Sialic acid Neu5Ac derivative as well as preparation method and application thereof

A sialic acid and derivative technology, applied in the field of sialic acid Neu5Ac derivatives and their preparation, can solve problems such as in-depth research, achieve a wide range of applications, improve identification and binding, and have obvious application value.

Pending Publication Date: 2022-05-06
SHENZHEN INST OF ADVANCED TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The S protein plays an important role in the biological structure and pathogenic process of the new coronavirus. At present, the research on the S protein of the new coronavirus has not been in-depth, and the design and development of the sialic acid ligand molecule that can recognize and bind the new coronavirus with high affinity is still blank.

Method used

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  • Sialic acid Neu5Ac derivative as well as preparation method and application thereof
  • Sialic acid Neu5Ac derivative as well as preparation method and application thereof
  • Sialic acid Neu5Ac derivative as well as preparation method and application thereof

Examples

Experimental program
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Effect test

preparation example Construction

[0088] The preparation method of sialic acid Neu5Ac derivative specifically comprises the following steps:

[0089] Using sialic acid Neu5Ac as the starting material, the carboxyl group was protected to introduce R 5 The compound of formula I is obtained by protecting the group, and the compound of formula I is prepared by chlorination and acetylation at the same time to obtain the fully acetylated 2-chlorosugar of formula II, and the compound of formula II derives a functional side chain at the 2-position of the sugar ring through glycosylation Obtain the compound of formula III; The compound of formula III obtains the compound of formula IV after deacetylation and carboxyl protection to expose the amino and hydroxyl groups on the sugar ring; the compound of formula IV is obtained according to R 2 →R 1 →R 3 The introduction of the group is carried out in the order to obtain the compound of formula VII; the compound of formula VII is converted through side chain group (side ...

Embodiment 1

[0093] Example 1: Synthesis of customized sialic acid ligand functional molecule 1:

[0094]

[0095] Concentrated hydrochloric acid (1 mL) was dropped into methanol (100 mL), natural sialic acid Neu5Ac (10 g, 32.3 mmol) was added in batches, the reaction was stirred until the solution was clear, the reaction solution was neutralized, the solvent was evaporated, and the residue was rotary evaporated three times by adding toluene , drained to obtain the crude intermediate of formula 1-1, which was directly used in the next step reaction;

[0096] The crude product of formula 1-1 obtained in the previous step was dissolved in chloroacetyl (40 mL), stirred at room temperature until the reaction was complete, and the solvent was evaporated to obtain the crude product of formula 1-2, which was directly used in the next reaction;

[0097] The crude product of formula 1-2 obtained in the previous step and HOPEG 4 OBn (13.8g, 48.5mmol) was mixed with dry dichloromethane (60mL), si...

Embodiment 2

[0104] Example 2: Synthesis of customized sialic acid ligand functional molecule 2:

[0105]

[0106] Natural sialic acid Neu5Ac (10g, 32.3mmol) was dissolved in ethanol (100mL), potassium carbonate (5.36g, 38.8mmol) was added, stirred for 15 minutes, benzyl bromide (6.08g, 35.6mmol) was added dropwise, stirred at 50°C After 2 hours, TLC detected that the reaction was complete, and the reaction solution was spin-dried, and the residue was spin-evaporated three times with toluene, and then sucked dry to obtain the crude intermediate of formula 2-1, which was directly used in the next reaction;

[0107] The crude product of formula 2-1 obtained in the previous step was dissolved in chloroacetyl (20 mL), stirred at room temperature until the reaction was complete, and the solvent was evaporated to obtain the crude product of formula 2-2, which was directly used in the next reaction;

[0108] The crude product of formula 2-2 obtained in the previous step and HOPEG 4 OBn (13.79...

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Abstract

The invention discloses a sialic acid Neu5Ac derivative as well as a preparation method and application thereof, the structure of the derivative is shown as follows: R1 is selected from hydroxyl, methoxyl or substituted methoxyl; r2 is selected from an acetamido group, a substituted acetamido group, a benzamido group, a substituted benzamido group, an alkoxycarbonylamido group, a triazolyl group or a substituted triazolyl group; r3 is selected from a hydroxyl group, a methoxy group, a substituted methoxy group, an acetamido group, a substituted acetamido group, a sulfonamide group, a substituted sulfonamide group or a phosphamide group; a is or-(CH2) m-R4, and R4 is selected from amino, sulfydryl or azido; n is selected from 0, 1, 2, 3, 4, 5, 6 and 7; m is selected from 2, 3, 4, 5, 6, 7, 8, 9 and 10. The derivative provided by the invention not only can be combined with the S protein on the surface of the new coronavirus in a high-affinity manner, but also is endowed with wider application including detection of the new coronavirus, treatment of new coronapneumonia and the like through a derivative functional side chain.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a sialic acid Neu5Ac (N-acetylneuraminic acid, N-acetylneuraminic acid) derivative and a preparation method and application thereof. Background technique [0002] The pathogen that causes new coronary pneumonia is a new type of coronavirus, referred to as the new coronavirus. The International Committee on Taxonomy of Viruses named it SARS-Cov-2 (Severe acute respiratory syndromes coronavirus 2). The new coronavirus is a β-coronavirus. In addition to RNA, the new coronavirus also has abundant protein components, and its structural proteins include spike protein (S protein), membrane protein (M protein), envelope protein (E protein), nucleocapsid protein (N protein ), among which, the S protein mediates the invasion process of the new coronavirus to the host cell, and is the determinant of the pathogenicity, toxicity, host tropism and transmission characteristics of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/056C07H15/12C07H1/00A61P31/14G01N33/569
CPCC07H19/056C07H15/12C07H1/00A61P31/14G01N33/56983G01N2333/165
Inventor 李伟王怀雨
Owner SHENZHEN INST OF ADVANCED TECH
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