Oridonin A Schiff base derivative and its preparation method and application

A technology of oridonin A and Schiff base, applied in the field of medicine, can solve the problems of low blood drug concentration, poor anti-tumor effect, toxic and side effects, etc.

Active Publication Date: 2019-01-08
江苏泓诺健生物医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

After oral administration of tablets and syrups, the blood concentration is low and the antitumor effect is poor
Injections mainly use organic solvents and surfactants to increase the solubility of oridonin, but long-term use will cause a large number of toxic and side effects

Method used

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  • Oridonin A Schiff base derivative and its preparation method and application
  • Oridonin A Schiff base derivative and its preparation method and application
  • Oridonin A Schiff base derivative and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Preparation of Oridonine A Lysine Schiff Base (1)

[0025] The structure of compound (1) is shown in the following formula:

[0026]

[0027] Take 546mg (1mmol) L-Fmoc-Lys (Dde)-OCH 3 Add 10 mL of CH containing 2% hydrazine hydrate 2 Cl 2 , stirred for 30 minutes, washed with saturated brine, added equimolar oridonin, refluxed for 12 hours, cooled, filtered, and concentrated to obtain a solid with a yield of 87%.

[0028] The obtained solid was added to 20% piperidine DMF solution, stirred at room temperature for 3 hours, then added 2mol / L NaOH solution for hydrolysis, adjusted to pH 5-7 with dilute hydrochloric acid, evaporated to dryness under reduced pressure, and purified to obtain compound (1) with a yield of 78%. MS (ESI) m / z:537.3 [M] + .

Embodiment 2

[0030] Preparation of Oridonine A Lysine-Alanine Schiff Base (2)

[0031] The structure of compound (2) is shown in the following formula:

[0032]

[0033] Referring to Example 1, get 717mg (1mmol) L-Fmoc-Lys (Dde)-Ala-OCH 3 Instead of 546mg (1mmol) L-Fmoc-Lys (Dde)-OCH 3 , Compound (2) was obtained in a yield of 76%. MS (ESI) m / z:608.4 [M] + .

Embodiment 3

[0035] Preparation of Oridonine A Lysine-Phenylalanine Schiff Base (3)

[0036] The structure of compound (3) is shown in the following formula:

[0037]

[0038] Referring to Example 1, get 793mg (1mmol) L-Fmoc-Lys (Dde)-Phe-OCH 3 Instead of 546mg (1mmol) L-Fmoc-Lys (Dde)-OCH 3 , Compound (3) was obtained in a yield of 77%. MS (ESI) m / z:684.4 [M] + .

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Abstract

The invention relates to an oridonin Schiff base derivative. The invention also discloses a preparation method of the oridonin Schiff base derivatives and uses of the compounds in tumor resistance.

Description

technical field [0001] The invention relates to a Schiff base derivative of oridonin A, a preparation method and application thereof, and belongs to the field of medicines. Background technique [0002] Oridonin is a natural organic compound of kaurene diterpenes, which has the functions of clearing heat and detoxifying, promoting blood circulation and removing blood stasis, antibacterial and anti-inflammatory, and antitumor. But Rubescensine A is insoluble in water, and its preparations are mainly tablets, syrups and injections. After oral administration of tablets and syrups, the blood drug concentration is low and the antitumor effect is poor. Injections mainly use organic solvents plus surfactants to increase the solubility of oridonin, but long-term use will cause a large number of toxic and side effects. In the present invention, the carbonyl of oridonin is modified with lysine and a peptide containing lysine to form an imine bond, which can improve the solubility of...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/10A61P35/00A61P31/04A61P29/00
CPCC07D493/10
Inventor 史兰香张宝华刘斯婕郭瑞霞
Owner 江苏泓诺健生物医药科技有限公司
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