor and its synthesis, and achieves the effects of good inhibitory activity and good application prospect

Pending Publication Date: 2019-12-03
WUYI UNIV +1
View PDF0 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the α-glucosidase inhibitors currently used clinically (acarbose, voglibose and miglitol) all have adverse reactions of varying degrees, such as abdominal distension, borborygmus, abdominal pain, and diarrhea.

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
  • Alpha-glucosidase inhibitor, and synthesis method and application thereof
  • Alpha-glucosidase inhibitor, and synthesis method and application thereof
  • Alpha-glucosidase inhibitor, and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Synthesis of 1,2,4,5-tetramethoxybenzene (Intermediate A)

[0050]

[0051]2,5 dihydroxy-1,4 benzoquinone (5 g, 3.6 mmol) was dissolved in 200 mL methanol solution, 38% concentrated hydrochloric acid (6 mL, 72.0 mmol) was added slowly, and stirred overnight at room temperature. After the reaction was completed (TLC), suction filtration and concentration gave a yellow solid intermediate product 1; the obtained intermediate product 1 was dissolved in 50 mL of water, sodium dithionite (10 g, 57.4 mmol) was added, and the reaction was refluxed for 8 minutes at 120 ° C. Cooling and crystallization at 4°C, the mixture was suction filtered to obtain powdery white crystalline intermediate 2 (4.5g, 73.5%); intermediate 2 (1.7g, 10mmol) was dissolved in 10mLDMSO, and potassium hydroxide (1.4g, 25mmol), stirred at room temperature for 15 minutes, added dropwise methyl iodide (1.88mL, 25mmol), and reacted overnight. The end point of the reaction was detected by TLC (developing ...

Embodiment 2

[0054] Synthesis of 1,2,4,5-tetramethoxy-3-(7-phenylheptyl)-benzene (intermediate B1)

[0055]

[0056] Add intermediate A (1 g, 5.1 mmol) into a round-bottomed flask, dry it in vacuum for 30 minutes, add HMPA (353 μL, 2 mmol), ventilate 2 to 5 times, and then add 60 mL of tetrahydrofuran as a solvent. React in anaerobic water for 15 minutes, slowly add n-butyllithium (2.44mL, 6.12mmol), adjust the temperature to -10°C for 1 hour, add 1-bromo-7-phenylheptane dropwise, and continue the reaction for 10 minutes . Then the mixture was reacted at room temperature for 10 hours. After concentrating the reaction liquid under reduced pressure, dissolve it with an organic solvent, adjust the pH to 5-6 with a saturated ammonium chloride solution, wash the organic phase with distilled water and saturated brine respectively, collect the organic phase and dry it with anhydrous magnesium sulfate, filter, and decompress Concentrate to obtain the crude product, which is purified by silica...

Embodiment 3

[0066] Synthesis of 1,2,4,5-tetramethoxy 3-(2-cyclohexylethyl)benzene (intermediate B2)

[0067]

[0068] Add intermediate A (1 g, 5.1 mmol) into a round-bottomed flask, dry it in vacuum for 30 minutes, add HMPA (353 μL, 2 mmol), ventilate 2 to 5 times, and then add 60 mL of tetrahydrofuran as a solvent. Water was reacted without oxygen for 15 minutes, n-butyllithium (2.44 mL, 6.12 mmol) was slowly added, the temperature was adjusted to -10°C for 1 hour, 2-bromoethylcyclohexane was added dropwise, and the reaction was continued for 10 minutes. Then the mixture was reacted at room temperature for 10 hours. After concentrating the reaction liquid under reduced pressure, dissolve it with an organic solvent, adjust the pH to 5-6 with a saturated ammonium chloride solution, wash the organic phase with distilled water and saturated brine respectively, collect the organic phase and dry it with anhydrous magnesium sulfate, filter, and decompress Concentrate to obtain crude product...

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 an alpha-glucosidase inhibitor, and a synthesis method and application thereof. The invention aims to provide the alpha-glucosidase inhibitor with a relatively good hypoglycemic effect. The structural formula of the alpha-glucosidase inhibitor is shown in the specification, wherein R1 is selected from H or CH3, and R2 is selected from the groups shown in the specification.The invention belongs to the technical field of medicines.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to an α-glucosidase inhibitor and its synthesis method and application. Background technique [0002] According to the report of the International Diabetes Organization, the number of diabetic patients in the world will reach 552 million in 2030, and it has become the third chronic disease that seriously threatens human life and health after tumors and cardiovascular and cerebrovascular diseases. This has led to an increase in healthcare spending and related social problems. The most frightening thing about diabetes is its complications. Its incidence ranges widely, covering almost every tissue and organ in the body. It has a long course of disease, is difficult to cure, and has a very high rate of death and disability. [0003] According to different pathogenesis, diabetes is divided into type I diabetes (insulin-dependent), type II diabetes (non-insulin dependent) an...

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): C07C50/28C07C46/00A61P3/04A61P3/10A61K31/122A23L33/10
CPCC07C50/28A61P3/04A61P3/10A61K31/122A23L33/10C07C2601/16C07C2601/14A23V2002/00A23V2200/328A23V2200/332A23V2250/30
Inventor 盛钊君陈小乐简荣超唐小文李钰铃吴盼盼张焜
Owner WUYI 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