CN111454313A - Triazole glucoside derivative of 3-nitro-1-benzenesulfonyl-7-azaindole, and preparation method and application thereof - Google Patents

Triazole glucoside derivative of 3-nitro-1-benzenesulfonyl-7-azaindole, and preparation method and application thereof Download PDF

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CN111454313A
CN111454313A CN202010471912.2A CN202010471912A CN111454313A CN 111454313 A CN111454313 A CN 111454313A CN 202010471912 A CN202010471912 A CN 202010471912A CN 111454313 A CN111454313 A CN 111454313A
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azaindole
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邓莉平
罗蒙强
沈润溥
徐慧婷
席眉扬
杜奎
程凯
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Abstract

The invention belongs to the technical field of medicines, and particularly relates to a triazole glucoside derivative of 3-nitro-1-benzenesulfonyl-7-azaindole, and a preparation method and application thereof. The invention relates to a triazole glucoside derivative of 3-nitro-1-benzenesulfonyl-7-azaindole, which is specifically named as (2S,3S,4R,5S) -2- (hydroxymethyl) -6- (8 b-nitro-4-benzenesulfonyl-4, 8 b-dihydro- [1,2,3] triazole pyrrolopyridyl) -tetrahydropyran-3, 4, 5-triol.

Description

Triazole glucoside derivative of 3-nitro-1-benzenesulfonyl-7-azaindole, and preparation method and application thereof
Technical Field
The invention belongs to the technical field of medicines, and particularly relates to a triazole glucoside derivative of 3-nitro-1-benzenesulfonyl-7-azaindole, and a preparation method and application thereof.
Background
Chemical name: 3-nitro-1-benzenesulfonyl-7-azaindole, the chemical structural formula is as follows:
Figure BDA0002514557390000011
in the process of drug discovery, 7-azaindole is an important structural unit, and many natural compounds with biological activity all contain 7-azaindole structures, and people find that the structural compounds have wide application and can be used for anticancer, antibacterial, antiviral, antidepressant, hypertension treatment and the like.
The alkaloid can be directly extracted from natural animals and plants, and is used as a lead compound to carry out structural modification and modification on the alkaloid, so that a medicament with more ideal curative effect is found by analyzing the structure-activity relationship with a target spot, and the alkaloid is also a good choice.
Disclosure of Invention
The invention aims to provide a triazole glucoside derivative of 3-nitro-1-benzenesulfonyl-7-azaindole, and a preparation method and application thereof, and the specific scheme is as follows:
a triazole glucoside derivative of 3-nitro-1-benzenesulfonyl-7-azaindole, which is specifically named as (2S,3S,4R,5S) -2- (hydroxymethyl) -6- (8 b-nitro-4-benzenesulfonyl-4, 8 b-dihydro- [1,2,3] triazole pyrrolopyridyl) -tetrahydropyran-3, 4, 5-triol, the (2S,3S,4R,5S) -2- (hydroxymethyl) -6- (8 b-nitro-4-benzenesulfonyl-4, 8 b-dihydro- [1,2,3] triazole pyrrolopyridyl) -tetrahydropyran-3, 4, 5-triol has the following chemical structural formula:
Figure BDA0002514557390000012
a preparation method of triazole glucoside derivatives of 3-nitro-1-benzenesulfonyl-7-azaindole comprises the following steps:
(1) adding 1.18g of 7-azaindole and 10m L DMF (dimethyl formamide) into a 50m L round-bottom flask, slowly adding 0.6g of NaH under the ice bath condition, stirring for 10 minutes, adding 5m L of DMF solution dissolved with 1.94g of benzene sulfonyl chloride, stirring at room temperature, monitoring the reaction end point by T L C, after the reaction is finished, adding 20m L water into the reaction liquid, extracting by using ethyl acetate 20m L× 3, combining organic layers, and evaporating the solvent to dryness to obtain the N-benzenesulfonyl-7-azaindole;
(2) adding 20m L acetic anhydride into a 50m L round-bottom flask, slowly dripping 0.2m L concentrated nitric acid into the acetic anhydride under an ice bath condition, stirring for 10 minutes, directly dripping the reaction liquid into 30m L solution dissolved with the N-benzenesulfonyl-7-azaindole, stirring at room temperature overnight after dripping, monitoring the reaction end point by T L C, pouring the reaction liquid onto 50g of ice after the reaction is finished, stirring for 1 hour, extracting by using ethyl acetate 20m L× 3, combining organic layers, drying by using anhydrous sodium sulfate, evaporating the solvent to dryness, and carrying out column chromatography by using an eluent to obtain the 3-nitro-1-benzenesulfonyl-7-azaindole;
(3) introducing a galactoside triazole structure, namely mixing 3-nitro-1-benzenesulfonyl-7-azaindole and 1-azido-peracetylgalactose in methanol at room temperature to perform [3+2] dipolar cycloaddition reaction, refluxing for about 5 hours, monitoring T L C until the raw material point disappears, and removing the solvent under reduced pressure until the raw material point is dry to obtain an intermediate compound.
