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1,3-bis(beta-amino acrylate) substituted imidazole compound as well as preparation method and application thereof

A technology of amino acrylates and compounds, applied in organic chemistry, drug combinations, antibacterial drugs, etc., can solve the problems of multi-step synthesis operations and low atom utilization, and achieve good functional group compatibility, cheap and easy-to-obtain catalysts, The effect of excellent yield

Active Publication Date: 2020-06-05
GUANGZHOU UNIVERSITY
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  • Abstract
  • Description
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  • Application Information

AI Technical Summary

Problems solved by technology

However, the multi-step synthesis operation is cumbersome, the atom utilization rate is low, and an equivalent or excess amount of base is required to realize the functionalization of the nitrogen atom in the imidazole structure.

Method used

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  • 1,3-bis(beta-amino acrylate) substituted imidazole compound as well as preparation method and application thereof
  • 1,3-bis(beta-amino acrylate) substituted imidazole compound as well as preparation method and application thereof
  • 1,3-bis(beta-amino acrylate) substituted imidazole compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Synthesis of 1,3-two (β-aminoacrylate) substituted imidazole compounds shown in formula I-1:

[0035]

[0036] Under nitrogen protection, 3-((3,4-dimethoxyphenethyl)imino)-2-phenylacrylate methyl ester Ⅱ-1 (101.7mg, 0.30mmol), 2- Mercaptobenzimidazole III-1 (7.5mg, 0.05mmol), catalyst [DABCO] (1.7mg, 0.015mmol) and solvent CH 3 CN (1.0 mL). After the reaction solution was stirred at 70° C. for 1 h, TLC detected that the raw materials were basically reacted, and the reaction was stopped. The reaction solution was subjected to direct column chromatography with eluent (petroleum ether / ethyl acetate=5 / 1) to obtain 38.1 mg of product I-1 as a white solid with a yield of 92%.

[0037] The analytical data of 1,3-bis(β-aminoacrylate) substituted imidazole compounds shown in formula I-1: 1H NMR (500MHz, CDCl 3):δ2.11-2.18(m,2H),2.58-2.67(m,4H),3.07-3.12(m,2H),3.632(s,6H),3.634(s,6H),3.88(s,6H ),6.35-6.39(m,4H),6.58(dd,J=8.5,2.0Hz,2H),6.75(d,J=8.0Hz,2H),6.83-6.90(m,8H),7.0...

Embodiment 2

[0039] Synthesis of 1,3-two (β-aminoacrylate) substituted imidazole compounds shown in formula I-2:

[0040]

[0041] Under nitrogen protection, 3-((4-methoxyphenethyl)imino)-2-methyl phenylacrylate II-2 (92.7mg, 0.30mmol), 2-mercaptobenzo Imidazole III-1 (7.5mg, 0.05mmol), catalyst [DABCO] (3.4mg, 0.03mmol) and solvent CH 3 CN (5.0 mL). After the reaction solution was stirred at 50° C. for 5 h, TLC detected that the raw materials had basically reacted, and the reaction was stopped. The reaction solution was subjected to direct column chromatography, eluent (petroleum ether / ethyl acetate=5 / 1), and 36.9 mg of white solid of product I-2 was obtained, with a yield of 96%.

[0042] The analytical data of 1,3-bis(β-aminoacrylate) substituted imidazole compounds shown in formula I-2: 1 H NMR (400MHz, CDCl 3 ):δ2.13-2.23(m,2H),2.62-2.66(m,4H),2.98-3.05(m,2H),3.63(s,3H),3.64(s,3H),3.80(s,3H ),3.81(s,3H),6.59-6.63(m,2H),6.77-6.81(m,10H),6.92-6.97(m,6H),7.06(brs,4H),8.93-8.95(m,...

Embodiment 3

[0044] Synthesis of 1,3-two (β-aminoacrylate) substituted imidazole compounds shown in formula I-3:

[0045]

[0046] Under nitrogen protection, 3-((4-methylphenethyl)imino)-2-methyl phenylacrylate II-3 (73.3mg, 0.25mmol), 2-mercaptobenzimidazole Ⅲ-1 (7.5mg, 0.05mmol), catalyst [Et 3 N] (1.0 mg, 0.01 mmol) and the solvent DMF (0.5 mL). After the reaction solution was stirred at 80° C. for 2.5 h, TLC detected that the raw materials were basically reacted, and the reaction was stopped. The reaction solution was subjected to direct column chromatography with eluent (petroleum ether / ethyl acetate=5 / 1) to obtain 34.6 mg of product I-3 as a white solid with a yield of 94%.

[0047] The analytical data of 1,3-bis(β-aminoacrylate) substituted imidazole compounds shown in formula I-3: 1 H NMR (400MHz, CDCl 3 ): δ2.15-2.24(m,2H),2.34(s,6H),2.65(t,J=6.0Hz,4H),2.99-3.06(m,2H),3.63(s,6H),6.60- 6.62(m,2H),6.75-6.76(m,6H),6.92-6.94(m,6H),7.05-7.07(m,8H),8.93-8.95(m,2H); 13 C NMR (10...

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Abstract

The invention belongs to the field of high polymer materials, and discloses a 1,3-bis(beta-amino acrylate) substituted imidazole compound as well as a preparation method and application thereof. The structure of the compound is shown in the specification. The 1,3-bis(beta-amino acrylate) substituted imidazole compound has a certain antibacterial property, oxidation resistance, an anti-inflammatoryeffect, an anti-parasitic effect, and the like. Therefore, the compound is expected to be developed into novel antibacterial drugs, anti-inflammatory and analgesic drugs, anti-parasitic drugs and free radical scavengers. The preparation method of the 1,3-bis(beta-amino acrylate) substituted imidazole compound has the advantages that raw materials and the catalyst are cheap and easy to obtain; thereaction conditions are mild, and the operation is simple and convenient. The substrate range is wide, the functional group compatibility is good, and a high yield of a series of 1,3-bis(beta-amino acrylate) substituted imidazole products is achieved.

Description

technical field [0001] The invention belongs to the field of polymer materials, in particular to a 1,3-bis(β-aminoacrylate) substituted imidazole compound and its preparation method and application. Background technique [0002] Imidazole compounds are a class of important biologically active molecules, such as antibacterial, antioxidant, anti-inflammatory, anti-parasitic, etc., so they have broad application prospects in the field of medicine. For example, compound A is benomyl, which is widely used in the field of pesticide and medicine, and it is a highly effective antibacterial drug. Compound B is an effective antithyroid drug. Compound C has strong antioxidant activity. Therefore, imidazole compounds have attracted extensive attention in the fields of synthetic chemistry, medicinal chemistry, and biology. Since the substituent on the nitrogen atom in the imidazole ring has an important influence on the drug activity of the whole molecule, many 1,3-disubstituted imida...

Claims

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Application Information

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IPC IPC(8): C07D235/28A61P31/04A61P29/00A61P33/00A61P39/06
CPCA61P29/00A61P31/04A61P33/00A61P39/06C07D235/28
Inventor 刘运林罗健陈国术
Owner GUANGZHOU UNIVERSITY
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