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Purine alanine derivative used for tumor therapy, and preparation method and application of derivative

A technology for tumor treatment and alanine, which is applied in the production of antineoplastic drugs, drug combinations, and bulk chemicals. Novelty effect

Inactive Publication Date: 2016-11-09
HENAN NORMAL UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] However, the synthesis of the above-mentioned purine amino acid derivatives has the disadvantages of complicated process and low yield (generally 10%-30%).

Method used

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  • Purine alanine derivative used for tumor therapy, and preparation method and application of derivative
  • Purine alanine derivative used for tumor therapy, and preparation method and application of derivative

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Embodiment 1

[0031] The specific reaction steps of synthetic 9-adenine-L-alanine include:

[0032] Step 1) Synthesis of N-(tert-butoxycarbonyl 1)-L-serine-lactone 2: In triphenylphosphine (Ph 3 Add anhydrous tetrahydrofuran (THF) (100mL) dropwise to P) (6.3g, 24.00mmol), stir for more than 10min at -78°C under argon atmosphere, then add diethyl azodicarboxylate (DEAD) dropwise , and the resulting solution was stirred for 10 min. The above tetrahydrofuran mixed solution was added dropwise to N-(tert-butoxycarbonyl 1)-L-serine (5 g, 24.36 mmol), and stirred for more than 20 min. The obtained solution was stirred at -78° C. for 20 min, and then further stirred at room temperature for 2.5 h. The solvent tetrahydrofuran was removed and the crude product was purified by column chromatography (ethane / ethyl acetate in a volume ratio of 3:1). Finally, recrystallization in ethyl acetate / n-hexane was further purified to obtain white solid compound 2 (2.4 g, yield 53%).

[0033] Step 2) Synthesis ...

Embodiment 2

[0039] The specific reaction steps of synthetic 9-guanine-L-alanine include:

[0040] Step 1) Synthesis of N-(tert-butoxycarbonyl 1)-L-serine-lactone 2: In triphenylphosphine (Ph 3 Add anhydrous tetrahydrofuran (THF) (100mL) dropwise to P) (6.3g, 24.00mmol), stir for more than 10min at -78°C under argon atmosphere, then add diethyl azodicarboxylate (DEAD) dropwise , The resulting solution was stirred for 10 min. The above tetrahydrofuran mixed solution was added dropwise to N-(tert-butoxycarbonyl 1)-L-serine (5 g, 24.36 mmol), and stirred for more than 20 min. The resulting solution was stirred at -78°C for 20 min. Then it was further stirred for 2.5 h at room temperature. The solvent was removed and the crude product was purified by column chromatography (ethane / ethyl acetate in a volume ratio of 3:1). Finally, further purification was carried out by recrystallization in ethyl acetate / n-hexane to obtain white solid compound 2 (2.4 g, yield 53%).

[0041] Step 2) Synthesi...

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Abstract

The invention discloses a purine alanine derivative used for tumor therapy, and a preparation method and an application of the derivative, and belongs to the technical field of synthesis of antitumor medicines. The purine alanine derivative used for tumor therapy comprises 9-adenine-L-alanine and 9-guanine-L-alanine with the respective chemical structural formulas shown in the description. The invention also discloses preparation methods of 9-adenine-L-alanine and 9-guanine-L-alanine, and an application of 9-adenine-L-alanine and 9-guanine-L-alanine in the preparation of antitumor medicines. Compared with other purine amino acid derivatives, the purine alanine derivative synthesized in the invention has the advantages of novel structure form, different substitution positions and structures, and high product yield being 40% or above.

Description

technical field [0001] The invention belongs to the technical field of synthesis of antitumor drugs, and in particular relates to a purine alanine derivative which can be used for tumor treatment, a preparation method and application thereof. Background technique [0002] Tumor has always been one of the most important problems endangering human health. At present, about 1 / 3 of the people in the world suffer from cancer, and 1 / 4 of them die from cancer. Therefore, the prevention and treatment of tumors has always been the focus of medical research. At present, the most commonly used treatment methods are radiotherapy and chemotherapy, but these methods have serious drawbacks. Radiotherapy and chemotherapy are not highly selective for disease-causing cells. While killing disease-causing cells, they also pose a great threat to normal cells. And if the surgical method is used, the cost is high and it is harmful to the living body itself, which may cause many complicated compli...

Claims

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Application Information

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IPC IPC(8): C07D473/34C07D473/18A61K31/52A61K31/522A61P35/00
CPCY02P20/55C07D473/34C07D473/18
Inventor 徐霆赵茜怡张全义孟竺杨刚刚吕中原史世会王绪洋徐存拴
Owner HENAN NORMAL UNIV
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