Benzocoumarin chalcone neuraminidase inhibitor and preparation method and application thereof

A technology of neuraminidase and benzocoumarin, applied in antiviral agents, organic chemistry, etc., can solve the problems of complex synthesis process and expensive raw materials for Tamiflu production, and achieve simple synthesis method and neuraminidase inhibition active effect

Active Publication Date: 2020-08-14
ZHEJIANG JIANFENG PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently the most widely used anti-influenza drug is Tamiflu, but with the widespread use of the drug, drug resistanc...

Method used

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  • Benzocoumarin chalcone neuraminidase inhibitor and preparation method and application thereof
  • Benzocoumarin chalcone neuraminidase inhibitor and preparation method and application thereof
  • Benzocoumarin chalcone neuraminidase inhibitor and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] A preparation method of benzocoumarin chalcone neuraminidase inhibitor, its structural formula is as shown in formula 1:

[0030]

[0031] Concrete synthetic steps are as follows:

[0032] (1) Accurately weigh 5.5g (50mmol) of resorcinol in a 50ml round bottom flask, add 15ml of 2,4-dioxane, stir and dissolve in an ice bath, then slowly add 2ml of concentrated sulfuric acid dropwise, and then use Add 7ml (55mmol) ethyl acetoacetate dropwise to the constant pressure dropping funnel. After the dropwise addition, take out the round-bottomed flask, place it in a constant temperature oil bath at 60°C, heat and stir for 4 hours, take it out, pour the reaction solution into 100ml of ice water and stir for 30 minutes, and let stand to precipitate a large amount of precipitate. After filtering, the filter cake was washed several times with a large amount of ice water, dried in a vacuum oven, and recrystallized from methanol to obtain the intermediate formula II.

[0033] (2...

Embodiment 2

[0041] A preparation method of a benzocoumarin-chalcone neuraminidase inhibitor, whose structural formula is as follows, prepared by a method similar to Example 1.

[0042] (Z)-8-(3-Hydroxy-4-nitrobenzylidene)-4-methyl-2H-furo[2,3-h]methylene-2,9(8H)-dione

[0043]

[0044]Yellow solid, 58% yield, IC 50 The value is 0.045 μM.

[0045] 1 H NMR (500MHz, CDCl 3 :F 3 CCOOD=3:2)δ8.23(ddd,J=22.5,8.6,2.0Hz,2H),7.88(d,J=1.9Hz,1H),7.56(td,J=6.0,2.9Hz,2H), 7.13(s,1H),6.57(s,1H),2.63(s,3H).

[0046] 13 C NMR (125MHz, CDCl 3 :F 3 CCOOD=3:2)δ182.59,168.68,163.24,156.25,154.47,150.10,148.45,139.96,135.83,133.82,125.65,123.66,122.53,117.52,115.27,113.01,1110.86

Embodiment 3

[0048] A preparation method of a benzocoumarin-chalcone neuraminidase inhibitor, whose structural formula is as follows, prepared by a method similar to Example 1.

[0049] (Z)-8-(4-Hydroxy-3-nitrobenzylidene)-4-methyl-2H-furo[2,3-h]methylene-2,9(8H)-dione

[0050]

[0051] Yellow solid, 55% yield, IC 50 The value is 0.85 μM.

[0052] 1 H NMR (501MHz, DMSO-d 6 )δ8.53(s,1H),8.17(d,J=7.9Hz,2H),7.53(s,1H),7.26(d,J=8.6Hz,2H),7.07(s,1H),6.42( s,1H),2.48(s,3H). 13 C NMR (126MHz, CDCl 3 :F 3 CCOOD=3:2) δ182.47, 168.29, 163.47, 156.66, 156.38, 150.11, 146.73, 140.65, 135.22, 133.68, 129.00, 124.00, 121.03, 117.49, 115.24, 112.96, 1110.76

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Abstract

The invention relates to the technical field of biological medicines. The invention relates to a benzocoumarin chalcone neuraminidase inhibitor and a preparation method and application thereof, and the inhibitor has a structure shown as a formula I. The compound is novel in structure, and experiments show that the compound has good neuraminidase inhibition activity and is expected to be used for preparing medicines for inhibiting neuraminidase activity.

Description

technical field [0001] The invention relates to the technical field of biomedicine, in particular to a benzocoumarin-chalcone neuraminidase inhibitor and a preparation method and application thereof. Background technique [0002] Neuraminidase is one of the important targets in the research and development of anti-influenza virus drugs. Anti-influenza drugs developed with neuraminidase as the target can be divided into the following categories according to their structures: cyclohexenes, pyrans, pyrrolidines Classes, benzoic acid derivatives and natural products, etc. Tamiflu is the most widely used anti-influenza drug at present, but with the widespread use of the drug, drug resistance also appears, and the raw materials of Tamiflu are extremely expensive and the synthesis process is complicated. Therefore, it is imminent to develop new neuraminidase inhibitors, especially neuraminidase inhibitors with better inhibitory effect. Contents of the invention [0003] In orde...

Claims

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Application Information

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IPC IPC(8): C07D493/04A61P31/16
CPCA61P31/16C07D493/04
Inventor 程利平钟志坚傅世凯李孟庞婉余微石林
Owner ZHEJIANG JIANFENG PHARM CO LTD
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