Amino acid derivative bithiazole-tryptamine anticancer compound and application

An amino acid, bithiazole technology, applied in organic chemistry, anti-tumor drugs, drug combinations, etc., can solve the problems of destruction of tissues, organ structure and function, necrosis and bleeding complicated by infection, etc., to achieve good anti-cancer effect, broad market prospects and Scientific value, simple route effect

Active Publication Date: 2021-03-30
YANTAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, malignant tumors can also destroy the structure and function of tissues and organs, ca

Method used

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  • Amino acid derivative bithiazole-tryptamine anticancer compound and application
  • Amino acid derivative bithiazole-tryptamine anticancer compound and application
  • Amino acid derivative bithiazole-tryptamine anticancer compound and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Compound (3) of Example 1

[0031] Step: 4mmol Boc-L-Ala-COOH and 4mmol pentafluorophenyl diphenyl phosphate were dissolved in 80ml dichloromethane, after stirring at room temperature for 10min, 10mmol triethylamine, 8mmol triphenylphosphine and 1mmol disulfide azide Compound 2 was added to the reaction system in sequence, and heated to reflux until the reaction was monitored by TLC; after the reaction system was cooled to room temperature, 10 mmol of bromotrichloromethane and 12 mmol of 1,8-diazabicyclodeca were slowly added to the system One-carb-7-ene (DBU), continue to react at room temperature for 1 hour, add saturated ammonium chloride solution to quench the reaction, extract with dichloromethane, combine the organic phases, dry over anhydrous sodium sulfate, and remove the solvent by rotary evaporation to obtain a brown viscous The thick liquid was separated by column chromatography to obtain the target thiazole compound 3 with a yield of 78%. [α] D 20 -36.4(c...

Embodiment 2

[0032] Example 2 compound (5)

[0033] Step: 0.5mmol of compound 3 was dissolved in 10ml of a mixture of methanol and tetrahydrofuran (volume ratio 1:1), under ice water conditions, 5ml of 0.5N sodium hydroxide solution was added to the system, and TLC was monitored until the reaction was complete. Under water conditions, carefully add 0.5N hydrochloric acid solution to the system to adjust the pH value to 2-3, extract three times with ethyl acetate, combine the organic phases, dry over anhydrous sodium sulfate, spin dry, and directly use in the next reaction. Dissolve the prepared carboxylic acid and 0.5 mmol of pentafluorophenyl diphenyl phosphate in 10 ml of dichloromethane, stir at room temperature for 10 min, then dissolve 1.5 mmol of triethylamine, 1.5 mmol of triphenylphosphine and 0.125 mmol of disulfide azide Compound 2 was added to the reaction system in sequence, heated to reflux until the reaction was monitored by TLC; after the reaction system was cooled to room t...

Embodiment 3

[0034] Example 3 compound (7)

[0035] Steps: Dissolve 0.5mmol of compound 5 in 10ml of a mixture of methanol and tetrahydrofuran (1:1), add 5ml of 0.5N sodium hydroxide solution to the system under ice water conditions, and monitor by TLC until the reaction is complete. Next, carefully add 0.5N hydrochloric acid solution to the system to adjust the pH value to 2-3, extract three times with ethyl acetate, combine the organic phases, dry over anhydrous sodium sulfate, and spin dry, then directly use in the next reaction. Dissolve the prepared carboxylic acid and 0.5 mmol of pentafluorophenyl diphenyl phosphate in 10 ml of dichloromethane, stir at room temperature for 10 min, then dissolve 1.5 mmol of triethylamine, 1.5 mmol of triphenylphosphine and 0.125 mmol of disulfide azide Compound 2 was added to the reaction system in sequence, heated to reflux until the reaction was monitored by TLC; after the reaction system was cooled to room temperature, 2.0 mmol of bromotrichloromet...

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PUM

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Abstract

The invention discloses an amino acid derivative bithiazole tryptamine compound and the application thereof. The amino acid derivative bithiazole tryptamine compound disclosed by the invention can inhibit colon cancer cell line HCT116, gastric cancer cell line MKN45, non-small cell lung cancer cell line A549 and drug-resistant oral cancer cell line KBV drugs, i.e., preparation of antitumor drugs.The synthetic method provided by the invention is simple in route and high in product purity, and can meet large-scale preparation requirements. The amino acid derivative bithiazole tryptamine compound with the anti-cancer activity has a good anti-cancer effect, has a remarkable inhibition effect on colon cancer, gastric cancer and lung cancer, particularly has an inhibition effect similar to thatof commercially available broad-spectrum anti-cancer drug doxorubicin (DOX) on a drug-resistant oral cancer cell line KBV, and can be applied to the field of tumor resistance.

Description

technical field [0001] The present invention relates to a class of amino acid derived bithiazole-tryptamine compounds with anticancer activity, including pharmaceutically acceptable salts, solvates and prodrugs thereof, as well as the preparation method and application of such compounds, belonging to the field of medicinal chemistry. Background technique [0002] Tumor refers to a local mass formed by the abnormal proliferation of cells in local tissues under the action of various tumorigenic factors. Benign tumors are easy to remove, generally do not metastasize or recur, and only squeeze and block organs and tissues. However, malignant tumors can also destroy the structure and function of tissues and organs, cause necrosis, hemorrhage and infection, and the patient may eventually die due to organ failure. When a cell in the body mutates, it divides continuously without the body's control, eventually forming cancer. All organs in the human body are composed of cells. Cel...

Claims

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Application Information

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IPC IPC(8): C07D417/14C07D417/12A61K31/427A61P35/00
CPCA61K31/427A61P35/00C07D417/12C07D417/14
Inventor 刘义王洪波刘妍杰
Owner YANTAI UNIV
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