Bergenin derivative as well as preparation method and application thereof

A technology of petracenin and derivatives, which is applied in the field of preparation and derivatives of petracenin, which can solve the problems of large drug resistance of toxic and side effects, and drugs can only alleviate the disease, etc.

Active Publication Date: 2015-06-24
XINXIANG MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Since the 1990s, more than 200 anticancer drugs have been under research and development worldwide, and dozens of chemotherapy or adjuvant drugs have been used in clinical treatment, but most drugs can only alleviate the disease
Moreover, most of the existing antineoplastic drugs are chemically synthesized drugs, which have problems such as large toxic and side effects, and easy drug resistance.

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Embodiment 1: the preparation of compound 1

[0049] (1) Take 1mmol petracenin and 3mmol KI, 2mmolK 2 CO 3 In the reaction solvent 3mL NMP, stir at room temperature until the sample is completely dissolved, then add 3mmol 3-bromopropyne, react at 60°C for 4h, and detect by TLC, the reaction is complete.

[0050] (2) After directly adding 15 mL of ethyl acetate and 15 mL of distilled water to the reaction system obtained in (1) for extraction, the organic layer was washed with 10 mL of saturated brine. Anhydrous NaSO for organic phase 4 Dry the powder for 15-30 minutes.

[0051] (3) The product obtained in step (2) is filtered, concentrated, separated and purified by silica gel column chromatography, and eluted with petroleum ether / ethyl acetate 1 / 1 (V / V), and the eluted part is concentrated to obtain a single white powder target product. The yield was 66.7%.

[0052] through 1 H NMR detection, the structural characterization of compound 1 is as follows:

[0053]...

Embodiment 2

[0055] Embodiment 2: the preparation of compound 2

[0056] 1. Preparation of azide compounds

[0057] Take 1 mmol of benzyl bromide and 2 mmol of sodium azide in a 5 mL dry round bottom flask, add 2 mL of DMF, and react at 30° C. for 10 h, and TLC detects that the reaction is complete. Add 10 mL of ether and 10 mL of distilled water to the reaction solution for extraction, wash the organic phase with 6 mL of saturated brine, and wash the organic layer with anhydrous NaSO 4 Dry for 15 to 30 minutes, filter, and concentrate to obtain benzyl-substituted azide compounds.

[0058] 2. Preparation of Compound 2 by Click Chemistry Principle

[0059] Take 0.1mmol compound 1 (40.2mg) and 0.25mmol benzyl-substituted azide in a 25mL dry round bottom flask, add 5mg of CuSO 4 ·5H 2 O, 5 mg sodium ascorbic acid in 3 mL THF-H 2 O(V / V=1 / 1) or 3mL t-BuOH-H 2 The 1,3-dipolar cycloaddition reaction was carried out in O (V / V=1 / 1) solvent at room temperature to generate compound 2 with a yie...

Embodiment 3

[0063] Embodiment 3: the preparation of compound 3

[0064] The difference between the preparation method of compound 3 and the preparation method of compound 2 is that 4-methylbenzyl azide is prepared by reacting 4-methylbenzyl chloride with sodium azide. The yield of compound 3 was 88.8% when using click chemistry principle.

[0065] through 1 H NMR detection, the structural characterization of compound 3 is as follows:

[0066] 1 H NMR (400MHz, CD 3 OD)δ8.02(s,1H),7.94(s,1H),7.51(s,1H),7.15(dd,J=14.2,10.1Hz,8H),5.51(s,2H),5.47(s, 2H), 5.15(d, J=11.5Hz, 1H), 5.05(d, J=11.5Hz, 1H), 4.46(d, J=10.3Hz, 1H), 3.88-3.77(m, 2H), 3.76( s,3H),3.68(dd,J=11.4,6.6Hz,1H),3.39(dd,J=18.1,9.8Hz,1H),3.29(s,2H),2.28(s,6H).

[0067] The analysis of the above nuclear magnetic detection data shows that the target product 3 is generated.

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Abstract

The invention relates to the field of medicines and particularly relates to a bergenin derivative as well as a preparation method and application thereof. The bergenin derivative disclosed by the invention has a structure shown in the specification, wherein R1 represents one of a benzene ring, differently-substituted phenyl and pyridine and differently-substituted pyridine and aliphatic chain. The derivative is a dihydroisocoumarin type compound; the structure has one lactonic ring and can be applied to an anticancer drug.

Description

technical field [0001] The invention relates to the field of medicine, in particular to a petracenin derivative, a preparation method and an application. Background technique [0002] Cancer is one of the serious diseases that endanger human life and health at present, and chemotherapy is still one of its main treatment methods. Since the 1990s, more than 200 anticancer drugs have been under research and development worldwide, and dozens of chemotherapy or adjuvant drugs have been used in clinical treatment, but most drugs can only alleviate the disease. Moreover, most of the existing antineoplastic drugs are chemically synthesized drugs, which have problems such as high toxicity and side effects, and easy drug resistance. Therefore, searching for high-efficiency and low-toxic natural anti-cancer tumor active compounds from nature or carrying out structural modification to synthesize their derivatives has become an important trend in the current anti-tumor drug research. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/04A61P35/00
Inventor 闫福林杨彦霞闫建伟郭兰青贾建伟尹延彦冀紫阳庄方方殷田田梁会娟
Owner XINXIANG MEDICAL UNIV
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