Croton acylated catapol derivative as well as preparation method and application thereof

A crotonylation and derivative technology, applied in the field of crotonylated catalpol derivatives and their preparation, can solve problems such as catalpol anhydride esterification derivatives that have not been found, achieve good anti-aging activity, improve blood-brain barrier The effect of permeability and high bioavailability

Active Publication Date: 2018-11-30
HENAN UNIV OF CHINESE MEDICINE
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

After consulting the literature, so far, except that Carlos C R et al. (Novel antiproliferative analogs of the Taq DNA polymerase inhibitor catalpol [J]. Bioorganic & Medicinal Chemis

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  • Croton acylated catapol derivative as well as preparation method and application thereof
  • Croton acylated catapol derivative as well as preparation method and application thereof
  • Croton acylated catapol derivative as well as preparation method and application thereof

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Example Embodiment

[0052] Example 1

[0053] A crotonylated catalpol derivative prepared by esterification of catalpol and crotonic anhydride. During esterification, all hydroxyl groups of catalpol and crotonic anhydride undergo an esterification reaction.

[0054] The method for preparing crotonylated catalpol derivatives includes the following steps:

[0055] 1) Dissolve 100mg (0.27mmol) of catalpol in 10mL of triethylamine, add 3.5mg of catalyst 4-dimethylaminopyridine, under nitrogen protection, add 759μL (4.86mmol) of crotonic anhydride, and react at 60°C for 36h, The liquid phase monitoring reaction is over, the esterification yield is 99.16% by mass spectrometry, and the triethylamine is evaporated to dryness by rotary evaporation to obtain the product;

[0056] 2) Dissolve the product of step 1) in 40 mL of dichloromethane, add 40 mL of alkaline agent-saturated sodium bicarbonate solution, stand for layering, discard the upper aqueous phase (add saturated sodium bicarbonate solution, stand for ...

Example Embodiment

[0058] Example 2

[0059] A crotonylated catalpol derivative prepared by esterification of catalpol and crotonic anhydride. During esterification, part of the hydroxyl groups of catalpol and crotonic anhydride undergo an esterification reaction.

[0060] The method for preparing crotonylated catalpol derivatives includes the following steps:

[0061] 1) Dissolve 0.27mmol catalpol in 6.7mL triethylamine, add 3.3mg of catalyst 4-dimethylaminopyridine, add 1.63mmo crotonic anhydride under nitrogen protection, react at 30℃ for 24h, and monitor the end of the reaction in liquid phase , The esterification yield was 98.53% by mass spectrometry, and the triethylamine was evaporated by rotary evaporation to obtain the product;

[0062] 2) Dissolve the product of step 1) in 30 mL of dichloromethane, add 20 mL of alkaline agent-saturated sodium bicarbonate solution, stand for layering, discard the upper aqueous phase (add saturated sodium bicarbonate solution, stand for layering, Discard the u...

Example Embodiment

[0064] Example 3

[0065] A crotonylated catalpol derivative prepared by esterification of catalpol and crotonic anhydride. During esterification, part of the hydroxyl groups of catalpol and crotonic anhydride undergo an esterification reaction.

[0066] The method for preparing crotonylated catalpol derivatives includes the following steps:

[0067] 1) Dissolve 100mg (0.27mmol) of catalpol in 5mL of triethylamine, add 3.1mg of catalyst 4-dimethylaminopyridine, under nitrogen protection, add 3.24mmol of crotonic anhydride, react at 90°C for 12h, and monitor the liquid phase After the reaction is over, the esterification yield is 97.21% by mass spectrometry, and the triethylamine is evaporated by rotary evaporation to obtain the product;

[0068] 2) Dissolve the product of step 1) in 40 mL of dichloromethane, add 40 mL of alkaline agent-saturated sodium bicarbonate solution, stand for layering, discard the upper aqueous phase (add saturated sodium bicarbonate solution, stand for layer...

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Abstract

The invention discloses a croton acylated catapol derivative which is prepared by esterifying catalpol and crotonic anhydride. The invention provides a corresponding preparation method and application, and the preparation method comprises the following steps: 1) dissolving catalpol into triethylamine, adding a catalyst 4-dimethylaminopyridine, adding crotonic anhydride under protection of nitrogengas, reacting for 12-36 hours at a temperature of 30-90 DEG C, and drying triethylamine by distilling to obtain a product, wherein a molar ratio of crotonic anhydride to catalpol is (6-18) to 1, anda molar ratio of 4-dimethylaminopyridine to catalpol is 1 to (9.5-10.5); and 2) dissolving the product in the step 1) into dichloromethane, adding an alkaline agent, standing and layering, discardingan upper-layer water phase, drying an organic phase to remove water, drying dichloromethane by distilling, purifying and separating, evaporating-drying, and filtering to obtain the catapol derivative.The catapol derivative has good anti-ageing activity, improves blood-brain barrier permeability of catapol, and has an esterification rate of 99.16%.

Description

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

Claims

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Application Information

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IPC IPC(8): C07H1/00C07H17/04A61P39/00
CPCA61P39/00C07H1/00C07H17/04
Inventor 董春红陈晓辉褚铭林王国庆张海燕程晓东张振强王强胡锴
Owner HENAN UNIV OF CHINESE MEDICINE
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