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Novel C8-heterocyclic alkylated purine nucleoside analogue and synthetic method thereof

A technology for heterocyclic alkylation of purine nucleosides and a synthetic method, which is applied in the fields of chemistry and medicine, and can solve the problems of expensive raw materials, complex processes, and harsh reaction conditions, and achieve the effects of easy access, avoiding reaction conditions, and mild reaction conditions

Inactive Publication Date: 2015-04-01
HENAN INST OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to solve the deficiencies in the prior art, the present invention provides a method for the synthesis of C8-position heterocycloalkylated nucleoside analogues with cheap and easy-to-obtain raw materials, mild reaction conditions, few reaction steps, and high-efficiency C-H activation. The problem of expensive raw materials, complex process and harsh reaction conditions in the compound synthesis process provides reference value for the synthesis and application of nucleoside drugs, and provides raw materials for the research of new antiviral and antitumor drugs

Method used

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  • Novel C8-heterocyclic alkylated purine nucleoside analogue and synthetic method thereof
  • Novel C8-heterocyclic alkylated purine nucleoside analogue and synthetic method thereof
  • Novel C8-heterocyclic alkylated purine nucleoside analogue and synthetic method thereof

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Effect test

Embodiment 1

[0032] Add 6-methoxy-9-benzylpurine (0.125mmol, 0.0301g) into a 25ml reaction tube, CoCl 2 ·6H 2 O (20mol%, 0.00593g), Mg 2 SO 4 (0.75mmol, 0.075g) and 2mL THF (both raw material and solvent). The reaction mixture was reacted at 50°C for 72 hours under the protection of oxygen. Track the reaction with TLC. After terminating the reaction, the reaction solution was cooled to room temperature, and the solvent was evaporated to dryness by a rotary evaporator. The resulting residue was purified by column chromatography to obtain the target compound 6-methoxy-8-(2-tetrahydrofuran)-9 -Benzyl purine, yield 85%.

Embodiment 2

[0034] Add 6-methoxy-9-benzylpurine (1.25mmol, 0.301g) to a 100ml reaction tube, CoCl 2 ·6H 2 O (20mol%, 0.0593g), Mg 2 SO 4 (7.5mmol, 0.75g) and 20mL THF (both raw material and solvent). The reaction mixture was placed in an oil bath at 70° C. and stirred for 48 hours under the protection of oxygen. Track the reaction with TLC. After terminating the reaction, the reaction solution was cooled to room temperature, and the solvent was evaporated to dryness by a rotary evaporator. The resulting residue was purified by column chromatography to obtain the target compound 6-methoxy-8-(2-tetrahydrofuran)-9 -Benzyl purine, yield 80%.

Embodiment 3

[0036] Add 6-methoxy-9-benzylpurine (12.5mmol, 3.01g) in a 500ml reaction tube, CoCl 2 ·6H 2 O (20mol%, 0.593g), Mg 2 SO 4 (75mmol, 7.5g) and 200mL THF (both raw material and solvent). The reaction mixture was stirred in an oil bath at 90°C for 48 hours under the protection of oxygen. Track the reaction with TLC. After terminating the reaction, the reaction solution was cooled to room temperature, and the solvent was evaporated to dryness by a rotary evaporator. The resulting residue was purified by column chromatography to obtain the target compound 6-methoxy-8-(2-tetrahydrofuran)-9 -Benzyl purine, yield 71%.

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Abstract

The invention discloses a novel C8-heterocyclic alkylated purine nucleoside analogue and a synthetic method thereof and provides a method for synthesizing a C8-heterocyclic alkylated nucleoside analogue by high-efficiency C-H activation. The method adopts raw materials which are easily available, and is moderate in reaction condition and few in reaction steps. The method aims to solve the problems of expensive raw materials, complex process and harsh reaction condition during synthesis of the type of compound, to provide a reference value for synthesis and application of a nucleoside medicine and to provide the raw materials for research of novel anti-virus and antitumor drugs. Meanwhile, the method disclosed by the invention provides an effective method for heterocyclic alkylatation of other nucleosides and analogues of the nucleosides and is wide in industrial application prospect.

Description

technical field [0001] The invention relates to the technical fields of chemistry and medicine, in particular to a novel C8-heterocyclic alkylated purine nucleoside analogue and a synthesis method thereof. Background technique [0002] Purine nucleoside compounds have good antiviral and antitumor activities, and thus have attracted widespread attention. C8-alkylated purine compounds have special physiological activities: for example, 8-methyladenosine has a good inhibitory effect on vaccinia virus, and 8-ethyladenosine can be used to treat respiratory syncytial virus Infection caused by 8-vinylpurine adenosine has a good effect on herpes simplex virus. When the 8-position of purine is introduced into cyclopentylamine, a series of NBTI analogues with good inhibitory effect on nucleoside transporters can be obtained. Aminoacyl tRNA synthetase is commonly used to catalyze the process of ribosomal protein conversion and almost the same type of reaction. The introduction of an ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D473/40C07D473/30C07D473/04
CPCY02P20/582C07D473/40C07D473/04C07D473/30
Inventor 牛红英苏凌云李建平郭海明王东超谢明胜渠桂荣
Owner HENAN INST OF SCI & TECH
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