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Benzylamino-substituted fatty acid derivative as well as preparation method and application thereof

A technology of fatty acid derivatives and benzyl amino, applied in the field of medicine, can solve problems such as side effects, tissue cell damage, and species reduction

Pending Publication Date: 2022-07-05
ZHONGSHAN WANHAN PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] As the morbidity and mortality of malignant tumors continue to show an upward trend, which seriously threatens human life and health, at present, the clinical treatment of malignant tumors is still dominated by surgical resection, radiotherapy and systemic chemotherapy. After the body, it is distributed to the lesion to inhibit the growth and spread of tumor cells, because it has the characteristics of quick effect and strong lethality, but the current anti-tumor drugs have low selection for tumor cells, and they also kill some tumor cells while killing tumor cells. Normal tissue cells are damaged to a certain extent, which brings a series of side effects and toxic reactions
Moreover, during the course of treatment, anti-tumor drug resistance leads to the reduction or failure of the anti-tumor effect of drugs, and even tumor cells develop resistance to such chemotherapeutic drugs, resulting in a reduction in the number and types of effective anti-tumor drugs, and the tumor Due to the variety of cell types and drug resistance of tumor cells, finding new anti-tumor drugs has become an urgent hope for drug researchers

Method used

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  • Benzylamino-substituted fatty acid derivative as well as preparation method and application thereof
  • Benzylamino-substituted fatty acid derivative as well as preparation method and application thereof
  • Benzylamino-substituted fatty acid derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1 Preparation of (R, E)-5-(benzyloxy)-2-hexylhexadec-2-enoic acid

[0048] The reaction flow is as follows:

[0049]

[0050] Specific preparation steps:

[0051] S1. Dissolve 10 g of compound I in 200 ml of chloroform, add 4.0 g of p-toluenesulfonic acid (TsOH), react at 64 ± 2 °C for 20 h, concentrate until there is no fraction, add 100 ml of dichloromethane to redissolve, wash with water until neutral, and concentrate 10g of concentrate was obtained, reconstituted with 15ml of ethyl acetate, added 75ml of n-heptane at 16°C, continued to cool to 0°C, stirred for 1 h, filtered, and the filter cake was dissolved in petroleum ether / ethyl acetate (2:1, v / v) Silica gel column chromatography was performed under the eluent system, and concentrated to obtain compound II (2.92 g).

[0052] S2. Dissolve 1.0g of compound II in 7ml of tetrahydrofuran, add 2.05ml of 2mol / l NaOH and react at 42.5±2.5°C for 87h, the reaction is complete, wash with saturated aqueous sodi...

Embodiment 2

[0054] Example 2 Preparation of (R, E)-5-(benzyloxy)-2-hexylhexadec-2-enoic acid

[0055] The specific reaction process is as follows:

[0056]

[0057] S1, mix 20 g of compound I, 19.2 g of triphenylphosphine (Ph 3 P), 9.36g of p-nitrobenzoic acid were suspended in 150ml of tetrahydrofuran, 19.9g of diisopropyl azodicarboxylate (DIAD) was added at 0°C, the addition was completed, the reaction was completed for 1.0h, the reaction was completed, and 150ml of ethyl acetate was added. , washed successively with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution, concentrated the organic phase to obtain 53.2 g of concentrate, and carried out petroleum ether / ethyl acetate system (2:1, v / v) column chromatography to obtain compound V ( 10.5g).

[0058] S2. Dissolve 10.5g of compound V in 60ml of methanol, add 4.35g of potassium carbonate and react at 37.5±2.5°C for 3.5h, the reaction is completed, adjust to neutrality with dilute hydroch...

Embodiment 3

[0061] Example 3 Preparation of (R, E)-5-(benzyloxy)-2-hexylhexadec-2-enoic acid

[0062] The specific reaction process is as follows:

[0063]

[0064] S1, mix 20 g of compound I, 19.2 g of triphenylphosphine (Ph 3 P), 9.5g of N-formyl-L-leucine were suspended in 100ml of tetrahydrofuran, 19.9g of diisopropyl azodicarboxylate (DIAD) was added at 0°C, the addition was completed, the reaction was performed for 1.5h, the reaction was completed, and concentrated The reaction solution was reconstituted by adding 120 ml of n-heptane, washed with methanol aqueous solution, and then the n-heptane phase was separated and concentrated, and the concentrate was placed in petroleum ether / ethyl acetate system (2:1, v / v) silica gel column column After separation, the fractions were concentrated to obtain compound VI (12.5 g).

[0065] S2. Dissolve 12.3g of compound VI in 55ml of tetrahydrofuran, add 38ml of 1mol / l sodium hydroxide and react at 27.5±2.5°C for 3.5h, the reaction is compl...

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Abstract

The invention belongs to the technical field of medicines, and particularly relates to a benzylamino-substituted fatty acid derivative as well as a preparation method and application thereof. The benzylamino-substituted fatty acid derivative disclosed by the invention is (R, E) 5-(benzyloxy)-2-hexylhexadecane-2-olefine acid, and is obtained by synthesizing a raw material 3-hexyltetrahydro-4-hydroxy-6-undecyl-2H-pyran-2-ketone, and the raw material has the following structural formula shown in the description. Under the test concentration of 40 [mu] M, the inhibition rate of the prepared derivative on pancreatic cancer PANC-1, head and neck cancer TCA8113 and breast cancer MCF-7 cells is up to 80% or above, the inhibition rate on liver cancer HepG2, nasopharynx cancer CNE-2, kidney cancer A498 and bladder cancer T24 cells is 70-80%, the inhibition activity on ovarian cancer SKOV3 cells can reach 65.8%, and the derivative can be applied to preparation of antitumor drugs.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a benzylamino-substituted fatty acid derivative and a preparation method and application thereof. [0002] technical background [0003] As the morbidity and mortality of malignant tumors continue to rise, it is a serious threat to human life and health. At present, the clinical treatment of malignant tumors is still dominated by surgical resection, radiotherapy and systemic chemotherapy. Among them, the use of chemical drugs to enter After the body, it is distributed to the lesion to inhibit the growth and spread of tumor cells, because it has the characteristics of quick effect and strong lethality, but the current anti-tumor drugs have low selection of tumor cells. Normal tissue cells are damaged to a certain extent, which brings a series of side effects and toxic reactions. In addition, in the course of treatment, anti-tumor drug resistance leads to the reduction...

Claims

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Application Information

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IPC IPC(8): C07C59/60C07C51/09C07C59/42C07C51/367C07D309/32C07D309/30A61P35/00
CPCC07C59/60C07C51/09C07C51/367C07D309/32C07D309/30A61P35/00C07C59/42Y02P20/55
Inventor 黄冠彬刘钰文林强王浩然杜志博
Owner ZHONGSHAN WANHAN PHARM CO LTD
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