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

Phosphine isocoumarin amide, synthesis and uses thereof

An isocoumarin amide and reaction technology, which is applied in the field of phosphinocoumarin amide compounds and their synthesis, can solve the problems affecting the biological activity research of such compounds, and achieve a simple and efficient synthesis method, good cholesterol esterase, inhibit cholesterol The effect of esterase

Inactive Publication Date: 2011-06-01
SUN YAT SEN UNIV
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The backwardness of synthetic methods has seriously affected the research on the biological activity of such 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
  • Phosphine isocoumarin amide, synthesis and uses thereof
  • Phosphine isocoumarin amide, synthesis and uses thereof
  • Phosphine isocoumarin amide, synthesis and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026]

[0027] Typical operation of DIBAL-H as a metal reagent: under nitrogen protection, add PhCH to a 50mL dry round bottom flask 2 NH 2 (0.96mL, 8.8mmol), toluene (5.0mL), under an ice-water bath, slowly add 1M DIBAL-H toluene solution (8.80mL, 8.8mmol) dropwise, and continue to react at 0°C for 1 hour after the drop.

[0028] Slowly add 3-phenyl-7-methoxyphosphine isocoumarin ethyl ester (475mg, 1.5mmol) in toluene (5.0mL) dropwise to the above reaction solution, after the dropwise addition, naturally rise to room temperature and react for 12 hours, The reaction solution was cooled to 0°C, washed with water (10mL), 1M KHSO 4 Wash with aqueous solution, extract with ethyl acetate (3×10 mL), dry over anhydrous sodium sulfate, filter, evaporate the solvent under reduced pressure, and obtain 370 mg of white solid by column chromatography (P:E=6:1-1:1) of the residue. For the corresponding phosphine isocoumarinamide, the yield is 65%. 1 H NMR: δ7.72(d, J=7.5Hz, 2H), 7.2...

Embodiment 2

[0030]

[0031] Typical operation of n-butyllithium (n-BuLi) as a metal reagent: under nitrogen protection, in a 50mL dry round bottom flask, add cyclohexylamine (0.27mL, 2.5mmol), anhydrous 1,4-dioxane ( 5.0 mL), slowly dropwise added 1.6M n-butyllithium n-hexane solution (1.30 mL, 2.1 mmol) at -15°C, and continued to react at -15°C for 1 hour after the drop was completed.

[0032] Slowly add 3-phenylphosphineisocoumarin ethyl ester (286mg, 1.0mmol) in anhydrous 1,4-dioxane (5.0mL) dropwise to the above reaction solution, after the dropwise addition, warm to 0°C for reaction After 2 hours, water (10 mL) was added, extracted with ethyl acetate (3×10 mL), dried over anhydrous sodium sulfate, filtered, the solvent was evaporated under reduced pressure, and the residue was subjected to column chromatography (P:E=6:1-1: 1) 237 mg of white solid was obtained, which was the corresponding phosphine isocoumarinamide, and the yield was 70%. 1 H NMR: δ7.29-7.52(m, 9H), 6.52(s, 1H), ...

Embodiment 3

[0034]

[0035] Typical operation of sodium hydride (NaH) as a metal reagent: under nitrogen protection, add 60% NaH powder (264mg, 6.6mmol) and anhydrous tetrahydrofuran (THF, 5.0mL) into a 50mL dry round bottom flask, slowly Add nBuNH dropwise 2 (0.50mL, 5.0mmol), warmed up to room temperature to react for 1 hour after dropping.

[0036] Slowly add a solution of 3-phenyl-7-chlorophosphineisocoumarin ethyl ester (320mg, 1.0mmol) in anhydrous THF (5.0mL) dropwise to the above reaction solution at room temperature. After the dropwise addition, raise the temperature to 60°C for 3 hours , cooled to room temperature, added water (10mL), extracted with ethyl acetate (3×10mL), dried over anhydrous sodium sulfate, filtered, evaporated the solvent under reduced pressure, and the residue was subjected to column chromatography (P:E=6:1-1 : 1) 209 mg of white solid was obtained, which was the corresponding phosphine isocoumarin amide, and the yield was 60%. 1 H NMR: δ7.76-7.89(m, 3H),...

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 present invention relates to a novel phosphonic isocoumarin amide and a preparation method and an application thereof. The phosphonic isocoumarin amide has a formula B; wherein, R<1> represents H, C1-C10 alkyl, C3-C7 naphthenic bases, aryl, or C1-C10 alkyl, C3-C7 naphthenic bases and substitutive derivatives of the aryl; R<2> and R<3> respectively independently represent H, C1-C10 alkyl, C1-C5 alkoxyl, C3-C7 naphthenic bases, aryl, or C1-C10 alkyl, C3-C7 naphthenic bases and substitutive derivatives of the aryl group; X represents H, halogen, aryl and aryl-ethynyl; and Y represents H, C1-C5 alkyl, C1-C5 alkoxyl, carbonyl, halogen, CN, CF3, NO2, OH or amino. The phosphonic isocoumarin amide described by the present invention has a good function of inhibiting cholesterol esterase and can provide a new option for the preparation of drugs treating diseases such as hyperlipoidemia.

Description

technical field [0001] The invention relates to a phosphine isocoumarin amide compound and its synthesis method and application. Background technique [0002] Organophosphorus compounds are closely related to life chemistry and have a wide range of applications in the fields of pesticides and medicine. In today's pharmaceutical industry, organophosphorus drugs not only occupy an important position in antineoplastic drugs, but also play an important role in the fields of antibacterial, antiviral, cardiotonic, antihypertensive, enzyme inhibitors, and treatment of orthopedic diseases (Engel, R ., Ed. Handbook of Organophosphorus Chemistry; Marcel Dekker: New York, 1992, Chapter 11; Quin, L.D., Ed. A Guide to Organophosphorus Chemistry; John Wiley & Sons: New York, 2000, Chapter 11). How to find new organic phosphorus compounds with biological activity has become one of the key topics in the research of organophosphorus chemistry. [0003] In the previous work of the inventor,...

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): C07F9/6571A61K31/665A61P3/06
Inventor 彭爱云郭御卷王正李保健杜一丹
Owner SUN YAT SEN 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