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Laminbutinyl bromooxamide derivatives with anticancer activity and composition thereof

A technology of bromoxamide and laminarin ester, which can be used in the field of drug synthesis and can solve problems such as NIK-3T3 toxicity

Active Publication Date: 2020-10-23
QINGDAO UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For example, the researchers found that the anti-tumor activity of seaweeds in the coastal area of ​​Shandong was screened. Although the extract of the green algae Ulva pore had high cytotoxic activity on human coelomoma KB cells and HT-29 cells, it was also effective on normal human cells. Cell NIK-3T3 also has greater toxicity

Method used

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  • Laminbutinyl bromooxamide derivatives with anticancer activity and composition thereof
  • Laminbutinyl bromooxamide derivatives with anticancer activity and composition thereof
  • Laminbutinyl bromooxamide derivatives with anticancer activity and composition thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0023] (1) Synthesis of 6-N,N,N-trimethyl-2-carbamic acid methyl ester hydrochloride: reflux 10mmol (2.24g) lamininine hydrochloride in thionyl chloride for 2h, add 50mmol (1.60g) Methanol, continue to reflux for 8h, evaporate the excess solvent, adjust the pH value to neutral with dilute hydrochloric acid, a white precipitate precipitates, filter, wash with ice ethanol and ether for several times, and dry in vacuum to obtain a white solid 1.62 g, yield 68.1%.

[0024] (2) Synthesis of lamininate-based bromooxamide derivatives: 29 mmol (8.19 g) of N-(5-bromo-2-hydroxyanilino) oxalyl ethyl ester was dissolved in 30 mL of absolute ethanol solution, Under ice-bath conditions, slowly dropwise added 32mmol (7.58g) of 6-N,N,N-trimethyl-2-carbamoylamide hydrochloride in anhydrous THF to maintain the reaction for 60min, The temperature was raised to 85°C and the reaction was heated for 6 hours. The pH value of the solution was adjusted to neutral with dilute hydrochloric acid, and a ...

Embodiment 2

[0027] (1) Synthesis of 6-N, N, N-trimethyl-2-carbamic acid methyl ester hydrochloride: same as Example 1, only the reflux time of lamininine hydrochloride in sulfur oxychloride is changed to 3h, the reflux reaction time after adding methanol was changed to 3h. 1.04 g of the target product was obtained with a yield of 43.7%.

[0028] (2) Synthesis of lamininic acid ester bromooxamide derivatives: with embodiment 1, only N-(5-bromo-2-hydroxyanilino) oxalyl ethyl ester and 6-N,N,N- The molar ratio of trimethyl-2-carbamoylamide hydrochloride was changed to 1:0.8, the reaction temperature was set at 35° C., and the reaction time was set at 10 h to obtain 4.68 g of the target product with a yield of 33.7%.

Embodiment 3

[0030] (1) Synthesis of 6-N, N, N-trimethyl-2-carbamic acid methyl ester hydrochloride: same as Example 1, only the reflux time of lamininine hydrochloride in sulfur oxychloride is changed to 2.4h, the reflux reaction time after adding methanol was changed to 8h. 1.36 g of the target product was obtained with a yield of 57.3%.

[0031] (2) Synthesis of lamininic acid ester bromooxamide derivatives: with embodiment 1, only N-(5-bromo-2-hydroxyanilino) oxalyl ethyl ester and 6-N,N,N- The molar ratio of trimethyl-2-carbamoylamide hydrochloride was set at 1:1, the reaction temperature was set at 85°C, and the reaction time was set at 4h. 7.17 g of the target product was obtained with a yield of 51.6%.

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Abstract

The invention discloses a laminine ester bromo oxamide derivative with anticancer activity and a composition thereof. The preparation method includes the steps of conducting backflow on laminine hydrochloride in thionyl chloride, adding methyl alcohol to conduct backflow again, steaming excess solvent, and regulating to neutral until white precipitate is dissolved out; filtering, using glacial alcohol and diethyl ether to wash, and conducting vacuum drying to obtain a white solid product; dissolving N-(5-bromine-2-hydroxyl aniline) ethyl oxalyl in an absolute ethyl alcohol solution, slowly adding drop by drop into anhydrous THF which dissolves prepared 6-N,N,N-trimethyl-2-carbamyl methylamine hydrochloride, conducting temperature reaction, and regulating the solution to neutral with dilutehydrochloric acid or a dilute hydrobromic acid solution until white precipitate is dissolved out; filtering, taking the precipitate to conduct recrystallization with ethyl alcohol, and conducting vacuum drying to obtain a target product. According to the laminine ester bromo oxamide derivative with anticancer activity and the composition thereof, through the introduction of a brominated ring structure, the cytotoxic activity of laminine to tumor cell strains in vitro can be enhanced.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis, and in particular relates to a lamininate bromooxamide derivative with anticancer activity and a composition thereof. Background technique [0002] Laminin is a non-protein amino acid extracted from plants such as brown algae and Heterozoa. It is a marine natural product with high activity and no toxic side effects. It can effectively inhibit the growth of cancer cells. Bioactive substances from marine sources, due to their unique structure, often have high toxicity while obtaining high activity. For example, the researchers found that the anti-tumor activity of seaweeds in the coastal area of ​​Shandong was screened. Although the extract of the green algae Ulva pore had high cytotoxic activity on human coelomoma KB cells and HT-29 cells, it was also effective on normal human cells. Cell NIK-3T3 also has greater toxicity. Lamininine is one of the few marine natural products with high act...

Claims

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Application Information

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IPC IPC(8): C07C233/56C07C231/14C07C227/18C07C229/26A61P35/00
Inventor 李子超李晓雯李群高琪
Owner QINGDAO UNIV
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