(4) And (2) putting the intermediate compound into a reaction bottle, adding methanol and dichloromethane for dissolving, slowly adding sodium methoxide, after dropwise adding for about half an hour, heating, condensing, refluxing and continuing to react for 3-4 hours, monitoring by T L C until the raw material point disappears, adding cation exchange resin for neutralization under stirring, adjusting the pH to 5-6, filtering, washing the ion exchange resin for several times by using methanol, decompressing the filtrate to remove the mixed solvent to obtain a yellow solid, purifying by using a V (chloroform) to V (methanol) 15:1 column chromatography, and drying in vacuum to obtain the triazole glycoside derivative of 3-nitro-1-benzenesulfonyl-7-azaindole.
The ratio of the amount of the 3-nitro-1-benzenesulfonyl-7-azaindole to the amount of the 1-azido-peracetylgalactose substance in the step (3) is 1: 1.
In the step (4), the volume ratio of the mixed solvent methanol to the dichloromethane is 3:1, and the mass ratio of the intermediate compound to the sodium methoxide is 1: 2.
And (3) eluting agent in the step (2) is V (petroleum ether) and V (ethyl acetate) which are 5: 1.
The triazole glucoside derivative of the 3-nitro-1-benzenesulfonyl-7-azaindole is applied to the antineoplastic drugs.
The application of the triazole glucoside derivative of the 3-nitro-1-benzenesulfonyl-7-azaindole in the aspect of hepatitis B virus resistance.
The 1,2, 3-triazole compound has various biological activities of resisting bacteria, tumors, tuberculosis, viruses, convulsion and the like. Because the structure of the aromatic biodegradable polyester is aromatic, the biodegradable polyester is not easy to be biodegraded; is rich in electrons, can be tightly combined with biomacromolecules through hydrogen bonds and dipole interaction, and is often used as an effective functional group to be introduced into the structure of the existing medicament so as to improve the physicochemical property and pharmacokinetic parameters of the medicament and improve the biological activity of the medicament. The glucoside compound has good antibacterial and anticancer activities. The introduction of a glucoside structure into the compound can enhance the water solubility and targeting property of the compound and improve the pharmacological property of the compound. The present invention introduces this structure.
The 1, 3-dipolar cycloaddition reaction is the most important method for synthesizing five-membered heterocyclic compounds with good regioselectivity and body selectivity, and is also a more active reaction in heterocyclic pharmaceutical chemistry research. The indole or 7-azaindole becomes an electrophilic reagent with the property similar to that of an electron-deficient olefin after connecting electron-withdrawing groups on the 3-position and the 1-position N, and the research reports on the aspect are relatively less. 7-azaindole, as a member of indole compounds, has important physiological and pharmacological activities, and reports thereof are less than that of indole. Therefore, research on 7-azaindole and in-situ generated 1, 3-dipole dearomatization cycloaddition reaction is carried out, and the construction of polycyclic 7-azaindoline skeleton derivatives is of great significance for enriching the application range of azaindole and constructing compounds with physiological activity.
Meanwhile, drug absorption requires appropriate water solubility and lipid solubility to be able to permeate the lipid bilayer of the biological membrane. The transdermal absorption of the medicine in vitro and the dissolution, absorption, distribution and transportation of the medicine in vivo are all related to the lipid-water distribution coefficient. 7-azaindole and triazole glucoside structures are combined together to obtain a more ideal lipid-water partition coefficient.
