6- methylcoumarin-7-sulfonylurea compound and synthetic method thereof

A technology of methyl coumarin and sulfonylurea, which is applied in the directions of organic chemistry, drug combination, metabolic diseases, etc., to achieve the effect of simple and easy synthesis method

Inactive Publication Date: 2010-02-10
祁刚
View PDF0 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Literature [Han Ying, Tu Shuzi, Zhou Weifen, et al. Synthesis of coumarin sulfonylureas and their hypoglycemic activity[J], Journal of China Pharmaceutical University, 2002, 33(2): 93-97; Qi Gang , Tu Shuzi, Wang Qiujuan. Synthesis and hypoglycemic activity of 3-bromocoumarin sulfonylurea compounds[J], Journal of China Pharmaceutical University, 2005, 36(1):7-9; , combining coumarin with the pharmacophore sulfonylurea group in sulfonylurea hypoglycemic compounds to obtain a series of compounds, but in the current published literature, the substitution position of the sulfonylurea group is all substituted at the 6-position

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
  • 6- methylcoumarin-7-sulfonylurea compound and synthetic method thereof
  • 6- methylcoumarin-7-sulfonylurea compound and synthetic method thereof
  • 6- methylcoumarin-7-sulfonylurea compound and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1: 6-methylcoumarinsulfonyl chloride (2)

[0029] Add 10 g of 6-methylcoumarin (1) (0.06 mol) to 9 mL of chlorosulfonic acid (0.15 mol) in an ice-water bath, keep the temperature below 10 ° C, after the addition is complete, stir at room temperature until the solid is completely dissolved, and then Heat to 90-95°C to continue the reaction for 4h, cool to room temperature, pour into 20g of crushed ice under vigorous stirring (800r / min), filter with suction to obtain a solid, wash twice with water to obtain crude 6-methylcoumarinsulfonyl chloride ( 2) 16g is directly used in the next step reaction.

Embodiment 2

[0030] Embodiment 2: 6-methylcoumarin sulfonamide (3)

[0031] Add 16 g of the obtained 6-methylcoumarin sulfonyl chloride crude product (2) to 15 mL of 28% concentrated ammonia water cooled by ice water, stir at room temperature for 8 h, adjust the pH to neutral with dilute hydrochloric acid, and recrystallize from water to obtain 2.30 g of white powder that is It is 6-methylcoumarin sulfonamide (3), the yield is 16%, mp.245~247℃. ESI-MS: 262[M+Na] +

Embodiment 3

[0032] Embodiment 3: the synthetic general method of isocyanate

[0033] Dissolve 12g of triphosgene (0.40mol) in 50mL of chloroform, stir and dissolve, then add dropwise 10mL of the chloroform solution of the corresponding amine compound (0.02moL) under ice bath cooling, the amine compound described here is 2-methylaniline , 3-methylaniline, 4-methylaniline, 2,3-dimethylaniline, benzylamine or n-propylamine, after addition, react at room temperature for 1h, then heat to reflux for 6h, and distill to obtain the corresponding isocyanate.

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 6-methylcoumarin-7-sulfonylurea compound with the following structural formula and a synthetic method of the compound. Proofed by an initial pharmacological test, the hypoglycemic activity of the 6-methylcoumarin-7-sulfonylurea compound is similar to 6-bit substitution, and the 6-methylcoumarin-7-sulfonylurea compound can be used as a substitution product of a coumarin-6-sulfonylurea compound. The synthetic method of the 6-methylcoumarin-7-sulfonylurea compound is easy and has an industrialization prospect.

Description

technical field [0001] The invention relates to 6-methylcoumarin-7-sulfonylurea compounds and a synthesis method thereof. Background technique [0002] Diabetes mellitus is a chronic disease caused by genetic or acquired insufficient insulin secretion by the pancreas or insulin resistance. Its complications include cardiovascular disease, renal failure, retinopathy, foot ulcers, infection and nervous system disorders. The natural compound coumarin (I) and its derivatives are widely distributed in the plant kingdom and have various physiological activities, such as anti-infection, anti-virus, anti-cancer and anti-coagulation. Oral administration of 250 mg / kg has a significant hypoglycemic effect on normal and alloxan diabetic rats. Sulfonylureas are one of the earliest oral hypoglycemic drugs, and their mechanism of action is to stimulate β cells to secrete insulin. The representative drug is glimepiride. Literature [Han Ying, Tu Shuzi, Zhou Weifen, et al. Synthesis of coum...

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 Applications(China)
IPC IPC(8): C07D311/16A61P3/10
Inventor 祁刚
Owner 祁刚
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap