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Preparation method and application of parthenolide analog

A kind of technology of parthenolide and analogs, which is applied in the preparation of parthenolide analogs and the application field of preparing anticancer drugs

Active Publication Date: 2019-06-04
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, it is speculated that parthenolide selectively eliminates the mechanism of action of acute myeloid leukemia stem cells: the sulfhydryl group on Cys38 of p65 / NF-κB subunit and the outer ring of α-methylene-γ-butyrolactone of parthenolide 1,4-Michael addition to the double bond inhibits NF-κB activation

Method used

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  • Preparation method and application of parthenolide analog
  • Preparation method and application of parthenolide analog
  • Preparation method and application of parthenolide analog

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The synthesis of embodiment 1 compound 3a-3c

[0028]

[0029] Weigh Zn powder (2.0mmol) in a 100mL round bottom flask, add 5mL tetrahydrofuran, slowly add 2-bromoethyl methacrylate (2.0mmol), N 2 For replacement protection, the reaction solution was heated with a heat gun and ultrasonicated until the Zn powder was completely dissolved, then aldehyde (1.0 mmol) was slowly added dropwise, and the reaction was carried out at room temperature for 10-15 minutes (monitoring the reaction progress by TLC). After the reaction, THF was removed by rotary evaporation under reduced pressure, quenched by adding water, extracted three times with ethyl acetate, collected the organic phase, washed three times with saturated brine, dried with anhydrous sodium sulfate, and the concentrated column layer Analysis and purification [eluent: V (petroleum ether): V (ethyl acetate) = 10:1-5:1] to obtain target compounds 3a-3c.

[0030] Compound 3a [eluent: V (petroleum ether): V (ethyl acet...

Embodiment 2

[0035] The synthesis of embodiment 2 compound 4a-4c

[0036]

[0037] The lactone compound (1.0 mmol) was weighed and dissolved in dichloromethane, placed in an ice bath, the compound MCPBA (1.5 mmol) was weighed and added to the reaction solution, and the reaction was carried out for 30 min and moved to room temperature (reaction progress was monitored by TLC). After the reaction, wash the organic phase 3 times with 1M NaOH aqueous solution, collect the organic phase, and wash the organic phase with anhydrous NaSO 4 After drying, the concentrated product was rotary evaporated under reduced pressure and purified by column chromatography [eluent: V (petroleum ether): V (ethyl acetate) = 10:1-5:1] to obtain compounds 4a-4c.

[0038]

[0039] Compound 4a [eluent: V (petroleum ether): V (ethyl acetate) = 10:1-4:1]: white solid, melting point 59.8°C, yield 80%; 1 H NMR (300MHz, CDCl 3 )δ7.31-7.16(m,5H),6.22-6.20(t,J=3.0Hz,1H),5.65-5.63(t,J=3.0Hz,1H),4.60-4.54(m,1H),3.74 -3...

Embodiment 3

[0044] The synthesis of embodiment 3 compound 5a-5h

[0045]

[0046] NaOH (1.0mmol) and H 2 o 2 (1.0mmol) was slowly added to a round-bottomed flask, 10mL MeOH was added, and then substrate aldehyde or ketone (1.0mmol) was added, and reacted at room temperature for 10min (reaction progress was monitored by TLC). Purified by column chromatography [V (petroleum ether): V (ethyl acetate) = 10:1 ~ 5:1] to obtain compounds 5a-5f.

[0047]

[0048] Compound 5a [eluent: V (petroleum ether): V (ethyl acetate) = 8:1-5:1]: white solid, yield 80%; 1 HNMR (300MHz, CDCl 3 )δ7.31-7.39 (m, 5H), 3.94-3.93 (d, J = 3.0Hz, 1H), 3.43-3.42 (d, J = 3.0Hz, 1H), 2.13 (s, 3H); 13 C NMR (75MHz, CDCl 3 )δ203.2, 134.0, 128.0, 127.7, 124.7, 62.4, 56.7, 23.8

[0049]

[0050] Compound 5b [eluent: V (petroleum ether): V (ethyl acetate) = 10:1-5:1]: white solid, yield 85%; 1 HNMR (300MHz, CDCl 3 )δ7.93-7.90(m,2H),7.56-7.50(m,1H),7.42-7.37(m,2H),7.42-7.26(m,5H),4.22-4.21(d,J=3.0Hz, 1H), 3.9...

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Abstract

The invention relates to a preparation method and applications of parthenolide analogues, and belongs to the field of organic synthesis. On the basis of reserving the main active group alpha-methylene-gamma-lactone and epoxide structure of parthenolide, series of compounds are designed by changing its framework, and its in-vitro antitumor activity is tested. Series of parthenolide analogues having biological activity are synthesized by a simple method, wherein two compounds are nontoxic to normal cells.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a preparation method of parthenolide analogues and their application as preparation of anticancer drugs Background technique [0002] Wild chamomile originated in the Balkan Peninsula. The earliest Europeans and Greeks planted and used wild chamomile for ornamental and medicinal purposes. Because of its anti-inflammatory activity, wild chamomile is often used to treat arthritis, in addition, it is also a good anticoagulant, digestive, anthelmintic, and can treat depression, vertigo, kidney disease, etc. Stones and other diseases. Until 1978, feverfew's stress-reducing effects were reported in the British Journal of Health, and it was widely cultivated as a herbal medicine for this reason. In 1997 the main active ingredient of this best-selling phytopharmaceutical was identified as parthenolide and purified. Parthenolide is mainly found in the branches, flowers and leaves of pl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D407/04C07D407/14C07D493/10A61K31/365A61P35/00
CPCC07D407/04C07D407/14C07D493/10
Inventor 任杰刘瑜胡昆钟健许园元赵月欣
Owner CHANGZHOU UNIV
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