The invention provides a triazole glycoside derivative of 3-nitro-1-benzenesulfonyl-7-azaindole, namely (2S,3S,4R,5S) -2- (hydroxymethyl) -6- (8 b-nitro-4-benzenesulfonyl-4, 8 b-dihydro- [1,2,3] triazole pyrrolopyridyl) -tetrahydropyran-3, 4, 5-triol and a preparation method and application thereof, wherein the preparation method comprises the step of introducing a glycosyl triazole ring into a chemical structure of 3-nitro-1-benzenesulfonyl-7-azaindole by using a 1, 3-dipolar cycloaddition method, so that a novel 7-azaindole derivative containing a galactose triazole structure is finally synthesized. The (2S,3S,4R,5S) -2- (hydroxymethyl) -6- (8 b-nitro-4-benzenesulfonyl-4, 8 b-dihydro- [1,2,3] triazole pyrrolopyridyl) -tetrahydropyran-3, 4, 5-triol prepared by the invention has stronger tumor cell inhibition effect and in-vitro anti-hepatitis B virus activity, and provides a foundation for further application in the medical field.
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FIG. 1 is a schematic diagram of a chemical structural formula of a triazole glucoside derivative of 3-nitro-1-benzenesulfonyl-7-azaindole.
Detailed Description
The technical solutions of the present invention are further described in detail below with reference to the drawings and examples, which should not be construed as limiting the present invention.
The 7-azaindole derivatives are widely concerned as a useful intermediate and various pharmaceutical activities shown by the intermediates. The general idea of the invention is to skillfully introduce glucoside with biological activity and 1,2, 3-triazole pharmacodynamic structure into the molecular structure of 3-nitro-1-benzenesulfonyl-7-azaindole, highly specifically prepare (2S,3S,4R,5S) -2- (hydroxymethyl) -6- (8 b-nitro-4-benzenesulfonyl-4, 8 b-dihydro- [1,2,3] triazole pyrrolopyridyl) -tetrahydropyran-3, 4, 5-triol and improve pharmacological activity.
The invention relates to a triazole glucoside derivative of 3-nitro-1-benzenesulfonyl-7-azaindole, namely (2S,3S,4R,5S) -2- (hydroxymethyl) -6- (8 b-nitro-4-benzenesulfonyl-4, 8 b-dihydro- [1,2,3] triazole pyrrolopyridyl) -tetrahydropyran-3, 4, 5-triol, which has the following chemical structural formula:
Figure BDA0002514557390000051
this embodiment is a method for preparing a triazole glycoside derivative of 3-nitro-1-benzenesulfonyl-7-azaindole, i.e., (2S,3S,4R,5S) -2- (hydroxymethyl) -6- (8 b-nitro-4-benzenesulfonyl-4, 8 b-dihydro- [1,2,3] triazole pyrrolopyridinyl) -tetrahydropyran-3, 4, 5-triol (compound 6), including the steps of:
as shown in fig. 1, chemical formula 1 is 7-azaindole (compound 1), chemical formula 2 is N-benzenesulfonyl-7-azaindole (compound 2), chemical formula 3 is 3-nitro-1-benzenesulfonyl-7-azaindole (compound 3), chemical formula 4 is 1-azido-peracetyl galactose (compound 4), under mild conditions, a dipolar cycloaddition reaction is performed to generate an intermediate 5 (compound 5), the compound 5 is deacetylated to generate a compound corresponding to chemical formula 6, namely (2S,3S,4R,5S) -2- (hydroxymethyl) -6- (8 b-nitro-4-benzenesulfonyl-4, 8 b-dihydro- [1,2,3] triazolopyridyl) -tetrahydropyran-3, 4, 5-triol (Compound 6).
The specific preparation method of the compound (6) comprises the following steps:
(1) synthesizing N-benzenesulfonyl-7-azaindole, namely adding 1.18g (10mmol) of 7-azaindole (compound 1) and 10m L DMF into a 50m L round-bottom flask, slowly adding 0.6g (25mmol) of NaH under the condition of ice bath, stirring for 10 minutes, adding DMF solution 5m L in which 1.94g (11mmol) of benzenesulfonyl chloride is dissolved, stirring at room temperature, monitoring the reaction end point by T L C, adding 20m L water into the reaction solution after the reaction is finished, extracting by using ethyl acetate 20m L× 3, combining organic layers, and evaporating the solvent to obtain the N-benzenesulfonyl-7-azaindole (compound 2);
(2) adding 20m L of acetic anhydride into a 50m L round-bottom flask, slowly dripping 0.2m L of concentrated nitric acid into the acetic anhydride under an ice bath condition, stirring for 10 minutes, directly dripping the reaction liquid into 30m L of solution in which the N-benzenesulfonyl-7-azaindole is dissolved, stirring overnight at room temperature after dripping, monitoring the reaction end point by T L C, pouring the reaction liquid onto 50g of ice after the reaction is finished, stirring for 1 hour, extracting by using ethyl acetate 20m L× 3, combining organic layers, drying by using anhydrous sodium sulfate, evaporating the solvent to dryness, and carrying out column chromatography by using an eluent V (petroleum ether): V (ethyl acetate): 5:1 to obtain 3-nitro-1-benzenesulfonyl-7-azaindole (compound 3);
(3) introducing galactoside triazole structure, mixing 31.7mg (0.1mmol) of 3-nitro-1-benzenesulfonyl-7-azaindole and 37.3mg (0.1mmol) of 1-azido-peracetylgalactose (compound 4) in methanol at room temperature to perform [3+2] dipolar cycloaddition reaction, refluxing for about 5 hours, monitoring by T L C until the raw material point disappears, and removing the solvent under reduced pressure until the solvent is dried to obtain an intermediate compound 5.
