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Toad lactam compound as well as preparation method and application thereof

A technology of lactam and ester compounds, which is applied in the field of bufa lactam compounds and their preparation, can solve the problems of small safety window, paralysis and death, high toxicity, etc., and achieve the advantages of convenient equipment, good inhibitory effect, and small toxic and side effects Effect

Inactive Publication Date: 2012-03-21
JINAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But the toxicity of bufa lactones composition is bigger, and safety window is little, often because take by mistake or overdose and poisoning, poisoning symptom shows as shortness of breath, convulsion, arrhythmia and paralysis death etc. (Han Jingtian, Chen Xiaoyi, Xu Ruicheng. Toad poison Research progress on the pharmacological activity of Ling[J]. Traditional Chinese Medicine and Clinic, 2002, 2(2): 120-122.)

Method used

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  • Toad lactam compound as well as preparation method and application thereof
  • Toad lactam compound as well as preparation method and application thereof
  • Toad lactam compound as well as preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0030] (1) Preparation of cinobufagin lactam with anti-tumor activity:

[0031] Under the protection of nitrogen, cinobufagin (separated and purified by our research group and identified its structure, please refer to Tian Haiyan for the purification steps and structural identification data, Research on the Anti-tumor Active Components of Bufo Bufa, Doctoral Dissertation of China Pharmaceutical University, 2010) 0.44g (1mmol) and ammonium acetate 0.5g (6.5mmol), dissolved in 12ml of dimethylformamide (DMF), and placed in a 100ml pressure test tube, put a stirrer, nitrogen protection seal, stirring and heating in an oil bath. React at 100°C for 3 hours, and detect the end point of the reaction with TLC; after the reaction is completed, the reaction mixture is cooled to room temperature, and the solvent DMF is removed by concentrating under reduced pressure; the sample after the reaction is dissolved in methanol, and a preparative liquid phase column (waters, C18, 5 μm, 20 × 250...

Embodiment 2

[0046] (1) Preparation of 16β-hydroxybufalin lactam with anti-tumor activity:

[0047] Under the protection of nitrogen, 16β-hydroxybufalin (separated and purified by our research group and identified its structure, please refer to Tian Haiyan for the purification steps and structural identification data, research on anti-tumor active ingredients of toadstool, doctoral dissertation of China Pharmaceutical University, 2010) 0.40g (1mmol ), ammonium acetate 0.5g (6.5mmol), DMF (12ml) are placed in a 100ml pressure-resistant test tube, put a stirrer, nitrogen protection seal, stir and heat in an oil bath, react at 140 ° C for 1.5 hours, TLC The end point of the reaction was detected; after the reaction was completed, the reaction mixture was cooled to room temperature, and the solvent DMF was removed by concentration under reduced pressure. After the reaction, the sample was dissolved in methanol, separated by a preparative liquid phase column (waters, C18, 5 μm, 20 × 250mm), the...

Embodiment 3

[0056] (1) Preparation of helleboregenin lactam with anti-tumor activity:

[0057] Under nitrogen protection, helleboregenin (separated and purified by our research group and identified its structure, see Tian Haiyan for purification steps and structural identification data, research on anti-tumor active ingredients of toadstool, doctoral dissertation of China Pharmaceutical University, 2010) 0.42g (1mmol) ), ammonium acetate 0.5g (6.5mmol), DMF (12ml) is placed in the pressure-resistant test tube of 100ml, puts into a stirring bar, nitrogen protection seals, stirs and heats in oil bath. React at 120°C for 1 hour, raise the temperature to 160°C for another 0.5 hour, and detect the end point of the reaction by TLC; after the reaction is complete, cool the reaction mixture to room temperature, and concentrate under reduced pressure to remove the solvent DMF. After the reaction, the sample was dissolved in methanol, separated by a preparative liquid phase column (waters, C18, 5 μ...

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Abstract

The invention discloses a toad lactam compound as well as a preparation method and application thereof. The preparation method comprises the steps of: mixing a toad lactone compound and ammonium acetate according to molar ratio of 1: (3-8); dissolving by utilizing organic solvent; reacting at a temperature of 100-160 DEG C for 0.5-3h under the protection of inert gas; decompressing, concentrating, removing the organic solvent; separating and purifying by utilizing a preparative high performance liquid chromatography method; and obtaining the toad lactam compound. The preparation method is simple, easy to carry out, safe, reliable and higher in yield. Proved by experiments, the toad lactam compound obtained in the invention has the advantages of good antitumor effect, very strong inhibitory action on various cancer cells such as PC3, DU145, LNCaP, MCF-7 and Hela, especially much better selective inhibitory action to hormone-dependent cancer cells such as the LNCaP and the MCF-7 than the toad lactone compound and remarkably lower toxicity to normal cells than the toad lactone compound. The toad lactam compound applied in preparing antitumor drugs has the advantages of being high in efficiency and low in toxicity and meeting the requirements of drug development.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a bufolactam compound and its preparation method and application. Background technique [0002] Malignant tumors have always been a major disease threatening human health. With the change of people's diet, the deterioration of living environment and many other factors, the incidence of cancer is on the rise. Its mortality rate is second only to cardiovascular disease. At present, the main treatment methods for malignant tumors are still surgery, radiotherapy and chemotherapy. Among them, chemotherapy occupies an important position, but most of the currently used chemotherapeutic drugs have the disadvantages of high toxicity, low safety, and easy drug resistance. Studies in recent years have found that some natural products have strong anti-tumor effects, such as paclitaxel and vinblastine. However, in view of the limited structure of natural products, the struct...

Claims

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Application Information

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IPC IPC(8): C07J71/00C07J43/00A61K31/58A61P35/00
Inventor 江仁望李娟姜飞田海妍
Owner JINAN UNIVERSITY
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