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Use of derivatives of 1-deoxynojiri mycin containing 1,2,3-triazoles as alpha-glucosidase inhibitors

A technology of deoxynojirimycin and glucosidase, applied in antiviral agents, drug combinations, metabolic diseases, etc., can solve the problems of differences in inhibitor enzyme levels and cell levels, difficulty in artificial synthesis, low DNJ content, etc., to achieve Easy operation, mild reaction conditions, and the effect of reducing pollution

Inactive Publication Date: 2011-08-31
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

On the one hand, due to the low content of DNJ in natural products and the difficulty of purification, and the difficulty and high cost of artificial synthesis, most of the DNJ products are crude extracts of DNJ; on the other hand, DNJ is an effective glycosidase in vitro experiments Inhibitors, but acting alone in the body, at least two membrane barriers, the plasma membrane and the endoplasmic reticulum, can reach the inhibitory site, resulting in differences between the inhibitors at the enzyme level and the cellular level

Method used

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  • Use of derivatives of 1-deoxynojiri mycin containing 1,2,3-triazoles as alpha-glucosidase inhibitors
  • Use of derivatives of 1-deoxynojiri mycin containing 1,2,3-triazoles as alpha-glucosidase inhibitors
  • Use of derivatives of 1-deoxynojiri mycin containing 1,2,3-triazoles as alpha-glucosidase inhibitors

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] (1) Synthesis of hydroxymethyl-containing aromatic triazole derivative 2a

[0045]

[0046] 2a

[0047] Add p-methylazidobenzene (119 mg, 1 mmol), propynyl alcohol (96 μL, 1.2 mmol), sodium ascorbate (20 mg, 0.1 mmol), cuprous iodide (19 mg, 0.1 mmol) to the reaction In the bottle, under the protection of nitrogen, react at room temperature for 24 hours. After TLC detection shows that the reaction is complete, add water to the reaction system, extract with ethyl acetate, wash the organic phase with water, dry over anhydrous sodium sulfate, and remove ethyl acetate by vacuum rotary evaporation. Silica gel After column separation, 114 mg of a light yellow solid was obtained, with a yield of 60%.

[0048] (2) Synthesis of triazole-containing epoxy compound 3a

[0049]

[0050] 3a

[0051] Add epichlorohydrin (390 μL, 5 mmol), TBAB (16 mg) and 50% aqueous sodium hydroxide solution (0.6 mL) into the reaction flask, stir vigorously at room temperature until completely ...

Embodiment 2

[0058] (1) Synthesis of hydroxymethyl-containing aromatic triazole derivative 2b

[0059]

[0060] 2b

[0061] Add p-fluoroazide (137 mg, 1 mmol), propynyl alcohol (96 μL, 1.2 mmol), sodium ascorbate (20 mg, 0.1 mmol), cuprous iodide (19 mg, 0.1 mmol) into the reaction flask , under the protection of nitrogen, react at room temperature for 24 hours, after TLC detection shows that the reaction is complete, add water to the reaction system, extract with ethyl acetate, wash the organic phase with water, dry over anhydrous sodium sulfate, remove ethyl acetate by vacuum rotary evaporation, silica gel column After separation, 172 mg of yellow solid was obtained with a yield of 89%.

[0062] (2) Synthesis of triazole-containing epoxy compound 3b

[0063]

[0064] 3b

[0065] Add epichlorohydrin (390 μL, 5 mmol), TBAB (16 mg) and 50% aqueous sodium hydroxide solution (0.6 mL) into the reaction flask, stir vigorously at room temperature until completely dissolved, then place i...

Embodiment 3

[0072] (1) Synthesis of hydroxymethyl-containing aromatic triazole derivative 2c

[0073]

[0074] 2c

[0075] Add p-chloroazidobenzene (154 mg, 1 mmol), propynyl alcohol (96 μL, 1.2 mmol), sodium ascorbate (20 mg, 0.1 mmol), cuprous iodide (19 mg, 0.1 mmol) into the reaction flask , under the protection of nitrogen, react at room temperature for 24 hours, after TLC detection shows that the reaction is complete, add water to the reaction system, extract with ethyl acetate, wash the organic phase with water, dry over anhydrous sodium sulfate, remove ethyl acetate by vacuum rotary evaporation, silica gel column After separation, 189 mg of reddish-brown solid was obtained, with a yield of 90%.

[0076] (2) Synthesis of triazole-containing epoxy compound 3c

[0077]

[0078] 3c

[0079] Add epichlorohydrin (390 μL, 5 mmol), TBAB (16 mg) and 50% aqueous sodium hydroxide solution (0.6 mL) into the reaction flask, stir vigorously at room temperature until completely dissolve...

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Abstract

The invention belongs to the field of chemical medicaments, particularly relates to use of derivatives of 1-deoxynojiri mycin containing 1,2,3-triazoles as alpha-glucosidase inhibitors. The derivatives of 1-deoxynojiri mycin containing 1,2,3-triazoles have the activity of inhibiting alpha-glucosidase. Therefore, the e derivatives can be used for treating diseases such as diabetes and have a quite wide application prospect.

Description

technical field [0001] The invention belongs to the field of chemical medicine, and in particular relates to the application of a 1-deoxynojirimycin derivative containing 1,2,3-triazole as an alpha-glucosidase inhibitor. Background technique [0002] The chemical name of 1-deoxynojirimycin (1-deoxynojirimycin, DNJ) is (2R, 3R, 4R, 5S)-2-(hydroxymethyl-3,4,5-trihydroxy)pyridine, which is a kind of Metabolized azasaccharides [1]. In 1976, Yagid et al. isolated DNJ for the first time from the roots of mulberry trees. DNJ also exists in other plants, microorganisms and silkworms, and mulberry has the highest content in nature. DNJ can also be obtained by chemical synthesis or semi-synthesis. Since the structure of DNJ is similar to glucose, which is equivalent to the substitution of oxygen on the pyranose ring by nitrogen, DNJ competes with glycosyl intermediates in the process of enzyme-catalyzed sugar metabolism, thus exhibiting a strong α-glucosidase Inhibitory activity [2...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/454A61P3/10A61P3/04A61P31/12C07D401/12
Inventor 杨青张雨于丹胡芳芳匡春香
Owner FUDAN UNIV
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