(4) Adding 12m L methanol and 3m L dichloromethane into an intermediate compound 5(0.2mmo1) in a reaction bottle for dissolving, slowly adding sodium methoxide (0.98m L, 0.41 mol/L and 0.4mmo1), after dropwise adding for about half an hour, heating, condensing, refluxing and continuing to react for 3-4 hours, monitoring T L C until a raw material point disappears, adding cation exchange resin for neutralization while stirring, adjusting the pH to 5-6, filtering, washing the ion exchange resin for a plurality of times by methanol, removing a mixed solvent from a filtrate under reduced pressure to obtain a yellow solid, purifying by column chromatography with V (chloroform) to V (methanol) of 15:1, and performing vacuum drying to obtain a compound 6.
As shown in fig. 1, the triazole glycoside derivative of 3-nitro-1-benzenesulfonyl-7-azaindole with chemical structural formula 6, namely (2S,3S,4R,5S) -2- (hydroxymethyl) -6- (8 b-nitro-4-benzenesulfonyl-4, 8 b-dihydro- [1,2,3] triazole pyrrolopyridyl) -tetrahydropyran-3, 4, 5-triol, is provided.
The experimental data are as follows: (2S,3S,4R,5S) -2- (hydroxymethyl) -6- (8 b-nitro-4-benzenesulfonyl-4, 8 b-dihydro- [1,2,3] triazolopyridinyl) -tetrahydropyran-3, 4, 5-triol (Compound 6) is a pale yellow powder with a yield of 62.5%, a melting point m.p.152-153 ℃, and nuclear magnetic hydrogen spectrum, infrared spectrum and elemental analysis data as follows:
1HNMR(DMSO-d6):8.38～8.37(m，1H)，8.03(d，J＝7.6Hz，2H)，7.72(dd，J＝7.6，1.2Hz，1H)，7.57(t，J＝7.2Hz，1H)，7.45(t，J＝8.0Hz，2H),6.98(dd，J＝7.6,5.2Hz，1H)，5.56(dd，J＝6.4,3.6Hz，1H)，4.86-3.40(m,11H,7×GalactosylH,OH)；
IR(KBr)v/cm-13452,3433,2987,1712,1633,1580,1466,1212,1161,1095,755
m/e:508(100.0％)。
Anal.calcd.for C19H20N6O9S：C,44.88；H,3.96；N,16.53；found C,44.85；H,3.98；N,16.52。
in this example, the MTT method is used to determine the in vitro inhibitory effect of compound 6 on different tumor strains, and the results of the determination of the antitumor activity of (2S,3S,4R,5S) -2- (hydroxymethyl) -6- (8 b-nitro-4-benzenesulfonyl-4, 8 b-dihydro- [1,2,3] triazole pyrrolopyridinyl) -tetrahydropyran-3, 4, 5-triol (compound 6) are as follows:
compound 6 was diluted with DMSO, and tumor cells HepG2 (hepatoma cells), A375 (melanoma cells), SW620 (human colorectal adenocarcinoma cells), A549 (lung adenocarcinoma cells), SGC7901 (gastric cancer cells), SKOV3 (ovarian cancer cells) were seeded in a 96-well plate at 4000/200. mu. L/well, compound 2. mu. L was added to each well to a final concentration of 12.0. mu.M, 6.0. mu.M, 3.0. mu.M, 1.5. mu.M, together at 37 ℃ with 5% CO2The cells were incubated in an incubator for 72 hours with DMSO (1%) as a blank, and after 72 hours MTT was added to a final concentration of 0.25mg/m L and placed at 37 ℃ in 5% CO2After 4 hours in the cell incubator, the solvent was blotted, 100. mu. L DMSO was added to each well, absorbance (OD value) was measured at 570nm with an enzyme-linked immunosorbent assay, and the data obtained was used to calculate IC50The value is obtained. PickSelecting compounds with high inhibitory activity, and determining the influence of different action times of the compounds at different concentrations on the human tumor cell cycle and apoptosis.
