A kind of crotonylated catalpol derivative and its preparation method and application

A technology of crotonylation and derivatives, applied in the field of crotonylated catalpol derivatives and the preparation thereof, can solve the problems such as catalpol anhydride esterification derivatives that have not yet been found, achieve good anti-aging activity, reduce difficulty, low polar effect

Active Publication Date: 2020-09-18
HENAN UNIV OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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 Chemistry Letters, 2007, 17: 1332-133) have synthesized catalpol derivatives such as full acetyl group protection, No other anhydride esterification derivatives of catalpol have been found

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  • A kind of crotonylated catalpol derivative and its preparation method and application
  • A kind of crotonylated catalpol derivative and its preparation method and application
  • A kind of crotonylated catalpol derivative and its preparation method and application

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Embodiment 1

[0053] A crotonylated catalpol derivative obtained by esterifying catalpol with crotonic anhydride. During esterification, all hydroxyl groups of catalpol react with crotonic anhydride.

[0054] A method for preparing crotonylated catalpol derivatives, comprising the steps of:

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

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

Embodiment 2

[0059] A crotonylated catalpol derivative obtained by esterifying catalpol with crotonic anhydride. During esterification, some hydroxyl groups of catalpol react with crotonic anhydride.

[0060] A method for preparing crotonylated catalpol derivatives, comprising the steps of:

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

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

Embodiment 3

[0065] A crotonylated catalpol derivative obtained by esterifying catalpol with crotonic anhydride. During esterification, some hydroxyl groups of catalpol react with crotonic anhydride.

[0066] A method for preparing crotonylated catalpol derivatives, comprising the steps of:

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

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

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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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Patent Type & Authority Patents(China)
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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