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Compound N-total trans dimension methanamide derivative and its preparation method and application

A retinoic acid, all-trans technology, applied in the chemical field, can solve the problems of retinoic acid not reaching the effective inhibitory concentration, liver function damage, easy recurrence, etc., to achieve inhibition of metastasis potential, high degree of anti-malignancy, and low survival rate Effect

Inactive Publication Date: 2003-07-16
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Some studies have found that the application of retinoic acid in patients with liver cancer can not reach the effective inhibitory concentration, and it will also produce serious toxic side effects and retinoic acid syndrome, such as liver function damage, drug resistance and relapse after induction of remission, and invalid for recurrent cases, etc. , so the treatment of retinoic acid for patients with liver cancer is actually very restrictive

Method used

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  • Compound N-total trans dimension methanamide derivative and its preparation method and application
  • Compound N-total trans dimension methanamide derivative and its preparation method and application
  • Compound N-total trans dimension methanamide derivative and its preparation method and application

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Effect test

Embodiment 1

[0032] Use all-trans retinoic acid dry powder as a synthetic raw material, react with phenol and phosphorus trichloride, and stir for 2.5 hours under the protection of nitrogen, an orange-red solution appears, and a small amount of phosphorous acid precipitates on the wall of the reaction bottle. Stir under protection for 15 minutes, transfer to a dry layered funnel, separate the benzene solution that generates retinoyl chloride, stir in an ice bath for 10 minutes, add dropwise ice-cold L-proline, which has been pre-prepared Dissolve in 2mol / l sodium hydroxide solution, continue to stir, and adjust the pH of the solution with 2mol / l sodium hydroxide solution, keep it above 9.0, remove the ice bath, stir the reaction solution overnight, and divide the reaction solution into Two layers, the upper layer is brownish-yellow, the lower layer is darker in color, extracted three times with ether, the upper layer is added to a silica gel column for chromatography, samples are collected ...

Embodiment 2

[0034] Functional test of the compound of the present invention

[0035] 1. Effects on the cycle of liver cancer cells:

[0036] Hep3B liver cancer cells were treated with different concentrations, and then the cell cycle was detected by flow cytometry to observe the effect of the compound N-all-trans retinamide proline (ATRP) on the cycle of liver cancer cell Hep3B cells. The results showed that N-all Trans-retinoic acid amide proline has an effect at the beginning of 1 μmol / l, and there is a significant difference in the change of cell cycle when it is 3 μmol / l. The period of action is mainly in the G2-M phase, which increases the ratio of cells in the G2-M phase. Even liver cancer cells stay in the G2-M phase more often. Table 1 is the cell cycle analysis.

[0037] 2. Effect on the expression of Lewis antigen on the surface of liver cancer cells:

[0038]N-all-trans retinamide proline acts on Hep3B liver cancer cells for 1-3 days, and then detects and observes the expres...

Embodiment 3

[0046] The compound N-all-trans retinamide proline of the present invention was compared with all-trans retinoic acid (ATRA) and 4-aminophenol retinamide (4HPR). All-trans retinoic acid 10μM concentration acts on Hep3B cells for 3 days, 4-aminophenol retinamide and N-all-trans retinoic acid amide proline are both 3 μM on Hep3B cells for 3 days, and the cells are collected for enzyme activity. The results showed that after Hep3B liver cancer cells were treated with N-all-trans-retinamide proline for 3 days, the α-1,6FT activity increased from 150.51±68.94 in the control to 266.47±11.91pmol / hr·mg, the two groups The difference was significant (P=0.0007). However, there is no significant difference in the effects of all-trans retinoic acid and 4-aminophenol retinoic acid, indicating that the compound of the present invention has a strong regulatory effect on liver cancer cell α-1, 6FT activity, and the concentration of action is 3.3 times lower than that of ATRA , while all-tran...

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Abstract

An N-trans-vitamin A acid ethylamide derivative is prepared through reaction between trans-vitamin A acid powder, phenol and phosphorus trichloride, stirring in nitrogen gas, extracting by ether, chromatography, and mass spectroscopy. It can regulate the fucosyltransferase and suppress liver cancer cell with lower poison, so it can be used to preparing antineoplastics.

Description

technical field [0001] The invention belongs to the field of chemistry, and specifically relates to a compound N-all-trans retinoic acid derivative, a preparation method thereof and an antitumor application thereof. Background technique [0002] Retinoic acid has been used in the induction of tumor differentiation for many years, and has made great achievements in the treatment of leukemia and other tumors. The complete remission rate of promyelocytic leukemia induced by single drug reached 89%. Some studies have found that the application of retinoic acid in patients with liver cancer can not reach the effective inhibitory concentration, and it will also produce serious toxic side effects and retinoic acid syndrome, such as liver function damage, drug resistance and relapse after induction of remission, and invalid for recurrent cases, etc. , so the treatment of retinoic acid on liver cancer patients is actually very restrictive. It is known in the art that the effects of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/401A61P35/00C07D207/16
Inventor 吴兴中
Owner FUDAN UNIV
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