Triazole glucoside, method for synthesizing same by enzyme chemical method and application thereof

A triazole glucoside and glucosidase technology, applied in organic chemistry, medical preparations containing active ingredients, sugar derivatives, etc., can solve the problems of slow development of new antifungal drugs, and achieve simple preparation methods and high product activity Good results

Inactive Publication Date: 2012-05-09
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Development of new antifungals appears to be slow relative to development of antibacterials

Method used

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  • Triazole glucoside, method for synthesizing same by enzyme chemical method and application thereof
  • Triazole glucoside, method for synthesizing same by enzyme chemical method and application thereof
  • Triazole glucoside, method for synthesizing same by enzyme chemical method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Embodiment 1 contains the glucoside synthesis of alkynyl / azide

[0049] 1.1 Preparation of glycosidase powder

[0050] Soak peach kernels or apple seeds in water for 2 hours, select intact and non-mildewed seeds, remove the skin, wash the floating water on the surface of the seeds with twice the volume of acetone, grind them with a tissue grinder in the presence of ethyl acetate, and use ethyl acetate Degreasing three times, acetone degreasing and dehydration twice. Enzyme powder is stored in a 4C freezer for future use.

[0051] 1.2 General Synthetic Method of Alkyne / Azide-Containing Glucosides

[0052]Add 0.54 g of glucose to a 25 ml egg bottle, dissolve in 1 ml of water, inject 5 ml of alkynyl / azido alcohol, 5 ml of acetonitrile, add 0.6 g of malosidase or myranosidase, seal with an inversion plug, pump vacuum, and argon Protected by a balloon, stirred at 50°C for 72 hours, filtered with silica gel, washed with methanol (5 ml X4), evaporated to remove the solvent ...

Embodiment 2

[0075] Example 2 Synthesis of galactosides containing alkynyl / azide

[0076] 2.1 General method for the synthesis of galactoside by transglycosidation

[0077] 2.5 g lactose was dissolved in 5 ml buffer solution (sodium acetate, 20 mM, pH 4.5) and propargyl alcohol was added. Add 0.1 g (900 U) of Aspergillus oryzae galactosidase to the system and stir at room temperature for 12 hours at 25°C. The reaction solution was filtered to remove enzymes and lactose, and the filtrate was vacuum-concentrated to a light yellow syrup, dissolved in methanol, adsorbed on crude silica gel, and subjected to column chromatography (ethyl acetate / methanol=15~10 / 1 or dichloromethane / methanol=5 / 1) elute. The target compound galactoside was obtained.

[0078] 2.1 Spectral data of alkyne / azide-containing galactosides

[0079] 2-Alkyne-propyl β-galactoside (3a):

[0080] white solid; [α] 26 D -30.2 (c0.71, CH 3 OH); 1 H NMR (300MHz, D 2 O) δ2.91(s, 1H), 3.53(dd, J=9.9, 8.1Hz, 1H), 3.64-3.7...

Embodiment 3

[0103] Embodiment 3 contains the synthesis of triazole glycoside

[0104] 3.1 General method for synthesizing triazole-containing glycosides

[0105] Alkyne / azide-containing glycosides (0.5 mmol), organic azide / alkyne compounds (0.6 mmol), copper sulfate (9 mg, 0.05 mmol) sodium ascorbate (20 mg, 0.1 mmol) or copper powder ( 200 mg) was added to tert-butanol / water (1:1, 4.0 ml). Stir at room temperature for 4 to 24 hours, and obtain triazole-containing glycosides by column chromatography (eluent ethyl acetate / methanol / water=12~8 / 1 / 0.2).

[0106] 3.2 Spectral data containing triazole glycosides

[0107] 11:

[0108] Colorless syrup; [α] 25 D -29.4 (c2.30, CH 3 OH); 1 H NMR (300MHz, CD 3 OD) δ3.15(t, J=7.8Hz, 1H), 3.23-3.28(m, 4H), 3.62(dd, J=11.7, 4.8Hz, 1H), 3.83(d, J=11.7, 1H), 4.32(d, J=8.1Hz, 1H), 4.72(d, J=12.3Hz, 1H), 4.92(d, J=12.3Hz, 1H), 7.26-7.37(m, 5H), 7.97(s, 1H ); 13 C NMR (75MHz, CD 3 OD) δ54.9, 62.7, 63.0, 71.6, 75.0, 77.8, 78.0, 103.6, 125.3, 129.1,...

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Abstract

The invention relates to triazole glucoside, a method for synthesizing the same and application thereof. The triazole glucoside is synthesized by a two step system and a one kettle way according to the following steps: saccharide and alcohol containing alkynyl or azido perform a glycosylation reaction under glycosidase catalysis to generate a glucoside compound containing terminal alkynyl or nitrine; and the glucoside compound containing terminal alkynyl or nitrine and organic nitrine or alkyne generate the target product, namely the triazole glucoside by addition cyclization under cuprous catalysis. The triazole glucoside can be used for preparing medicament, in particular antifungal medicament.

Description

technical field [0001] The present invention relates to triazole glucoside, its synthesis method, preparation and application. Background technique [0002] In recent decades, with the increase of immunocompromised patients, the widespread development of organ transplantation and interventional diagnosis and treatment, and the wide application of antibacterial and chemotherapy drugs, the incidence of fungal infection is increasing year by year. At the same time, the extensive use of antifungal drugs clinically has led to the rapid development of fungal drug resistance. Effective varieties of antifungal drugs, especially for systemic fungal infections, are very limited. At present, antifungal drugs mainly include the following categories according to their structure: 1) Representative drugs of polyene antifungal antibiotics include nystatin, amphotericin B, apamycin, trichostatin, etc., which are mainly used to treat deep fungus Infect. 2) imidazoles and triazoles. Among ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H15/26C12P19/58A61K31/7056A61P31/10
Inventor 林国强卢文芽
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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