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Betulinic acid derivative as well as preparation method, pharmaceutical composition and application thereof

A technology of betulinic acid and its derivatives, applied in the field of medicine, can solve the problems of low bioavailability, in vivo transmission, metabolism, and poor solubility, and achieve excellent anti-tumor activity, high yield, and good application value

Pending Publication Date: 2022-01-11
河南省生殖健康科学技术研究院 +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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  • Betulinic acid derivative as well as preparation method, pharmaceutical composition and application thereof
  • Betulinic acid derivative as well as preparation method, pharmaceutical composition and application thereof
  • Betulinic acid derivative as well as preparation method, pharmaceutical composition and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0085] Embodiment 1: the preparation of compound

[0086] Preparation of compound ZX-6 adopts the following method:

[0087] a. First use Jones reagent to oxidize betulinic acid to betulinic acid compound 2.

[0088] b. Using oxalyl chloride and methanol to esterify the betulinic acid compound 2 prepared in step a) into betulinic acid methyl ester compound 3.

[0089] c. using propyne bromide to react with betulinate methyl ketoate compound 3 prepared in step b) to obtain compound 4.

[0090] d. Using sodium borohydride to reduce the carbonyl group in compound 4 prepared in step c) to hydroxyl to prepare compound 5.

[0091] e. using lithium iodide to demethylate the compound 5 prepared in step d) into a carboxylic acid, and prepare compound 6.

[0092] f. Adding 4'-azacytidine to the betulinic acid compound 6 prepared in step e) through a click reaction to synthesize the betulinic acid derivative ZX-6.

[0093]

[0094] Concrete synthetic route is as follows:

[0095]...

Embodiment 2

[0105] Embodiment 2: biological activity test

[0106] 2.1 The inhibitory activity test of the compound of the present invention to Hela, C33a, Siha cells

[0107] In this experiment, different concentrations of test compounds were used to act on human cervical cancer cell lines Hela, C33a, and Siha cells for 48 hours, and the inhibition rate of cell growth was detected by MTT method to detect the inhibition degree of compounds on different tumor cells.

[0108] experimental method:

[0109] Dissolve the subject in a certain volume of DMSO, make a mother solution with a concentration of 10mmol / L and store it at 4°C. When used, take the mother solution and dilute it to a certain multiple solution.

[0110] The specific operation steps are as follows:

[0111] (1) Take Hela, C33a, and Siha cells in the logarithmic growth phase, centrifuge, resuspend, and adjust the cell suspension density to 8×10 4 cell / mL, inoculate in 96-well culture plate, add 100 μL of cell suspension to ...

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Abstract

The invention belongs to the field of medicines, and particularly provides a betulinic acid derivative as shown in a formula (I), and pharmaceutically acceptable salts, hydrates or prodrugs thereof. The invention also provides a pharmaceutical composition, a synthetic method and application of the betulinic acid derivative.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to a betulinic acid derivative, a preparation method, a pharmaceutical composition and an application thereof. 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-virus, anti-tumor, and anti-inflammatory effects. Compared with betulinic acid, its derivatives have better anti-tumor activity. For example, RPR103611 and PA457 (bevirimat) are already in anti-HIV clinical trials, and NVX-207 is in anti-tumor clinical trials. 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] In order to improve the above technical problems, the present invention provides a b...

Claims

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Application Information

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IPC IPC(8): C07J63/00A61K31/56A61P35/00
CPCC07J63/008A61P35/00
Inventor 王强王艳丽张军喜郑立运张超楠祁少可位婷婷王卓王晓慧王明升李向力张豫黎
Owner 河南省生殖健康科学技术研究院
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