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

Rosinyl diterpene modified alpha - phosphoramidate, preparation method, and application for anti tumors

A technology of rosin-based tricyclic diterpene and amino phosphonate, which is applied in the fields of antineoplastic drugs, chemical instruments and methods, and pharmaceutical formulations to achieve high antitumor activity, low toxicity, and improved fat solubility

Inactive Publication Date: 2007-07-25
JIANGSU QIANGLIN BIO ENERGY
View PDF0 Cites 19 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

(Document 1: Feio S.S.; Giganteb, C.R.; Marcelo-Curto M.J.Method on multiwell plates for the evaluation of the antimicrobial activity of resin acid derivatives [J], J.of Microbio.Methods.1997, 28, 201-206; Document 2 : Hu Deyu, Song Baoan, Zhang Guoping, et al. Synthesis and crystal structure of O, O′-di-n-butyl-α-(4-trifluoromethylanilino)-2-fluorophenylphosphonate under ultrasonic irradiation[ J], Organic Chemistry, 2005, 25 (7), 854-858.) People try to use various synthetic methods to prepare N-terminal (nitrogen terminal), C-terminal (carbon terminal) and P-terminal (phosphorus terminal) It is a new derivative of amino phosphonate with different substituents in order to find compounds with high biological activity. The N-terminal introduction of tricyclic diterpene and groups with multiple chiral centers has not been reported in the literature

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
  • Rosinyl diterpene modified alpha - phosphoramidate, preparation method, and application for anti tumors
  • Rosinyl diterpene modified alpha - phosphoramidate, preparation method, and application for anti tumors
  • Rosinyl diterpene modified alpha - phosphoramidate, preparation method, and application for anti tumors

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] A kind of α-aminophosphonate modified by rosin-based tricyclic diterpene, its general structural formula is as follows:

[0028]

[0029] Among them, R 1 One of the following substituents:

[0030]

[0031] Dehydroabietyl, abietyl, dihydroabietyl, tetrahydroabietyl,

[0032]

[0033] Degrade dehydroabietyl, degrade abietyl, degrade dihydroabietyl, degrade tetrahydroabietyl,

[0034] R 2 is one of the following groups:

[0035] Me (methyl), Et (ethyl), n-Pr (n-propyl), i-Pr (isopropyl), Bu (butyl), Ph (phenyl);

[0036] R 3 The substitution position is the meta, right, ortho position of the corresponding position on the benzene ring of the externally connected long-chain group, R 3 The represented substituent is one of the following groups or group combinations,

[0037] i.e. R 3 Can be one of the following groups:

[0038] H (hydrogen), o-F (o-fluorine), m-F (m-fluorine), p-F (p-fluorine), p-Cl (p-chlorine), p-CF 3 (p-trifluoromethyl), p-OMe (p-methox...

Embodiment 2

[0042]The preparation method of the α-amino phosphonate of above-mentioned abietyl tricyclic diterpene modification is, with abietyl diterpene amine (as dehydroabietyl, aietyl, dihydroabietyl, tetrahydroabietyl, degradation dehydrogenation Abietyl, degraded aietyl, degraded dihydroabietyl, degraded tetrahydroabietyl), substituted benzaldehyde and phosphite are raw materials to synthesize rosin-based tricyclic diterpene-modified α-aminophosphonate, and the synthesis method is solvent Synthesis method or one-pot synthesis method or solvent-free synthesis method, wherein the ratio of the amount of rosin-based diterpene amine to substituted benzaldehyde and phosphite is 1: (1-1.05): (1-1.1), such as Selected as: 1:1.01:1, 1:1.02:1, 1:1.03:1, 1:1.04:1, 1:1.05:1, 1:1.01:1.01, 1:1.01:1.02, 1:1.01 : 1.03, 1: 1.01: 1.04, 1: 1.01: 1.05, 1: 1.01: 1.06, 1: 1.01: 1.07, 1: 1.01: 1.09, 1: 1.02: 1.01, 1: 1.02: 1.03, 1: 1.02: 1.05 , 1:1.02:1.06, 1:1.02:1.06, 1:1.02:1.09, 1:1.02:1.1, 1:1.03:1....

Embodiment 3

[0053] An abietyl tricyclic diterpene-modified α-aminophosphonate for anti-tumor application, which uses the above-mentioned rosin-based tricyclic diterpene-modified α-aminophosphonate as an active ingredient.

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

This invention relates to a method for preparing roinyl diterpene modified alpha-aminophosphate, and its anti-tumor application. The method comprises: reacting roinyl amine diterpenoid with substituted benzaldehyde and phosphite at a mol ratio of 1 :( 1-1.05) :( 1-1.1) by solvent synthesis, one-pot synthesis or solvent-free synthesis. The inroduction of roinyl diterpene into aminophosphate can largely improve the liposolubility and bioactivity of the compound. R1 structure comes from natural product rosin, thus has low toxicity.

Description

technical field [0001] The invention relates to a derivative of rosin resin acid compound, a preparation method and its application as a medicine, in particular to a rosin-based diterpene modified α-phosphoramidate, a preparation method and an antitumor application. Background technique [0002] Amino phosphonates, as phosphorous analogs of amino acid esters, have a wide range of herbicidal, bactericidal and plant growth regulating activities. Certain amino phosphonates also have biological activities such as anticancer and antitumor and are used as starting materials to synthesize a series of Phosphopeptides. Therefore, research on the synthesis and biological activity of aminophosphonate derivatives has aroused widespread interest. (Document 1: Feio S.S.; Giganteb, C.R.; Marcelo-Curto M.J.Method on multiwell plates for the evaluation of the antimicrobial activity of resin acid derivatives [J], J.of Microbio.Methods.1997, 28, 201-206; Document 2 : Hu Deyu, Song Baoan, Zha...

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): C07F9/40A61K31/662A61P35/00
Inventor 宋湛谦饶小平商士斌高宏姚绪杰
Owner JIANGSU QIANGLIN BIO ENERGY
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