Glycosyl benzimidazole compound and preparation method as well as application thereof

A technology based on benzimidazole and benzimidazole, which is applied in the application field of preparing antibacterial drugs, can solve problems such as the difficulty of sugar-based nitrogen-containing heterocyclic compounds, and achieve good antibacterial activity, good water solubility, and high reaction yield Effect

Active Publication Date: 2016-06-01
杭州科本药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Such methods are limited by the complexity of sugar molecules and the diversity of nitrogen-containing heterocycles, making it difficult to efficiently obtain sugar-based nitrogen-containing heterocycles

Method used

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  • Glycosyl benzimidazole compound and preparation method as well as application thereof
  • Glycosyl benzimidazole compound and preparation method as well as application thereof
  • Glycosyl benzimidazole compound and preparation method as well as application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027]

[0028] 1. Dissolve 452 mg of 4-glucopyranose benzaldehyde and 186 mg of 4-bromo-o-phenylenediamine represented by formula (II) in 20 mL of DMF, add 5 mL of water, heat up to 80° C., and keep warm for 12 hours under magnetic stirring. After the reaction was completed, cool down to room temperature, add 30 mL of water, stir for 30 min, then add 30 mL of ethyl acetate for extraction. Use a separatory funnel to separate the liquid, add 30 mL of ethyl acetate to the aqueous phase for extraction, combine the organic phase after liquid separation, wash the organic phase with 50 mL of water 3 times, separate the liquid, add anhydrous magnesium sulfate to the organic phase to dry, filter, and spin dry the reaction solution , to obtain 587 mg of a new glycosylbenzimidazole compound represented by formula (I-1), with a yield of 95%. The compound of formula (I-1) is characterized as follows: yellow syrup, 1 HNMR (500MHz, CDCl 3 -d 6 )δ=7.97(d,J=7.8Hz,2H,ArH),7.71(s,1H,ArH),...

Embodiment 2

[0030] 1. Dissolve 452 mg of 4-glucopyranose benzaldehyde and 186 mg of 4-bromo-o-phenylenediamine represented by formula (II) in 20 mL of DMF, add 3 mL of water, heat up to 75° C., and keep warm for 14 hours under magnetic stirring. After the reaction was completed, cool down to room temperature, add 30 mL of water, stir for 30 min, then add 30 mL of ethyl acetate for extraction. Use a separatory funnel to separate the liquid, add 30 mL of ethyl acetate to the aqueous phase for extraction, combine the organic phase after liquid separation, wash the organic phase with 50 mL of water 3 times, separate the liquid, add anhydrous magnesium sulfate to the organic phase to dry, filter, and spin dry the reaction solution , to obtain 574 mg of a new glycosylbenzimidazole compound represented by formula (I-1), with a yield of 93%.

[0031] 2. Preparation of Bacterial Suspension

[0032] Under aseptic conditions, use the broth medium to activate Staphylococcus aureus and Escherichia co...

Embodiment 3

[0038]

[0039] 1. Replace 186 mg of 4-bromo-o-phenylenediamine with 142 mg of 4-chloro-o-phenylenediamine, and other conditions are the same as in Example 1. 533 mg of the new glycosyl benzimidazole compound represented by the formula (I-2) was obtained with a yield of 93%. Compound (I-2) was characterized as follows: yellow syrup, 1 HNMR (500MHz, CDCl 3 -d 6 )δ=7.97(d,J=8.8Hz,2H,ArH),7.54(s,1H,ArH),7.49(d,J=8.6Hz,1H,ArH),7.21–7.19(m,1H,ArH) ,7.00(d,J=8.8Hz,2H,ArH),5.30(t,J=8.0Hz,2H,GH),5.20–5.14(m,1H,GH),5.12(d,J=7.4Hz,1H ,GH),4.30–4.26(m,1H,GH),4.19–4.16(m,1H,GH),3.90–3.87(m,1H,GH),2.05–2.00(m,12H,AcH). 13 CNMR (126MHz, CDCl3 -d 6 )δ=170.69, 170.23, 169.52, 169.46, 162.85, 158.24, 152.58, 128.37, 128.20, 124.48, 123.24, 117.13, 98.42, 72.59, 72.06, 71.08, 68.18, 64.747–ES + ):found[M+H] + 575.1449.C 27 h 27 ClN 2 o 10 requires[M+H] + 575.1427.

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Abstract

The invention discloses a glycosyl benzimidazole compound and a preparation method as well as application thereof. The structure of the glycosyl benzimidazole compound is as shown in a formula (I), wherein R1 is selected from one of halogen and methyl. A method for preparing the glycosyl benzimidazole compound comprises: enabling 4-pyran glucose benzene formaldehyde as shown in a formula (II) and 4-substituted o-phenylendiamine as shown in a formula (III) to react in a mixed system formed by N,N-dimethyl formamide and water, thus obtaining the glycosyl benzimidazole compound as shown in the formula (I). The glycosyl benzimidazole compound has certain antibacterial activity to escherichia coli and staphylococcus aureus, especially to the escherichia coli, and can be used for preparing antibacterial agents, (all the formulas are shown in the description).

Description

(1) Technical field [0001] The invention relates to a glycosylbenzimidazole compound, its preparation method and its application in the preparation of antibacterial drugs. (2) Background technology [0002] Benzimidazole compounds have been widely used in the fields of medicine and pesticides due to their broad-spectrum biological activities. However, because most of these compounds have relatively large toxic and side effects, their safety has gradually attracted widespread attention. In recent years, there have been more and more research reports on the modification and transformation of nitrogen heterocyclic compounds with better biological activity through glycosylation. These nitrogen-heterocyclic compounds with good biological activity are not only improved in biological activity and water solubility, but also have greatly reduced toxic and side effects after being modified and modified by glycosyl groups. [0003] In recent years, the synthesis of glycosyl-modified n...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/26C07H1/00A61P31/04
CPCC07H1/00C07H15/26Y02A50/30
Inventor 杜奎徐伟明蒋善会
Owner 杭州科本药业有限公司
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