Bergenin derivatives as well as preparation method and application thereof

A technology of petrolatum and derivatives, which is applied in the field of drug synthesis, can solve problems such as unreported research on petrolatum anti-tumor activity, and achieves the effects of good operability, good reaction yield and simple synthesis method.

Active Publication Date: 2014-07-16
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] There is no report on the research on the structural modification of petracenin and its derivatives' anti-tumor activity

Method used

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  • Bergenin derivatives as well as preparation method and application thereof
  • Bergenin derivatives as well as preparation method and application thereof
  • Bergenin derivatives as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 18

[0023] Example 18-O-isobutyl-bergenin and 8,10-di-O-isobutyl-bergenin

[0024] Weigh petracenin (100mg, 0.30mmol), sodium bicarbonate (76mg, 0.90mmol) and catalytic amount of KI, dissolve in 5ml anhydrous DMF, add bromoisobutane (73μL, 0.67mmol) dropwise at room temperature , after the dropwise addition was completed, it was gradually heated to 80°C under the protection of nitrogen, and reacted for 12 hours; after the reaction was completed, it was cooled to room temperature, added 15ml of water and 15ml of ethyl acetate for extraction, the aqueous phase was extracted three times with ethyl acetate, and the ethyl acetate phase was combined. Wash three times with water, and wash the ethyl acetate phase with anhydrous Na 2 SO 4 After drying, the residue obtained after evaporating the organic solvent under reduced pressure was subjected to silica gel column chromatography, and the eluent was petroleum ether: ethyl acetate = 1:1. 42.8 mg of compound (2) and 65.5 mg of compound (...

Embodiment 28

[0029] Example 28-O-(2-Butyl)-Bergenin and 8,10-Di-O-(2-Butyl)-Bergenin

[0030] Weigh petracenin (100mg, 0.30mmol), sodium bicarbonate (76mg, 0.90mmol) and catalytic amount of KI, dissolve in 5ml DMF, add bromo-sec-butane (73μL, 0.67mmol) dropwise at room temperature, drop After the addition, gradually heat to 80°C under nitrogen protection, and react for 12 hours; after the reaction, cool to room temperature, add 15ml of water and 15ml of ethyl acetate for extraction, extract the water phase with ethyl acetate three times, combine the ethyl acetate phase, and wash with water Three times, the ethyl acetate phase was washed with anhydrous Na 2 SO 4 After drying, the residue obtained after evaporating the organic solvent under reduced pressure was subjected to silica gel column chromatography, and the eluent was petroleum ether: ethyl acetate = 1:1. 33.3 mg of compound (4) and 42.3 mg of compound (5) were obtained, and the yields were 28% and 31%, respectively.

[0031] 8-O-...

Embodiment 38

[0035] Example 38-O-Isopentyl-Bergenin and 8,10-Di-O-Isopentyl-Bergenin

[0036] Weigh petracenin (100mg, 0.30mmol), sodium bicarbonate (76mg, 0.90mmol) and catalytic amount of KI, dissolve in 5ml DMF, add bromoisopentane (84μL, 0.70mmol) dropwise at room temperature, drop After the addition, gradually heat to 80°C under nitrogen protection, and react for 12 hours; after the reaction, cool to room temperature, add 15ml of water and 15ml of ethyl acetate for extraction, extract the water phase with ethyl acetate three times, combine the ethyl acetate phase, and wash with water Three times, the ethyl acetate phase was washed with anhydrous Na 2 SO 4 After drying, the residue obtained after evaporating the organic solvent under reduced pressure was subjected to silica gel column chromatography, and the eluent was petroleum ether: ethyl acetate = 1:1. 40.7 mg of compound (6) and 53.7 mg of compound (7) were obtained, and the yields were 33% and 37%, respectively.

[0037] 8-O-I...

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Abstract

The invention discloses bergenin derivatives as well as a preparation method andapplication thereof. The structure of the compounds is as shown in a formula II, wherein R1 is selected from C3-C10 alkyl groups or naphthenic bases, and R1 is selected from H, the C3-C10 alkyl groups or the naphthenic bases. According to the preparation method of the bergenin derivatives, bergenin and bromoalkane are used as raw materials and react under the effect of a catalyst so as to generate the compounds as shown in the formula II. The bergenin derivatives disclosed by the invention are applied in the preparation of medicines for treating prostate cancers. A series of bergenin derivatives are synthesized by using the bergenin and the bromoalkane as raw materials; based on natural products easy to obtain, a synthetic method is simple and has relatively good operability and reaction yield. The bergenin derivatives have remarkable effects on prostate cancer treatment and provide reference for the application of the bergenin compounds in the prostate cancer treatment. The formula II is as shown in the specification.

Description

technical field [0001] The invention belongs to the field of drug synthesis, and relates to petracenin derivatives and a preparation method thereof, as well as the application of the compounds in the preparation of antitumor drugs. Background technique [0002] [0003] Petgenin (Ⅰ) is the main active ingredient of saxifrage plants such as saxifrage, rock cabbage, thick-leaved rock cabbage, and low ground tea. Tablets are available for clinical use. In recent years, the saxifrage extract containing petogenin has anti-prostatic hyperplasia and anti-tumor activities. Extract different effective parts from saxifrage, and use flow cytometry to observe the inhibitory effect on fibroblasts cultured in vitro and the effect on cell apoptosis. The study found that saxifrage extract can inhibit fibroblasts in vitro proliferation and induce apoptosis of fibroblasts. Extract different effective parts from saxifrage, and use flow cytometry to observe the effect on the proliferation...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/04A61P35/00A61P13/08
CPCC07D493/04
Inventor 冯锋闫德彪柳文媛张冬萍郭青龙
Owner CHINA PHARM UNIV
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