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Betulin keto acid derivatives and their synthesis method and application

A technology of betulinic acid and betulinic acid, which is applied in the fields of medicine and its preparation and application, can solve the problems of low bioavailability in vivo transmission, metabolism, poor solubility, etc., achieve good application value, make up for poor water solubility and low toxicity Effect

Active Publication Date: 2019-06-07
HIGH & NEW TECH RES CENT OF HENAN ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to its poor solubility in water, it leads to low bioavailability and shortcomings in in vivo transmission and metabolism.

Method used

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  • Betulin keto acid derivatives and their synthesis method and application
  • Betulin keto acid derivatives and their synthesis method and application
  • Betulin keto acid derivatives and their synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] The synthesis of embodiment 1 compound iv

[0032] The synthesis path is as follows:

[0033]

[0034] in

[0035] Synthesis of Compound 2: Add betulin (20.0 g, 45.2 mmol) and acetone (400 mL) into a 1000 mL three-necked flask, then add the newly prepared Jones reagent (100 mL) dropwise under ice bath, and continue the reaction for 30 Minutes later, remove the ice bath, stir at room temperature for 8 hours, add methanol (250mL) and water (250mL) to terminate the reaction, evaporate the solvent, add water, extract with ethyl acetate, combine the organic phases, dry and concentrate, and separate by column chromatography to obtain a white solid 2 (12.2 g, 26.8 mmol, 59.3%). 1 HNMR (DMSO-d 6 ,400MHz) δ: 12.08(s,1H),4.70(s,1H),4.57(s,1H),2.90~2.99(m,1H),2.46~2.30(m,2H),2.25(dt,J= 12.7, 3.5Hz, 1H), 2.15~2.08(m, 1H), 1.87~1.73(m, 3H), 1.65(s, 3H), 1.62(s, 1H), 1.54(t, J=11.3Hz, 1H ),1.48~1.00(m,15H),0.98(s,3H),0.95(s,3H),0.93(s,3H),0.90(s,3H),0.85(s,3H).

[0036] Sy...

Embodiment 2

[0039] The synthesis of embodiment 2 compound ii

[0040] The synthesis path is as follows:

[0041]

[0042] Synthesis of Compound 2: Add betulin (20.0g, 45.2mmol) and acetone (400mL) to a 1000mL three-neck flask, then add the newly prepared Jones reagent (100mL) dropwise under ice bath, and continue the reaction for 30 Minutes later, remove the ice bath, stir at room temperature for 8 h, add methanol (250 mL) and water (250 mL) to terminate the reaction, evaporate the solvent to dryness, add water, extract with ethyl acetate, combine the organic phases, dry and concentrate, and separate by column chromatography to obtain a white solid 2 (12.2 g, 26.8 mmol, 59.3%). 1 HNMR (DMSO-d 6 ,400MHz) δ: 12.08(s,1H),4.70(s,1H),4.57(s,1H),2.90~2.99(m,1H),2.46~2.30(m,2H),2.25(dt,J= 12.7, 3.5Hz, 1H), 2.15~2.08(m, 1H), 1.87~1.73(m, 3H), 1.65(s, 3H), 1.62(s, 1H), 1.54(t, J=11.3Hz, 1H ),1.48~1.00(m,15H),0.98(s,3H),0.95(s,3H),0.93(s,3H),0.90(s,3H),0.85(s,3H).

[0043] Synthesis of Comp...

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Abstract

The invention discloses a betulinic acid derivative shown as a formula (I) and a synthesis method and the application thereof. The betulinic acid derivative contains a betulinic acid part which is covalently bounded to a linker 1,2,3-triazole at C-2 of the betulinic acid part, and the linker is covalently bounded to a 2'-fluoro-aabinonucleoside part. The compound provided by the invention solves the problem of low water solubility of betulinic acid by chemical method design; the betulinic acid is linked to a nucleoside compound through the stable 1,2,3-triazole linker.

Description

technical field [0001] The invention belongs to the technical field of medicine and its preparation and application, and in particular relates to a betulin keto acid derivative and its synthesis method and application. Background technique [0002] Betulinic acid (BA) is a pentacyclic triterpenoid compound that exists in many plants such as birch, Prunella vulgaris, and papaya. Studies have found that betulinic acid has a wide range of physiological activities, such as anti-HIV, anti-tumor, and anti-inflammatory effects. Compared with betulinic acid, its derivatives have better activity in anti-HIV, anti-tumor, etc. For example, RPR103611 and PA457 (bevirimat) are in the clinical trial stage of anti-HIV, and NVX-207 is in the clinical trial of anti-tumor . However, due to its poor solubility in water, it leads to low bioavailability and shortcomings in in vivo transportation and metabolism. Contents of the invention [0003] The main purpose of the present invention is ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J63/00A61P35/00A61P31/12A61P31/18A61P31/20
CPCA61P31/12A61P31/18A61P31/20A61P35/00C07J63/008
Inventor 李玉江王强郑立运郝佳唐雪峰张豫黎刘陆平方先珍郭晓河陶乐黄小婉郑果董黎红余学军
Owner HIGH & NEW TECH RES CENT OF HENAN ACAD OF SCI
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