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Cracked-ring lupane derivatives and pharmaceutical application thereof

A technology of lupine and its derivatives, which is applied in the direction of androstane derivatives, drug combinations, antipyretics, etc., and can solve the problems of high incidence of thrombotic diseases and high clinical costs

Inactive Publication Date: 2017-12-22
JILIN AGRICULTURAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] High morbidity and clinical costs of thrombotic disease

Method used

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  • Cracked-ring lupane derivatives and pharmaceutical application thereof
  • Cracked-ring lupane derivatives and pharmaceutical application thereof
  • Cracked-ring lupane derivatives and pharmaceutical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: Synthesis of split ring lupin derivatives

[0027] 1.1 Instruments and reagents

[0028] 1 HNMR nuclear magnetic resonance spectrum adopts Bruker AVII 500 superconducting nuclear magnetic resonance instrument; HRMS mass spectrometry adopts UPLC-XevoG 2 -S QTOF-MS / MS. Derivative 1 is self-made in the laboratory (purity ≥ 98%), and other reagents are domestic analytical reagents.

[0029] 1.2 Synthesis of derivatives

[0030] 1.2.1 Synthesis of Derivative 2

[0031] Dissolve derivative 1 (484.0mg, 1.0mmol) in 50mL of dichloromethane, add vanadyl acetylacetonate (26.0mg, 0.1mmol), stir well and add 70% tert-butyl hydroperoxide aqueous solution (413μL, 3mmol) , react at room temperature for 3 hours, add 30mL aqueous sodium bicarbonate solution, stir for 15 minutes, extract 3 times with ethyl acetate 30mL, combine the organic layers, wash with saturated brine, dry over anhydrous sodium sulfate, and recover the solvent under reduced pressure to obtain derivati...

Embodiment 2

[0063] Example 2: P2Y12 receptor antagonist effect test of split-lupene derivatives

[0064] 2.1 Method: Blood was collected from healthy volunteers using a 20 mL syringe containing 2 mL of buffered sodium citrate. Blood was transferred to polypropylene tubes and centrifuged (100 g) for 5 min at room temperature. The platelet-rich plasma (PRP) floating on the surface was then collected, diluted, and platelet counts were performed before it was used for aggregation measurements.

[0065] Measurements of platelet aggregation (Aggregometer) were performed in glass tubes at 37°C. 4 μL of the test compound (DMSO solution 100-fold higher than the desired final concentration) was mixed with 392 μL of freshly prepared PRP and incubated for 1 min with stirring. Then add 4 μL of 250 μM ADP solution to the mixture. Stirring was continued and aggregation measurements were monitored for 6-8 min by recording the change in optical density according to the method of G.V.R. Born (Born. Natu...

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Abstract

The invention relates to cracked-ring lupane derivatives, a P2Y12 receptor antagonist function of pharmaceutical composition containing the cracked-ring lupane derivatives and an application of the cracked-ring lupane derivatives to preparation of drugs for preventing, treating and relieving thrombotic diseases. Conventional structural constraints of natural products are changed with a semisynthetic method, a series of cracked-ring lupane derivatives are designed and synthesized, the P2Y12 receptor antagonist function of the cracked-ring lupane derivatives is verified in vitro, and the compounds can be applied to research of the drugs for preventing, treating and relieving the thrombotic diseases through further experiments.

Description

technical field [0001] The invention belongs to the field of medicines, and in particular relates to a class of split ring lupin derivatives, pharmaceutical compositions containing them and their use in the preparation of preventing, treating or alleviating thrombotic diseases. More specifically, the present invention describes split-lupin derivatives that can be used as P2Y12 receptor antagonists and their related pharmaceutical applications. Background technique [0002] Thrombotic disease is a disease caused by two pathological processes of thrombosis and thromboembolism. Thrombotic disease is a serious threat to human life and health, and its incidence rate ranks first among various diseases, and it has gradually increased in recent years. It is one of the focuses and hotspots of contemporary medical research. Thrombosis refers to the pathological process in which the formed components of blood form emboli in blood vessels (mostly small blood vessels) under certain cond...

Claims

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Application Information

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IPC IPC(8): C07J71/00C07J1/00A61K31/585A61K31/565A61P7/02A61P29/00A61P7/10A61P9/10A61P9/04A61P9/06A61P13/12A61P1/00
CPCC07J71/0005C07J1/0007
Inventor 赵岩郭雪边兴博陈晨王伟东付天华尹永霞
Owner JILIN AGRICULTURAL UNIV
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