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1-oxy-acetyl inula britannica lactone derivative, preparation method thereof and application of the same in preparing cancer-curing medicine

A technology of Inula grandiflora and Inula grandiflora, applied in drug combination, antineoplastic drugs, organic chemistry, etc., can solve the problems of weak pharmacological activity and inability to meet clinical needs, and achieve significant anticancer activity

Inactive Publication Date: 2008-05-28
HEBEI MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it is regrettable that the pharmacological activity of the above-mentioned single compound is weak and cannot meet the clinical needs.

Method used

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  • 1-oxy-acetyl inula britannica lactone derivative, preparation method thereof and application of the same in preparing cancer-curing medicine
  • 1-oxy-acetyl inula britannica lactone derivative, preparation method thereof and application of the same in preparing cancer-curing medicine
  • 1-oxy-acetyl inula britannica lactone derivative, preparation method thereof and application of the same in preparing cancer-curing medicine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0091] One of the methods for preparing compound (V)

[0092] With 1-O-ABL 113.2mg (0.4mmol), 2-(4-isobutylphenyl) propionic acid 85.7mg (0.4mmol) DMAP (4-dimethylaminopyridine) 58.6mg (0.4mmol) DCC99.3mg (0.45mmol) was dissolved in 3.5ml of dichloromethane and stirred at room temperature for 24h. After the reaction solution was diluted with 20ml of dichloromethane, it was washed with 5% HCl (20ml), saturated NaHCO3 solution (15ml×2), and then with saturated NaCl solution (15ml) until neutral, and dried overnight with anhydrous MgSO4. After filtration, dichloromethane was distilled off under reduced pressure to obtain a white solid. Separation by silica gel G column chromatography [petroleum ether-ethyl acetate (3:1)], the oily substance 64(S)-2-(4-isobutylphenyl)propionyl]-1-O-ABL (36mg ) yield 23% and 6-[(R)-2-(4-isobutylphenyl)propionyl]-1-O-ABL (78 mg) yield 45%.

[0093] The compound has the following physical properties:

[0094] colorless oil;

[0095] Spectral data:...

Embodiment 2

[0104] The second method of preparing compound (V)

[0105] (1) Preparation of 2-(4-isobutylphenyl) propionyl chloride

[0106] Take 500mg (2.4mmol) of 2-(4-isobutylphenyl)propionic acid, add 2ml of thionyl chloride, heat and reflux until no HCl gas overflows, after the reaction is complete, remove excess thionyl chloride by distillation under reduced pressure, add Dilute with 5ml of dichloromethane and set aside.

[0107] (2) Dissolve 100mg (0.37mmol) of 1-O-ABL and 50mg (0.4mmol) of DMAP in 5ml of dichloromethane, cool in an ice bath to 0°C, stir and add the above acid chloride dropwise, after 20min, remove the ice after 1h of reaction After the reaction is completed, the reaction solution is diluted with 20ml of dichloromethane, washed with 5% HCl (30ml), saturated NaHCO3 solution (30ml × 2), and then washed with saturated NaCl solution (30ml) to medium properties, dried over anhydrous MgSO4 overnight. After filtering, the dichloromethane was distilled off under reduced ...

Embodiment 3

[0110] Preparation of compound (VI)

[0111] Take 1-O-ABL and phenylacetic acid for condensation reaction. The specific reaction conditions are the same as in Example 1 to generate 6-(2-phenylacetoxy)-1-O-ABL. The yield was 41%.

[0112] The compound has the following physical properties:

[0113] Colorless oil.

[0114] Spectral data:

[0115] 1 HNMR (CDCl 3 , ppm): 0.96 (d, 3, 15-CH 3 ), 1.03(m, 1, H-3a), 1.27(m, 2, H-3b, H-2a), 1.41(m, 1, H-2a), 1.80(s, 3, 14-CH 3 ), 2.05 (s, 3, COCH 3 ), 2.50(dd, H, H-9a), 2.74(dd, 2, H-9b, H-4), 3.52(dd, 1, H-7), 3.93(m, 2, H-1), 4.94(t, 1, H-8), 5.3(s, 1, H-6), 5.45(d, 1, H-13a), 6.35(d, 1, H-13b), 3.6(d, 2, Ar-C H 2 ), 7.2 (dd, 2, Ar -CH 2 ), 7.34 (dd, 2, Ar -CH 2 ), 7.26 (dd, 1, pH -CH 2 ).

[0116] Elemental analysis: calculated to contain C, 70.40; H, 7.09; O, 22.51; measured to contain C, 70.43; H, 7.10; O, 22.47

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Abstract

The invention discloses a 1-oxygen-acetyl-hana-flowered-lactone derivative, relative preparation method and relative application in the drug preparation for treating cancer. The inventive preparation method comprises that 1-oxygen-acetyl-hana-flowered-lactone is directly condensed with relative acyl chloride to obtain product, or in the presence of catalytic condenser, 1-oxygen-acetyl-hana-flowered-lactone and relative acid are directly dewatered and acylated to obtain product. The inventive 1-oxygen-acetyl-hana-flowered-lactone derivative has significant cancer resistant activity, while the drug agent which active component is the inventive compound can be used for cancer treatment or cancer adjuvant treatment, in particular for leukemia, liver cancer and lung cancer.

Description

technical field [0001] The present invention relates to derivatives of compounds and their preparation methods and their application in the preparation of pharmaceutical preparations, in particular to 1-oxo-acetyl inulalide derivatives and their preparation methods and their use in the preparation and treatment of cancer application in medicine. Background technique [0002] In recent years, people have isolated and extracted three split eucalyptane-type sesquiterpenes (namely: 1-hydroxy-inula britannica L, 1-oxo-acetyl inula britannica L) from Inula britannica L. inulalide, 1,6-dioxo-diacetyl inulalide), and its pharmacological activity has been extensively studied. Studies have found that 1-oxo-acetyl inulalide has inhibitory nitric oxide synthase activity and anti-inflammatory activity (see references for details: Je KH, Han AR, Lee HT, et al. The inhibitory principle of lipopolysaccharide -induced nitric oxide production from Inula britannica var.chinensis.Arch Pharm R...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/83C07D407/12A61K31/365A61K31/443A61P35/00
Inventor 张嫡群温进坤吴一兵付焱王云志石晓伟祁金龙
Owner HEBEI MEDICAL UNIVERSITY
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