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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
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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

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  • 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

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Experimental program
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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.

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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

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Application Information

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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
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