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Scutellarin aglycone nitrogen mustard derivative and preparation method and application thereof

A technology of scutellarin aglycone nitrogen mustards and derivatives, which is applied in the field of medicinal chemistry, can solve the problems of high toxicity and side effects, and achieve obvious anti-tumor activity

Active Publication Date: 2018-11-23
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, nitrogen mustards have no selectivity for normal and tumor cells, and have relatively large toxic and side effects

Method used

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  • Scutellarin aglycone nitrogen mustard derivative and preparation method and application thereof
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  • Scutellarin aglycone nitrogen mustard derivative and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0030]

[0031] Add scutellarin 1 (10g, 21.6mmol) to 120mL absolute ethanol, 120mL concentrated hydrochloric acid and 10mL H 2 O mixture. in N 2 Under the condition of protection, reflux for 36h. After cooling at room temperature, the reaction solution was poured into an equal volume of water, suction filtered, washed with water until neutral, dried, and the crude product was separated by silica gel column chromatography (petroleum ether: ethyl acetate 1:1) to obtain scutellarin as a yellow solid Yuan 5 1.05g, yield 17%. 1 H NMR (DMSO-d 6 ,400MHz)δ(ppm):12.80(s,1H,5-OH),10.47(s,1H,7-OH),10.32(s,1H,4′-OH),8.75(s,1H,6- OH), 7.91(d, 2H, J=8.9Hz, H-2′, 6′), 6.92(d, 2H, J=8.9Hz, H-3′, 5′), 6.75(s, 1H, H -8), 6.57(s, 1H, H-3).

Embodiment 2

[0033]

[0034] Dissolve scutellarin aglycone 5 (1 g, 3.5 mmol) in 50 mL of diphenyl ether, and add dichlorodiphenylmethane (1009 μL, 5.25 mmol). in N 2 Protection, under the condition of 175°C, react for 1.5h. After cooling at room temperature, the reaction solution was poured into 500 mL of petroleum ether, suction filtered, and dried. The crude product was separated by silica gel column chromatography (petroleum ether: ethyl acetate 2:1) to obtain 937 mg of a yellow solid with a yield of 59%. 1 H NMR (DMSO-d 6 ,400MHz)δ(ppm):13.17(s,1H,5-OH),10.41(s,1H,4′-OH),7.93(d,2H,J=8.7Hz,H-2′,6′) ,7.57-7.46(m,10H,Ar-H),7.06(s,1H,H-8),6.93(d,2H,J=8.7Hz,H-3′,5′),6.87(s,1H , H-3).

Embodiment 3

[0036]

[0037] Intermediate 6 (450mg, 1mmol) was dissolved in 30mL of acetone, and K 2 CO 3 (417mg, 3mmol) and 1,3-dibromopropane (420μL, 3mmol) were refluxed for 8h. After cooling at room temperature, it was filtered with suction, and the filtrate was concentrated and separated through a silica gel column (petroleum ether: ethyl acetate 6:1) to obtain 473 mg of light yellow powder 7a with a yield of 83%. 7a (285mg, 0.5mmol), dissolved in 5mL of DMF, added K 2 CO 3 (139mg, 1mmol) and benzoen mustard 4 (152mg, 0.5mmol), react at room temperature for 24h. The reaction solution was poured into 30 mL of H 2 O, extracted with ethyl acetate (3×20mL), washed with saturated saline solution, dried over anhydrous sodium sulfate, filtered, concentrated the filtrate, and separated by silica gel column chromatography (petroleum ether: ethyl acetate 4:1) to obtain light yellow powder 8a 323 mg, 86% yield. 8a was added to 10 mL of aqueous acetic acid, at 170 ℃ After reflux reactio...

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Abstract

The invention belongs to the field of natural medicine and medicinal chemistry and relates to a scutellarin aglycone nitrogen mustard derivative and a preparation method and application thereof, in particular to a scutellarin aglycone nitrogen mustard derivative of which 4'-OH is combined with benzoic acid nitrogen mustard and a preparation method and antitumor activity thereof. The structure of the scutellarin aglycone nitrogen mustard derivative and pharmaceutically acceptable salt thereof is as shown in the general formula I, wherein R and n are as described in claims and the specification.The formula I is shown in the description.

Description

technical field [0001] The present invention relates to the field of medicinal chemistry, and relates to a class of scutellarin aglycone nitrogen mustard derivatives and a preparation method and application thereof, in particular to a scutellarin aglycone nitrogen mustard derivative in which benzoic mustard is spliced ​​at 4′-OH Its preparation method and antitumor activity. Background technique [0002] Tumor is one of the major diseases that threaten human health. However, while clinical antitumor drugs show good activity, they also have more and more side effects, which seriously affect the therapeutic effect of tumor diseases. Therefore, it is particularly important to find and develop antitumor drugs with high efficiency and low toxicity. Natural products are the main source of drug discovery. Among the marketed anti-tumor drugs, many successful drugs are directly or indirectly derived from natural products. Therefore, it is very important to find and obtain anti-tumo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30C07D493/04A61P35/00A61P35/02A61K31/352
CPCA61P35/00A61P35/02C07D311/30C07D493/04Y02P20/55
Inventor 李达翃华会明韩通程克光李占林续繁星胡旭高祥
Owner SHENYANG PHARMA UNIVERSITY
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