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Preparation and application of 8-phenylxanthine derivatives

A technology of phenylxanthine and its derivatives, which is applied in the field of preparation and anti-tumor activity, can solve the problems that the anti-tumor activity has not been reported in the literature, and achieve the effects of reasonable design of synthesis reaction, high yield and remarkable effect

Inactive Publication Date: 2015-11-25
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At the same time, xanthine derivatives also have a wide range of antiviral activities, but the antitumor activity of these compounds has not been reported in the literature

Method used

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  • Preparation and application of 8-phenylxanthine derivatives
  • Preparation and application of 8-phenylxanthine derivatives
  • Preparation and application of 8-phenylxanthine derivatives

Examples

Experimental program
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Effect test

Embodiment 1

[0032] Embodiment 1: the preparation of 8-[3-(benzamido) phenyl]-1,3,-dimethylxanthine

[0033] First prepare 3-benzamide benzoic acid. Dissolve m-aminobenzoic acid (3.00g) in dichloromethane (40ml), add triethylamine dropwise until the solution is clear, continue stirring for 30min, slowly add benzoyl chloride dropwise, until a large amount of white precipitates are formed, continue stirring for 2h, until After the reaction is complete, filter with suction, wash with water, dry, and recrystallize with acetic acid to obtain white crystals, filter with suction, and dry.

[0034] Get the 3-benzamide benzoic acid (2.2mmol) prepared above and 5,6-diamino-1,3-dimethyluracil (2.2mmol), EDC.HCl (2.21mol) and dioxane ( 30ml) and water (30ml) were mixed evenly, and after stirring for 30min, it turned yellow and turbid, and continued to stir for 8h until the reaction was complete; put it in the refrigerator to cool, filter, and wash with water to obtain a white solid; dissolve the whit...

Embodiment 2

[0035] Example 2: Preparation of 8-[3-(benzamido)phenyl]-1,3,7-trimethylxanthine

[0036] Take the 8-[3-(benzamido)phenyl]-1,3-dimethylxanthine (1.0mmol) prepared above and anhydrous K 2 CO 3 (1.0mmol) were mixed, DMF (20ml) was added, CH was added dropwise 3 I (1.0 mmol), refluxed at 60°C for 1 h, removed the insoluble matter by suction filtration, and obtained a clear light yellow liquid, added an appropriate amount of water, precipitated a white precipitate, washed with hot methanol, and recrystallized with DMSO to obtain the product with a yield of 40%. The parameters of the product are as follows: m.p.>300°C; ESI-MS: m / z=390[M+H] + ; 1 H-NMR (CDCl 3 )δ: 3.41(s, 3H), 3.60(s, 3H), 4.10(s, 3H), 7.46(d, 2H, J=8Hz), 7.49(t, 1H, J=8Hz), 7.55(d, 1H, J=12Hz), 8.7.70(d, 2H, J=12Hz), 7.87(d, 2H, J=12Hz), 8.03(s, 1H), 10.520(s, 1H).

Embodiment 3

[0037]Example 3: Preparation of 8-[4-(4-methyl-benzamido)phenyl]-1,3-dimethylxanthine

[0038] 4-(4-Methoxy)benzamide benzoic acid is first prepared. According to the method for preparing 3-benzamide benzoic acid among the embodiment 1, wherein just replace benzoyl chloride with 4-methoxybenzoyl chloride, replace 3-aminobenzoic acid with p-aminobenzoic acid.

[0039] Take the 4-(4-methoxy)-benzoylbenzoic acid (2.2mmol) prepared above and 5,6-diamino-1,3-dimethyluracil (2.2mmol), EDC.HCl (2.21 mol) and the mixed solution of dioxane (30ml) and water (30ml) were mixed evenly, and after stirring for 30min, it became yellow and turbid, and continued to stir for 8h until the reaction was complete; cool in the refrigerator, filter, and wash with water to obtain a white solid; Dissolve the white solid in a mixed solvent of 1NNaOH (10ml) and dioxane (10ml), heat to turn into a brown clear liquid, heat at 90°C-105°C for 8 hours, until complete reaction, cool to 0°C, add dilute hydrochl...

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Abstract

The invention belongs to the chemical synthetic technology of a medicine and discloses a synthetic method of 8-benzyl xanthine derivative which has anti-tumor activity and an application thereof. The compound provided by the invention has a structure of formula (I). The compound is used to treat cancer diseases. The anti-tumor activity in vitro experiment shows that the compound has a remarkable inhibiting and killing effect to various tumor cells.

Description

technical field [0001] The invention belongs to the field of chemical synthesis of medicines. Specifically, the invention relates to xanthine derivatives, the preparation of the 8-phenylxanthine derivatives and the application of anti-tumor activity. Background of the invention [0002] Xanthine alkaloids are widely found in plants in nature, including caffeine, theophylline, and theobromine. [0003] With the deepening of research, more and more xanthine derivatives have been isolated or synthesized and found to have many activities. [0004] Pharmacological studies have shown that the mechanism of action of xanthine derivatives is mainly to inhibit phosphodiesterase that can decompose and destroy cAMP, and increase the content of intracellular cAMP, thereby producing a wide range of physiological activities. (Ren Junguo, New Advances in Xanthine Drugs, Foreign Medicine—Synthetic Drugs, Biochemical Drugs, Preparations, 1989, 10(5): 272-276.) Specifically including stimulat...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D473/08C07D473/12A61K31/522A61P35/00
Inventor 叶发青胡素文宋博年四昀肖彤秦奎铕梁广李校堃陈江帆何金彩齐晓璐李玲娜胡国新
Owner WENZHOU MEDICAL UNIV
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