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Coumestrol open-ring analogue and medical application thereof

A pharmacy and drug technology, which is applied to the ring-opening analog of coumestrol to prepare the field of drugs as angiogenesis inhibitor and vascular blocker, and can solve the problems of no very satisfactory treatment method, low toxicity and high efficiency, etc.

Active Publication Date: 2015-06-17
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Cancer has become a major disease that seriously endangers human health and life, and there is still no satisfactory treatment method so far, so it is imminent to develop anti-tumor drugs with low toxicity and high efficiency

Method used

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  • Coumestrol open-ring analogue and medical application thereof
  • Coumestrol open-ring analogue and medical application thereof
  • Coumestrol open-ring analogue and medical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Synthesis of 1-(2,4-dihydroxyphenyl)-2-(4-methoxyphenyl)ethanone (11)

[0033] Dissolve 3.60 g (32.5 mmol) of resorcinol in 50 ml of newly steamed boron trifluoride ether solution, and then add 5.00 g (30.0 mmol) of p-methoxyphenylacetic acid. The mixture was reacted at 100°C, the end point was determined by TLC, washed and extracted three times with saturated sodium bicarbonate solution, and the organic phase was dried overnight by adding anhydrous sodium sulfate. Concentrate under reduced pressure to remove the solvent, and recrystallize the crude product from absolute ethanol to obtain 5.95 g of off-white powder with a yield of 77%, mp150-152 °C, EI-MS m / z: 259 [M+H] + .

Embodiment 2

[0035] Synthesis of 4,7-dihydroxy-3-(4-methoxyphenyl)-coumarin (12)

[0036] Add 4.4 g of compound 11 (17.05 mmol) and 8.2 g of NaH (341 mmol) into 120 ml of diethyl carbonate, react at 80° C. under nitrogen protection, and determine the end point by TLC. Add 100ml of water into the reaction liquid, separate the liquids, discard the organic phase, extract the water phase with ethyl acetate three times, adjust the pH of the water phase to 3-4 with 1mol / L hydrochloric acid, a large amount of white solid precipitates out, and suction filter to obtain the crude product , after purification by column chromatography, 3.8g white powder was obtained, the yield was 80%, ESI-MS m / z: 283[M-H] - .

Embodiment 3

[0038] Synthesis of N-Chloroethylpyrrolidine Hydrochloride

[0039] 4.6ml of pyrrolidine (57.5mmol) and 4.6ml of 2-chloroethanol (69.0mmol) were added to 40ml of toluene, heated to reflux for 2 hours, the reaction solution was cooled to room temperature, and 8.4ml of thionyl chloride (114mmol ), after 20 minutes of dripping, the ice bath was removed, stirred at room temperature for 6 hours, the toluene and thionyl chloride were evaporated under reduced pressure, and the residual solid was recrystallized with ethanol to obtain 8.3 g of chloroethylpyrrolidine hydrochloride.

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PUM

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Abstract

The invention relates to the field of pharmaceutical chemistry, in particular to a coumestrol open-ring analogue with structures as shown in general formulae I and II and a medical application thereof, especially an application to the preparation of drugs as angiogenesis inhibition and vascular disruption agents.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a ring-opening analogue of coumestrol and its medical application, especially the application for preparing drugs as an angiogenesis inhibitor and a blood vessel blocking agent. Background technique [0002] Tumors are diseases characterized by the uncontrolled proliferation and spread of abnormal cells. The American Cancer Society's 2014 "Global Cancer Facts and Figures" report shows that in 2012, there were 14 million new cancer cases and 8.2 million deaths worldwide, of which, 3.07 million new cancer patients and about 2.2 million deaths were caused in China , accounting for 21.9% and 26.8% of the global total, respectively. The report predicts that global cancer cases will show a rapid growth trend, from 14 million in 2012 to 19 million in 2025 and 24 million in 2035. Cancer has become a major disease that seriously endangers human health and life, and there is still no s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/56C07D307/84A61K31/352A61K31/4025A61K31/4525A61K31/453A61K31/5377A61K31/343A61P35/00
Inventor 向华唐郑普骆国顺牛绍雄王文宾郭静沫陈明琪尤启冬
Owner CHINA PHARM UNIV
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