N2-glycosyl-substituted 1,2,3-triazole compound and synthesis method and application thereof

A triazole compound and compound technology, applied in N2-glycosyl-substituted 1,2,3-triazole compounds and their synthesis and application fields, achieving the effects of high yield, strong inhibitory ability, and easy control of synthesis conditions

Inactive Publication Date: 2016-01-13
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] At present, 1,2,3-triazole sugar conjugates have been reported to have biological activity, but the reported 1,2,3-triazole sugar conjugates are all N1 or N3 substituted 1,2,3-triazole Azole compounds, whose synthesis is based on the [3+2] cycloaddition click reaction of terminal alkynes and organic azide compounds, 1,2,3-triazole compounds without N2-sugar group substitution, whose research is a blank

Method used

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  • N2-glycosyl-substituted 1,2,3-triazole compound and synthesis method and application thereof
  • N2-glycosyl-substituted 1,2,3-triazole compound and synthesis method and application thereof
  • N2-glycosyl-substituted 1,2,3-triazole compound and synthesis method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049]

[0050] Step 1: Compound a 1 Synthesis,

[0051] Weigh and dissolve sodium azide (8.7g, 0.13mol) in 35mL of DMSO, heat and stir, dissolve phenylnitroalkene compound (16.63g, 0.11mol) in 30mL of DMSO, and slowly drop into the stack with a constant pressure dropping funnel. In the sodium nitride solution, one drop is added dropwise at a rate of 3 seconds, and the reaction temperature is 80°C. After the dropwise addition is complete, stop heating and continue stirring, and cool to room temperature; add ammonium chloride solution to the mixed solution, extract with ethyl acetate, extract the organic phase, wash the organic layer with saturated brine again, and then wash with anhydrous sulfuric acid The organic layer was dried over sodium, filtered, and concentrated under reduced pressure to obtain a yellow-brown solid. Finally, the obtained product was washed with dichloromethane in a small amount and several times to obtain about 14.51 g of a white solid with a yield...

Embodiment 2～5

[0058] The reaction steps of embodiment 2~5 refer to step 1, step 2 and step 3 of embodiment 1, participate in the reaction compound list as follows:

[0059]

[0060] c 2 : 1 HNMR (600MHz, CDCl 3 )δ7.76–7.62(m,2H),7.57–7.51(m,1H),7.41(t,J=7.8Hz,1H),7.32(dd,J=14.4,7.3Hz,1H),5.01(s ,1H),4.85(dd,J=11.4,5.9Hz,1H),4.78–4.73(m,1H),4.69(dd,J=6.0,2.0Hz,1H),4.54–4.47(m,2H), 3.38(d, J=3.6Hz, 3H), 2.45(d, J=16.2Hz, 3H), 1.44(d, J=11.4Hz, 3H), 1.29(s, 3H).

[0061] c 3 : 1 HNMR (400MHz, CDCl 3 )δ7.68(d, J=7.8Hz, 1H), 7.37(t, J=4.2Hz, 2H), 7.27(s, 1H), 5.03(s, 1H), 4.90(d, J=6.0Hz, 1H), 4.76(d, J=7.2Hz, 1H), 4.70(d, J=6.0Hz, 1H), 4.55(dd, J=7.2, 3.0Hz, 2H), 3.39(s, 3H), 2.27( s,3H),1.48(s,3H),1.31(s,3H).

[0062] c 4 : 1 HNMR (600MHz, CDCl 3 )δ8.15(s,1H),7.83(d,J=8.4Hz,1H),7.48(s,1H),7.30(d,J=8.4Hz,1H),5.03(s,1H),4.87( d,J=6.0Hz,1H),4.79(t,J=7.2Hz,1H),4.71(d,J=6.0Hz,1H),4.62(dd,J=12.0,7.5Hz,2H),3.41( s,3H),1.47(s,3H),1.31(s,3H).

[0063] c 5 : 1 HNMR (600MHz, CDCl 3 )...

Embodiment 6

[0065]

[0066] Step 1, Step 2 and Step 3 of Embodiment 6 refer to Embodiment 1.

[0067] Step 4:

[0068] the white solid c 6 Add dilute sulfuric acid solution, stir at 80°C, react for 2 days, monitor the reaction by TLC, stop heating after the reaction is over, cool to room temperature, extract with ethyl acetate, extract the organic phase, wash the organic layer with saturated brine again, and then The organic layer was dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain a light yellow solid, and ethyl acetate / petroleum ether (1:1) column chromatography obtained a white solid. The white solid is compound d 6 .

[0069] 1 HNMR(600MHz,DMSO)δ8.14(s,1H),7.76(d,J=8.4Hz,2H),7.01(d,J=8.4Hz,2H),5.06(s,1H),4.94(d, J=6.0Hz, 1H), 4.62(dd, J=13.8, 3.2Hz, 1H), 4.47(dd, J=13.8, 8.7Hz, 1H), 4.22(d, J=6.0Hz, 1H), 4.08– 4.00(m,1H),3.41(d,J=10.2Hz,4H).

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Abstract

The invention relates to an N2-glycosyl-substituted 1,2,3-triazole compound and a synthesis method and application thereof. The general structural formula of the N2-glycosyl-substituted 1,2,3-triazole compound is shown in the specification, wherein R1 indicates H atoms or halogen atoms or alkyl groups of 1-6 carbon atoms or alkoxy groups of 3-10 carbon atoms or aryl groups or heterocyclic groups or benzoyl groups or formyloxy groups or cyano groups, and R indicates hydrogen or alkyl groups or halogen atoms or nitro groups or alkoxy groups or cyano groups and is located at ortho-position, meta-position and para-position single substitution or polysubstitution of aromatic rings. The N2-glycosyl-substituted 1,2,3-triazole compound and the synthesis method and application thereof have the advantages that synthesis conditions are easy to control, the yield is high, and the cost is low; application of triazole derivatives in the fields of pesticide, medicine, food and the like is further promoted; a new way is provided for research and development of high-value utilization and modification of triazole; the compound has high inhibiting ability for alpha-glucosidase and can be further developed into medicine used for treating or assisting in treating diabetes mellitus type 2.

Description

technical field [0001] The present invention relates to 1,2,3-triazole compound substituted by N2-glycosyl group and its synthesis method and application. Background technique [0002] 1,2,3-triazole is an important class of heterocyclic compounds, because of its special physical and chemical properties, such as the 1,2,3-triazole ring is an isostere of the amide bond, which is useful for explaining metabolism, redox And it has good stability in acid-base environment, and can participate in hydrogen bonding, etc. These properties make the triazole ring beneficial to combine with biomolecular targets, and at the same time improve the solubility of molecules, so it is widely used in agriculture, medicine, and life. Science, materials chemistry, organic synthetic chemistry and other fields have been widely used, and some 1,2,3-triazole compounds have been found to have biological activity. In medicine, a large number of 1,2,3-triazole compounds have been found to have Potentia...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/26C07H1/00A61K31/7056A61P3/10
Inventor 陈云峰张琪
Owner WUHAN INSTITUTE OF TECHNOLOGY
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