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Iron feces mi-6-one derivatives and their preparation methods and uses

A technology of derivatives and iron feces, applied in the field of iron feces mi-6-one derivatives and its preparation, can solve problems such as low content and failure to carry out systematic research

Active Publication Date: 2019-03-29
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the content of this alkaloid in plants is not high, and systematic research has not been carried out

Method used

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  • Iron feces mi-6-one derivatives and their preparation methods and uses
  • Iron feces mi-6-one derivatives and their preparation methods and uses
  • Iron feces mi-6-one derivatives and their preparation methods and uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Example 1 Preparation of 2-carboxyironium-6-one

[0056] a, L-tryptophan methyl ester

[0057]

[0058] Add SOCl dropwise to 150 mL methanol solution in ice bath 2 (8mL, 107mmol), after the dropwise addition was completed, the ice bath was removed, and after stirring at room temperature for 1h, L-tryptophan (10g, 50mmol) was added, stirred at room temperature overnight, TLC detected that the reaction was complete, and the solvent was evaporated under reduced pressure to obtain a white solid , was dissolved in a small amount of methanol, the product was precipitated by adding excess glacial ether, and suction filtered to obtain a white product with a yield of 100%.

[0059] ESI-MS m / z: 219.1[M+H] + , relative molecular mass 218.

[0060] b. 1-dimethoxymethyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carbaline

[0061]

[0062] L-tryptophan methyl ester (5g, 23mmol) was dissolved in water, with 1mol / L H 2 SO 4 Adjust the pH between 2 and 3, add 60% glyoxal dimeth...

Embodiment 2

[0081] Example 2 Preparation of 2-ethoxycarbonylironium-6-one (CAN-1)

[0082]

[0083] 2-carboxyironium-6-ketone (25mg, 95mmol), 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDCI) (20mg, 105mmol) and catalytic An appropriate amount of 4-dimethylaminopyridine (DMAP) was dissolved in 25 mL of DMF (the function of EDCI and DMAP is to catalyze the formation of active intermediates of carboxyl groups, which is convenient to react with alcohols to form corresponding esters), and after stirring at room temperature for 1 h, add ethanol (6.1 μL , 105mmol), stirred overnight at room temperature, diluted with dichloromethane, extracted with water to remove water-soluble impurities, the organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure to obtain the mixture, purified by silica gel column chromatography, and the eluent was CH 2 Cl 2 : MeOH=50:1 V / V, 18.0 mg of a yellow solid was obtained, and the yield was 60.0%. It has been ide...

Embodiment 3

[0086] Example 3 Preparation of 2-isopropoxycarbonylironium-6-one (CAN-2)

[0087]

[0088] Dissolve 2-carboxyironium-6-one (25 mg, 95 mmol), EDCI (20 mg, 105 mmol) and a catalytic amount of DMAP in 25 mL of DMF, stir at room temperature for 1 h, then add isopropanol (8.0 μL, 105 mmol), Stir at room temperature overnight, dilute with dichloromethane, extract with water to remove water-soluble impurities, dry the organic layer with anhydrous sodium sulfate, concentrate under reduced pressure to obtain the mixture, and purify by silica gel column chromatography (CH 2 Cl 2 -MeOH 50:1), to obtain 20.3 mg of yellow solid, yield 70.0%. It was identified as 2-isopropoxycarbonylironium-6-one.

[0089] ESI-MS m / z: 329.1[M+Na] + , The relative molecular mass is 306.

[0090] 1 H NMR (500MHz, CDCl 3 )δ: 8.86(s, 1H), 8.72(d, J=8.2Hz, 1H), 8.22(s, 1H), 8.22(d, J=9.8Hz, 1H), 7.79(t, J=7.8Hz, 1H), 7.61(t, J=7.6Hz, 1H), 7.07(d, J=9.8Hz, 1H), 5.49(m, J=6.5Hz, 1H), 1.56(d, J=6.5Hz, 6H...

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PUM

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Abstract

The invention discloses a canthin-6-ketone derivative or salt and hydrate, capable of being accepted pharmaceutically, of the canthin-6-ketone derivative. The canthin-6-ketone derivative is shown in the structural formula I, wherein R1 is selected form -OR2, -NHR3, -NR4R5 and heterocyclic ring groups containing one or more N, R2 is selected from alkyl, substitutive alkyl, benzene ring substituted alkyl, naphthene, phenyl and substitutive phenyl except for methyl, and R3, R4 and R5 are independently selected from alkyl, benzene ring substituted alkyl, phenyl and substitutive phenyl respectively. The invention further discloses application of the canthin-6-ketone derivative or salt and hydrate, capable of being accepted pharmaceutically, of the canthin-6-ketone derivative to preparation of anti-tumor medicine. 2-carboxyl canthin-6-ketone raw materials are synthesized through six steps of reactions, then 2-carboxyl canthin-6-ketone is subjected to structural modification to prepare the canthin-6-ketone derivative, and the canthin-6-ketone derivative has remarkable inhibitory activity on A549 and HepG2. The formula is shown in the description.

Description

technical field [0001] The present invention relates to a kind of iron feces mi-6-one derivatives and its preparation method and application, in particular to a kind of iron feces mi-6-one 2-carboxyl derivatives and its preparation method, and the preparation of such compounds in the preparation of anti- Use in tumor medicine. Background technique [0002] Tumor is a new organism formed by the body under the action of various tumorigenic factors, and the cells of local tissues lose their normal regulation of their growth at the gene level, resulting in abnormal proliferation and differentiation. Once a new organism is formed, it does not stop growing due to the elimination of the cause. Its growth is not regulated by normal body physiology, but destroys normal tissues and organs. This is especially obvious in malignant tumors. Compared with benign tumors, malignant tumors grow faster and show invasive growth, are prone to bleeding, necrosis, ulcers, etc., and often have dis...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/16A61P35/00
CPCC07D471/16
Inventor 冯锋曲玮叶峰柳文媛张冬萍唐婧赵依凡
Owner CHINA PHARM UNIV