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Carbamate endocyclic xanthone derivative and preparation method and medicinal application thereof

A pharmaceutical and alkyl technology, which is applied in the field of carbamate-bridged xanthone derivatives and their preparation, can solve the problems affecting anti-tumor activity and achieve good anti-tumor activity and novel structure

Active Publication Date: 2015-12-09
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Poor water solubility seriously affects the antitumor activity of compound 1 in vivo (Journal of Medicinal Chemistry 56(2013) 276-292)

Method used

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  • Carbamate endocyclic xanthone derivative and preparation method and medicinal application thereof
  • Carbamate endocyclic xanthone derivative and preparation method and medicinal application thereof
  • Carbamate endocyclic xanthone derivative and preparation method and medicinal application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] 8-N,N-Dimethylcarbamoyloxy-3,3-dimethyl-1-(3-methylbut-2-en-1-yl)-3,3a,4,5-tetrahydro Synthesis of -1,5-methyl-1H,7H-furo[3,4-d]xanthene-7,13-dione (I-1)

[0043]

[0044] Compound 1a (80mg, 0.2mmol) was dissolved in acetone, and N,N-dimethylcarbamoyl chloride (34.24mg, 0.32mmol), potassium carbonate (43mg, 0.32mmol), DMAP (28mg, 0.24mmol) were added sequentially, N 2 protected and reacted overnight at room temperature.

[0045] The solvent was distilled off from the reaction solution under reduced pressure, and CH 2 Cl 2 dissolved, washed once with saturated ammonium chloride aqueous solution (20ml), washed with water (20ml), washed with saturated brine (20mL), anhydrous NaSO 4 Dry, filter with suction, and concentrate the filtrate to obtain a crude solid product, which is separated and purified by silica gel column chromatography (eluted with petroleum ether / ethyl acetate system) to obtain light yellow target product I-175 mg, with a yield of 76.53%. m.p.133.2...

Embodiment 2

[0047] 8-N,N-Diethylcarbamoyloxy-3,3-dimethyl-1-(3-methylbut-2-en-1-yl)-3,3a,4,5-tetrahydro Synthesis of -1,5-methyl-1H,7H-furo[3,4-d]xanthene-7,13-dione (I-2)

[0048]

[0049] Compound 1a (80mg, 0.2mmol) was dissolved in acetone, and N,N-diethylcarbamoyl chloride (43.24mg, 0.32mmol), triethylamine (0.044mL, 0.32mmol), DMAP (28mg, 0.24mmol) were added successively ), N 2 protected and reacted overnight at room temperature. The solvent was distilled off from the reaction solution under reduced pressure, and CH 2 Cl 2 dissolved, washed once with saturated ammonium chloride aqueous solution (20ml), washed with water (20ml), washed with saturated brine (20mL), anhydrous NaSO 4 Dry, filter with suction, and concentrate the filtrate to obtain a crude solid product, which is separated and purified by silica gel column chromatography (eluted with petroleum ether / ethyl acetate system) to obtain the light yellow target product I-279 mg, with a yield of 75.89%. m.p.144.6-146.4°C...

Embodiment 3

[0051] 8-N-methyl-N-ethylformyloxy-3,3-dimethyl-1-(3-methylbut-2-en-1-yl)-3,3a,4,5- Synthesis of Tetrahydro-1,5-methyl-1H,7H-furo[3,4-d]xanthene-7,13-dione (I-3)

[0052]

[0053]Compound 1a (80mg, 0.2mmol) was dissolved in dichloromethane, and N-methyl-Nethylcarbamoyl chloride (29.76mg, 0.32mmol), potassium carbonate (43mg, 0.32mmol), DMAP (28mg, 0.24mmol), N 2 protected and reacted overnight at room temperature. The solvent was distilled off from the reaction solution under reduced pressure, and CH 2 Cl 2 dissolved, washed once with saturated ammonium chloride aqueous solution (20ml), washed with water (20ml), washed with saturated brine (20mL), anhydrous NaSO 4 Dry, filter with suction, and concentrate the filtrate to obtain a crude solid, which is separated and purified by silica gel column chromatography (eluted with petroleum ether / ethyl acetate system) to obtain 368 mg of the white target product I-368 mg, with a yield of 73.11%. m.p.138-142°C; 1 HNMR (300MHz, ...

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Abstract

The invention relates to the field of medicinal chemistry, in particular to a carbamate endocyclic xanthone derivative (I) and a preparation method and medicinal application thereof. The derivative is a structural analogue of garcinia natural product gambogic acid, has an anti-tumor effect and can be used for preparing anti-tumor medicine, and the growth inhibition activity for kinds of tumor cells is at the micromole and sub-micromole level (the formula is as shown in specifications).

Description

technical field [0001] The present invention relates to the field of medicinal chemistry. It specifically relates to a class of carbamate bridged ring xanthone derivatives, a preparation method thereof and an application thereof in pharmacy. The derivatives are structural analogues of gambogic acid, a natural product of the genus Garcinia, have antitumor effects, and can be used for preparing antitumor drugs. Background technique [0002] Garcinia cambogia is a gelatinous resin secreted by splitting trunks of Garcinia genus plants in tropical and subtropical regions. It has been used as a medicine in Asia for hundreds of years. Among them, the antitumor activity of the natural product gambogic acid (gambogic acid / GA) is the most significant. Studies have shown that gambogic acid can selectively kill tumor cells, but has no obvious effect on normal hematopoietic system and white blood cells. Studies have shown that gambogic acid can increase the expression of the tumor sup...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/10A61P35/00
CPCC07D493/10
Inventor 张晓进尤启冬胡明阳李想孙昊鹏
Owner CHINA PHARM UNIV
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