Azaglycosyl 1,2,3-triazole nucleoside compound, preparation method and applications thereof

A technology for ribavirin compounds and nucleoside compounds is applied in the field of compound preparation and achieves the effects of easy operation, high yield and mild reaction conditions

Active Publication Date: 2019-12-20
CHONGQING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The use of these nucleoside drugs can treat various diseases that endanger human health, but the long-

Method used

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  • Azaglycosyl 1,2,3-triazole nucleoside compound, preparation method and applications thereof
  • Azaglycosyl 1,2,3-triazole nucleoside compound, preparation method and applications thereof
  • Azaglycosyl 1,2,3-triazole nucleoside compound, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0038] Example 1

[0039] Preparation of intermediate compound with general formula II, its preparation method is as follows

[0040]

[0041] (1) Mix 2-oxazolidinone and sodium hydride at a molar ratio of 1:1, add N,N-dimethylformamide to fully dissolve it, and then add bromopropyne (bromopropyne) dropwise to the above reaction solution. The molar ratio to 2-oxazolidinone is 1:1), the reaction is stirred at room temperature for 0.5 and then quenched with water, the organic layer is extracted with ethyl acetate, dried and concentrated, and then separated by column chromatography (the eluent system is petroleum ether: Ethyl acetate=1:1) to obtain the compound of general formula II-1;

[0042] (2) Mix the compound of formula II-1 and sodium hydroxide at a molar ratio of 1:4, then add a 0.8:1 volume ratio of methanol and water mixed solution to dissolve, then heat the reaction solution to 60°C and stir React for 2 hours, spin dry the reaction solvent, and separate by column chromatogr...

Example Embodiment

[0045] Example 2

[0046] Prepare the substituent R in the azide compound according to the following reaction formula 1 for The intermediate compound III-1:

[0047]

[0048] The aniline compound III-1-1 is used to prepare the corresponding azide compound, which is also the intermediate compound III-1, in which the substituent R 2 The relationship with the general formula of the intermediate is shown in Table 1.

[0049] Table 1 Substituent R 1 According to R 2 Correspondence of the corresponding intermediates Ⅲ-1 in different preparations

[0050]

[0051]

[0052] The specific preparation method is as follows:

[0053] Mix the aniline of general formula III-1-1 and sodium nitrite at a molar ratio of 1:1 to 2.0, add a 10-30% aqueous hydrochloric acid solution to fully dissolve, stir and react at 0°C for 0.5-2h, and then add to the above Add 1mol / L sodium azide (NaN 3 ) Aqueous solution (the molar ratio of sodium azide to compound III-1-1 is 1.2~2.0:1), stir and react for 0.5~4h at ro...

Example Embodiment

[0054] Example 3

[0055] Prepare compound I according to the following reaction formula

[0056]

[0057] The corresponding compound I is prepared using the intermediate compound of general formula III-1, and the specific preparation method is as follows:

[0058] Mix the compound of general formula II, the compound of general formula III-1, copper sulfate pentahydrate and sodium ascorbate in a molar ratio of 1:1:0.1:0.3, and add a mixed solution of tetrahydrofuran and water to fully dissolve it (the volume of tetrahydrofuran and water) The ratio is 1:1), heat to 60~80℃ and stir for 0.5~6h, spin off the reaction solvent, and separate by column chromatography (eluent system is dichloromethane: methanol=10:1) to obtain the compound of general formula I .

[0059] In the preparation process, the molar ratio of the compound of general formula II, the compound of general formula III-1, copper sulfate pentahydrate and sodium ascorbate can be selected according to any ratio between 1:1~2:0...

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Abstract

The invention relates to an azaglycosyl 1,2,3-triazole nucleoside compound, a preparation method and applications thereof, and belongs to the field of compound preparation, wherein the azaglycosyl 1,2,3-triazole nucleoside compound has a structural general formula represented by a formula I, has good antitumor activity, belongs to a lead compound with excellent antitumor activity, can be developedand prepared into antitumor drugs in one step, and has good potential application prospects in the field of cancer treatment. The invention further provides a preparation method of the azaglycosyl 1,2,3-triazole nucleoside compound, wherein the method has characteristics of mild reaction condition, high yield, low cost, simpleness and easy operation.

Description

technical field [0001] The invention belongs to the field of compound preparation, and in particular relates to an azaglycosyl 1,2,3-ribavirin compound and a preparation method and application thereof. Background technique [0002] Nucleoside analogs are an important class of anti-metabolite drugs, whose structural composition is highly similar to natural nucleosides, and can interfere with the metabolic process of nucleoside compounds in cells (such as DNA / RNA synthesis or cell signal transduction etc.) to inhibit cell proliferation and virus replication. Numerous nucleoside analogs are currently approved for the treatment of various cancers and diseases caused by viral, bacterial, fungal or parasitic infections. The use of these nucleoside drugs can treat various diseases that endanger human health, but the long-term use of drugs also brings problems such as drug side effects and drug resistance that cannot be ignored. Therefore, discovering new nucleoside analogs with h...

Claims

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Application Information

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IPC IPC(8): C07D249/06C07C213/00C07C215/08C07D263/22A61P35/00A61K31/4192
CPCC07D249/06C07C213/00C07D263/22A61P35/00C07C215/08Y02A50/30
Inventor 夏熠张燕华刘茜林芸
Owner CHONGQING UNIV
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