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Propionylation catalpol derivative and preparation method and application thereof

A technology of derivatives and propionylation, which is applied in the preparation of sugar derivatives, sugar derivatives, sugar derivatives, etc., can solve the problems of restricting the clinical application of catalpol, low fat solubility and low distribution of catalpol, and improve blood Brain barrier permeability, good anti-aging activity, high bioavailability effect

Pending Publication Date: 2018-02-27
HENAN UNIV OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

As a small molecule drug, catalpol has high water solubility and is easy to take orally, but Wan GQ et al. .Journal of Pharmaceutical and Biomedical Analysis, 2012, 70:337-343) Studies have shown that catalpol has low fat solubility, is not easy to pass through the blood-brain barrier, and is not highly distributed in the brain, which restricts catalpol as an anti-aging drug clinical application

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  • Propionylation catalpol derivative and preparation method and application thereof
  • Propionylation catalpol derivative and preparation method and application thereof
  • Propionylation catalpol derivative and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0046] A propionylated catalpol derivative obtained by esterification of catalpol and propionic anhydride. During esterification, 6 hydroxyl groups or 1 to 5 hydroxyl groups of catalpol participate in the esterification reaction.

[0047] The preparation method of propionylated catalpol derivatives, comprises the following steps:

[0048] 1) Dissolve 100 mg (0.27 mmol) catalpol in 5 mL of pyridine, add 424.57 μL (3.25 mmol) of propionic anhydride, and react at 60° C. for 48 h. The liquid phase monitoring reaction ends, and the mass spectrometry detects that the esterification yield is 96.71 %, evaporate the pyridine to dryness to obtain the product;

[0049] 2) The product of step 1) was dissolved in 40 mL of ethyl acetate, then 40 mL of saturated sodium carbonate solution was added, the layers were allowed to stand, and the lower aqueous phase was discarded (the saturated sodium carbonate solution was added, and the layers were left to stand, and the lower aqueous phase was ...

Embodiment 2

[0053] A propionylated catalpol derivative obtained by esterification of catalpol and propionic anhydride. During esterification, part of the hydroxyl groups of catalpol participates in the esterification reaction.

[0054] The preparation method of propionylated catalpol derivatives, comprises the following steps:

[0055] 1) Dissolve 0.27 mmol catalpol in 6.5 mL pyridine, add 1.63 mmol propionic anhydride, react at 30° C. for 24 h, and evaporate pyridine to dryness to obtain the product;

[0056] 2) Dissolve the product of step 1) in 30 mL of ethyl acetate, add 20 mL of saturated sodium carbonate solution, leave to stand for stratification, discard the lower aqueous phase (add saturated sodium carbonate solution, leave to stand for stratification, discard the lower aqueous phase, this The steps were repeated 3 times), the organic phase was dried to remove water using anhydrous sodium sulfate, evaporated to dryness ethyl acetate, column chromatography, evaporated to dryness ...

Embodiment 3

[0059] A propionylated catalpol derivative obtained by esterification of catalpol and propionic anhydride. During esterification, part of the hydroxyl groups of catalpol participates in the esterification reaction.

[0060] The preparation method of propionylated catalpol derivatives, comprises the following steps:

[0061] 1) Dissolve 0.27 mmol catalpol in 4 mL pyridine, add 2.43 mmol propionic anhydride, react at 90°C for 12 h, evaporate the pyridine to dryness to obtain the product;

[0062] 2) Dissolve the product of step 1) in 40 mL of ethyl acetate, add 40 mL of saturated sodium carbonate solution, leave to stand for stratification, discard the lower aqueous phase (add saturated sodium carbonate solution, leave to stand for stratification, discard the lower aqueous phase, this The steps were repeated 3 times), the organic phase was dried to remove water using anhydrous sodium sulfate, evaporated to dryness ethyl acetate, column chromatography, evaporated to dryness of t...

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Abstract

The invention discloses a propionylation catalpol derivative, which is prepared by esterifying catalpol and propionic anhydride and also provides a corresponding preparation method and application thereof. According to the propionylation catalpol derivative disclosed by the invention, the propionic anhydride and the catalpol are subjected to esterification reaction to generate an esterification product from the esterification reaction in which all six hydroxyls or 1 to 5 hydroxyls of the catalpol partially participate, and namely, the esterification product is the full-propionylation or partial-propionylation catalpol derivative. The catalpol derivative has good anti-aging activity, blood-brain barrier permeability of the catalpol is improved, and an esterification yield can reach 96.71%;ideas are provided for researching action modes and anti-ageing action mechanisms of the catalpol derivative and target protein, reference is provided for further synthesizing anti-aging medicine withhigher activity and higher bioavailability, and later development of catalpol is facilitated.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry and medicine, and in particular relates to a propionylated catalpol derivative and a preparation method and application thereof. Background technique [0002] Aging usually refers to a series of systemic and multi-faceted degenerative changes that inevitably occur in the form, structure and physiological function of the human body after its growth and development reaches the mature stage, such as skin atrophy and bone loss. , atherosclerosis, senile dementia, etc. With the intensification of the global aging trend, researchers from various countries have made significant progress in many aspects such as longevity mechanism, epigenetic regulation of aging, metabolism and aging, etc. The research on anti-aging drugs has become a hot spot in the current field of geriatrics. Traditional Chinese medicine, with its unique curative effect, occupies an increasingly important position in anti-...

Claims

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Application Information

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IPC IPC(8): C07H17/04C07H1/00A61P39/06A61P39/00
CPCC07H1/00C07H17/04
Inventor 董春红王强王国庆褚铭林朱伟明
Owner HENAN UNIV OF CHINESE MEDICINE
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