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5-hydroxytryptophane methyl ester derivative with anti-tumor activity and preparation method and application thereof
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A technology of hydroxytryptophan methyl ester and anti-tumor activity, which is applied in the field of 5-hydroxytryptophan methyl ester derivatives and its preparation, and can solve problems such as unsatisfactory therapeutic effect, enhanced systemic toxic and side effects, and reduced effective drug concentration.
Active Publication Date: 2016-04-13
XINXIANG MEDICAL UNIV
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At present, the main treatment method for malignant tumors is still mainly surgical treatment, supplemented by comprehensive treatment such as chemotherapy, radiotherapy, gene therapy and other biological treatments, but the treatment effect is still not satisfactory. Among them, radiotherapy and chemotherapy are extremely important non-surgical treatments. However, while radiotherapy and chemotherapy kill tumor cells, they also cause serious damage to normal cells in the body.
Due to the lack of targeting of the drug itself, the effective concentration of the drug at the tumor site is reduced, the systemic side effects are enhanced, and there are treatment problems such as low cure rate, multidrug resistance, and large toxic and side effects.
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[0017] Synthesis of 5-hydroxy-N-[[1-(4-tert-butylbenzyl)-1H-1,2,3-triazol-4-yl]carbonyl]-D-tryptophan methyl ester :
[0020] The specific steps of the synthesis process are:
[0021] 1) Synthesis of 5-hydroxytryptophan methyl ester
[0022] Add 44.00 g (0.2 mol) of 5-hydroxytryptophan and 350 mL of methanol into a 500 mL three-necked flask, cool down to -5°C, and slowly add 17.4 mL (0.24 mol) of thionylchloride dropwise at low temperature. After the dropwise addition, the temperature was raised to 35° C. to react overnight. TLC detects that the raw material disappears and stops the reaction. Methanol was distilled off under reduced pressure, and after cooling, 300 mL of ethyl acetate was added to stir, filtered with suction, and dried to obtain 43.53 g (92...
experiment example 1
[0032] The purpose of this test example is to study the in vitro anti-tumor cellproliferation activity of the compound of the present invention
[0033] Human esophageal squamous cell carcinoma cells (TE-1), human gastric carcinoma cells (MGC803), and human coloncarcinoma cells (HCT116) in the logarithmic growth phase were divided into 6×10 3 Each well was inoculated into a 96-well plate, and after 24 hours of culture, the medium was replaced with 5-hydroxy-N-[[1-(4-tert-butylbenzyl)-1H-1,2,3-triazol Azol-4-yl]carbonyl]-D-tryptophan methyl ester medium, 9 concentrations for each sample, respectively 128, 64, 32, 16, 8, 4, 2, 1, 0.5 μg / mL, A blank control group was set up, and culture continued for 72 hours. After the culture is over, add 20 μL of MTT to each well, discard the medium after four hours, add 150 mL of DMSO to each well, measure the OD value with a microplate reader at a wavelength of 490 nm after shaking evenly, and calculate the IC of the compound using SPSS s...
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Abstract
The invention discloses a 5-hydroxytryptophane methyl ester derivative with the anti-tumor activity and a preparation method and application thereof. 5-hydroxyl-N-[[1-(4-tertiary butyl benzyl)-1H-1,2,3-triazole-4-yl]carbonyl]-D-tryptophan methyl ester is specifically adopted as the 5-hydroxytryptophane methyl ester derivative, and the structural formula of the 5-hydroxytryptophane methyl ester derivative is as followed (please see the formula in the description). The invention further discloses a preparation method of the 5-hydroxytryptophane methyl ester derivative with the anti-tumor activity and application of the 5-hydroxytryptophane methyl ester derivative with the anti-tumor activity in preparation of anti-tumor drugs. Accordingly, the synthesized compound has the good in-vitro anti-tumor cellproliferation activity, the growth of TE-1 cells, the growth of MGC803 cells and the growth of HCT116 cells are all obviously inhibited, and the compound can be further developed by serving as an anti-tumor drug or a lead compound.
Description
technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to a 5-hydroxytryptophan methyl ester derivative with antitumor activity and a preparation method and application thereof. Background technique [0002] Malignant tumor is an important disease that endangers human health, and its mortality rate is the second largest disease after cardiovascular and cerebrovascular diseases. At present, the main treatment method for malignant tumors is still mainly surgical treatment, supplemented by comprehensive treatment such as chemotherapy, radiotherapy, gene therapy and other biological treatments, but the treatment effect is still not satisfactory. Among them, radiotherapy and chemotherapy are extremely important non-surgical treatments. However, while radiotherapy and chemotherapy kill tumor cells, they also cause serious damage to normal cells in the body. Due to the lack of targeting of the drug itself, the effectiv...
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