N-azidoacetyl-D-mannosamine derivative, preparation method , and application thereof in detecting nitroreductase

A technology of azidoacetyl and mannosamine, which is applied in the preparation of sugar derivatives, sugar derivatives, sugar derivatives, etc., can solve the problem that detection is rarely reported.

Active Publication Date: 2020-05-15
INST OF CHEM CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, the effect of bio-orthogonal click reactions without catalyst catalysis on cell function and its therapeutic effect on diseases needs further research, and there is little work on the detection of compounds in vivo based on the process of glucose metabolism and bio-orthogonal click reactions. Therefore, the research on bio-orthogonal click reaction and sugar metabolism process is of great significance to the detection and labeling of polysaccharides, the identification and treatment of cancer cells, drug release, and the detection of biomolecules.

Method used

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  • N-azidoacetyl-D-mannosamine derivative, preparation method , and application thereof in detecting nitroreductase
  • N-azidoacetyl-D-mannosamine derivative, preparation method , and application thereof in detecting nitroreductase
  • N-azidoacetyl-D-mannosamine derivative, preparation method , and application thereof in detecting nitroreductase

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0071] Preparation of Compound (II-1)

[0072]

[0073] Under ice-water bath, compound (IV-1) (0.75g, 1.5mM) was dissolved in anhydrous tetrahydrofuran, and then a tetrahydrofuran solution of 1M tetrabutylammonium fluoride (1.5eq., 2.25mM) was added, and then in The reaction was stirred at room temperature for 3 hours. After the reaction was completed, the reaction was quenched with 10 mL of a saturated aqueous solution of ammonium chloride, extracted with ethyl acetate (50 mL×3), the organic layer was collected, dried over anhydrous sodium sulfate, filtered, and the solvent was removed. The crude product was purified by silica gel column chromatography, and the eluent was petroleum ether / ethyl acetate (v / v=1:2-1:3) to obtain a white solid (541 mg, 93%).

Embodiment 1

[0075] Preparation of compound (1)

[0076]

[0077] Under the protection of an ice-water bath and argon, the compound of formula (II-1) (388 mg, 1 mM) was dissolved in 15 mL of a dry mixed solution of tetrahydrofuran / dichloromethane (THF / DCM, 1:1 v / v), and then added Triethylamine (0.809g, 8mM) and N,N-diisopropylethylamine (1.034g, 8mM) were reacted for 10 minutes, and dissolved in 10mL of dry THF / DCM (1:1v / v) was added dropwise solution of benzyl 4-nitrochloroformate (862mg, 4mM). Continue to react at 0°C for 1 hour, remove the ice-water bath, return to room temperature, and react for 3 hours. After the reaction was complete, the solvent was removed, and the crude product was purified by silica gel column chromatography with petroleum ether / ethyl acetate (v / v=1:1) as the eluent to obtain a white solid (204 mg, 36%). 1 H NMR (400MHz, CD 3OD):δ8.261-8.231(d,2H),7.636-7.609(d,2H),5.999(s,1H),5.332-5.092(m,4H),4.729(s,1H),4.361-4.279( m,1H), 4.154-4.072(m,2H), 3.939(s,2H...

Embodiment 2

[0079] Preparation of compound (2)

[0080]

[0081] Under the protection of an ice-water bath and argon, the compound of formula (II-1) (388 mg, 1 mM) was dissolved in 15 mL of a dry mixed solution of tetrahydrofuran / dichloromethane (THF / DCM, 1:1 v / v), and then added Triethylamine (0.809g, 8mM) and N,N-diisopropylethylamine (1.034g, 8mM) were reacted for 10 minutes, and dissolved in 10mL of dry THF / DCM (1:1v / v) was added dropwise solution of 5-nitrofuran-2-methyl chloroformate (820 mg, 4 mM). Continue to react at 0°C for 1 hour, remove the ice-water bath, return to room temperature, and react for 3 hours. After the reaction was complete, the solvent was removed, and the crude product was purified by silica gel column chromatography with petroleum ether / ethyl acetate (v / v=1:1) as the eluent to obtain a white solid (189 mg, 34%). 1 H NMR (400MHz, CD 3 OD): δ7.63(d,1H),7.03(d,1H),5.990(s,1H),5.330-5.094(m,4H),4.730(s,1H),4.355-4.280(m,1H) , 4.152-4.080(m,2H), 3.931(s,2H),...

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Abstract

The invention discloses an N-azidoacetyl-D-mannosamine derivative, a preparation method, and application thereof. The structure of the compound is represented by formula (I), wherein R1 is selected from O, S, NH, NMe, and -CH = CH-; R3 is selected from O, S, NH, and NMe; R2 is selected from H, F, Cl, Br, I, -OH, -NH2, C1-6 alkyl, C1-6 alkoxy, -CO-C1-6 alkyl, -CO-NH-C1-6 alkyl, -COOC1-6 alkyl, aryl, aryloxy, heteroaryl, heteroaryloxy, heterocyclic, and heterocyclic oxy; m is selected from an integer of 1-4; A is selected from a group that can be eliminated or cleaved by itself after a catalyticreduction reaction between the compound represented by formula (I) and a nitro reductase; A represents an a bond or an e bond. The invention also provides a preparation method of the compound represented by formula (I) and application thereof in the detection of nitroreductase.

Description

technical field [0001] The invention relates to N-azidoacetyl-D-mannosamine derivatives and their preparation methods and applications, in particular to the use of N-azidoacetyl-D-mannosamine derivatives in the detection of nitroreductase (NTR) Applications. Background technique [0002] In eukaryotic cells, polysaccharides participate in the construction of cell membranes and play an important role in cell information exchange and interaction. However, polysaccharides in cells have different molecular structures, and there are certain difficulties in their labeling and functional research. Some non-natural sugars chemically modified can express polysaccharides on the cell membrane through the carbohydrate metabolism process of cells, thus providing a new method for the study of polysaccharide functions. The bioorthogonal click reaction that does not require catalysts such as cuprous ions is becoming a safe and effective method for cell labeling and detection due to its hi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H13/04C07H13/12C07H1/00G01N21/64
CPCC07H13/04C07H13/12G01N21/6428G01N2021/6432
Inventor 杨国强鲁凤仙胡睿王双青郭旭东
Owner INST OF CHEM CHINESE ACAD OF SCI
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