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Berberine derivative and use thereof

A technology for berberine and its use, which is applied in the field of berberine derivatives and their preparation, and can solve the problems of unseen effects on glioma migration and invasion, and unsatisfactory drug efficacy.

Active Publication Date: 2014-12-17
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Studies have shown that berberine can inhibit the migration and invasion of liver cancer, human tongue squamous cell carcinoma, melanoma, breast cancer, bladder cancer, etc., but there is no report on the effect on the migration and invasion of glioma
On the other hand, although berberine has inhibitory activity against certain tumors, its efficacy is not ideal

Method used

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  • Berberine derivative and use thereof
  • Berberine derivative and use thereof
  • Berberine derivative and use thereof

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Experimental program
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Embodiment Construction

[0024] 1. Synthesis and identification of 13-substituted berberine derivatives

[0025]

[0026] 1.1 Synthesis and identification of intermediate dihydroberberine (Dihydroberberine, 1b)

[0027] Intermediate 1b was prepared by reduction method.

[0028] Dry 16g (0.0162mol) was suspended in 50mL pyridine and stirred at room temperature. Add NaBH slowly 4 700 mg, when it turns into a reddish-brown clear solution, immediately add 200 mL of ice water to the reaction solution, filter to obtain intermediate 1b, which appears as a light yellow powder, and vacuum-dry at 30°C for use. ESI-MS m / z :338[M+H] + .

[0029] 1. Synthesis and identification of 1.213-decyl berberine (B7)

[0030] Bromidedecane 0.89mL (4e.q. is 4 times the molar amount of 1b), sodium iodide (NaI) 0.60g (4e.q.), anhydrous acetonitrile 20mL, placed in a sealed high-pressure reaction bottle, Reaction at 80°C for 24h. Add 1b0.34g (1mmol, 1e.q.), fill with N 2 15min, reaction 12h. Afterwards, heat and r...

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Abstract

The invention provides a compound shown in the formula (I) or a salt thereof and use of the compound and the salt, and R is C10-C18 alkyl or benzyl. The growth inhibition, growth inhibition, and invasion inhibition of the compound and the salt on malignant glioma cells are surprisingly better than that of a berberine derivative and berberine self. In addition, the compounds can be well positioned to mitochondria, so that the compounds can be used as a mitochondrial targeting drug delivery system.

Description

technical field [0001] The present invention relates to berberine derivatives and their preparation methods and uses. Background technique [0002] Malignant glioma (Malignant Glioma) is the most common primary malignant tumor in the central nervous system, accounting for 46% of intracranial tumors. Surgery is the preferred treatment method, but because of its invasive growth and no obvious boundary with normal brain tissue, surgery is difficult to remove, and the postoperative recurrence rate is as high as 96%. Even with supplementary radiotherapy and chemotherapy, the average postoperative survival period is no more than 14 months, and the prognosis is extremely poor. The incurability of malignant glioma is closely related to its strong ability of migration and invasion. Therefore, inhibiting the migration and invasion of glioma cells is extremely critical for the treatment of malignant gliomas. However, the existing treatment methods cannot effectively inhibit the migr...

Claims

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Application Information

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IPC IPC(8): C07D455/03A61K31/4375A61P35/00A61P35/04
CPCC07D455/03
Inventor 胡海燕庹珏王亚龙谢彦奇付胜楠颜光美银巍
Owner SUN YAT SEN UNIV
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