The test compounds of different concentrations were coarse-screened in 96-well plates and IC was calculated from the resulting inhibition50Values, results are given in the table below.
TABLE 1 Compound 6(2S,3S,4R,5S) -2- (hydroxymethyl) -6- (8 b-nitro-4-benzenesulfonyl-4, 8 b-dihydro- [1,2,3]Triazole pyrrolopyridyl) -tetrahydropyran-3, 4, 5-triol) on six tumor cell lines50Value of
Figure BDA0002514557390000071
In Table 1, (2S,3S,4R,5S) -2- (hydroxymethyl) -6- (8 b-nitro-4-benzenesulfonyl-4, 8 b-dihydro- [1,2,3]IC of triazole pyrrolopyridyl) -tetrahydropyran-3, 4, 5-triol (compound 6) on six tumor cell lines50The values show that the compound 6 has stronger tumor cell inhibition effects on A375 (melanoma cells), SW620 (human colorectal adenocarcinoma cells), A549 (lung adenocarcinoma cells) and SKOV3 (ovarian carcinoma cells), and provides a foundation for further application in the medical field.
Taking HepG22.2.15 cells in the logarithmic growth phase, washing the cells for 2 times by 0.02% EDTA, digesting the cells by 0.25% trypsin, uniformly blowing the cells, and counting the number of the cells to 2.5 × 10 (cells)/m L-1And inoculated into 24-well plate at 0.5m L per well, and the administration is started after the cells are attached to the wall, and the samples are prepared into culture solution containing DMSO at 12.5, 25 and 50 mu g/m L-1Adding 3 concentrations of the above-mentioned components into 24-well culture plate, adding 0.6m L per well, adding 2 wells per concentration, using cell in which the culture solution of DMS0 is added in equal quantity instead of medicinal solution as control group, administering the medicinal solution with the same concentration on 3 th day, administering the collected cell on 6 th day, washing 2 times with Phosphate Buffer Solution (PBS), extracting with virus core particle extracting reagent, using Taqman probe to make fluorescent quantitative PCR to measure HBVDNA content in cell, calculating HBVDNA inhibition rate (control group copy number-administration group copy number)/control group copy number × 100% according to formula HBVDNA inhibition rate (%) (control group copy number-administration group copy number)/control group copy number ×%, and calculating HBVDNA replication inhibition rate of sample to cellG22.2.15 the replication of HBVDNA in cells is inhibited, and a certain dose-effect relationship is shown, the result is shown in Table 2, the compound 6 is 50 mug/m L-1The inhibition rate to HBVDNA is 79.62%, and the in vitro anti-HBV activity is better.
TABLE 2 inhibition of HBVDNA cell replication by Compound 6
Figure BDA0002514557390000081
The transdermal absorption of the medicine in vitro, the dissolution, the absorption, the distribution and the transportation of the medicine are related to the lipid-water partition coefficient, the P value of the lipid-water partition coefficient is generally considered to be too low (1ogP < -2) and the compound cannot penetrate through the lipid membrane, on the contrary, the P value is too high (1ogP >3) and the compound is difficult to release from the membrane at the other side of the cell because of strong fat solubility and enters the nearby blood vessel or lymphatic vessel, and the experimental result shows that the L ogP of the n-octanol/water partition coefficient of the compound 6 is 2.57, is more ideal and meets the principle of pharmacy.
The above embodiments are only for illustrating the technical solution of the present invention and not for limiting the same, and those skilled in the art can make various corresponding changes and modifications according to the present invention without departing from the spirit and the essence of the present invention, but these corresponding changes and modifications should fall within the protection scope of the appended claims.

Claims (7)

1. A triazole glucoside derivative of 3-nitro-1-benzenesulfonyl-7-azaindole, which is specifically named as (2S,3S,4R,5S) -2- (hydroxymethyl) -6- (8 b-nitro-4-benzenesulfonyl-4, 8 b-dihydro- [1,2,3] triazole pyrrolopyridyl) -tetrahydropyran-3, 4, 5-triol, is characterized in that the (2S,3S,4R,5S) -2- (hydroxymethyl) -6- (8 b-nitro-4-benzenesulfonyl-4, 8 b-dihydro- [1,2,3] triazole pyrrolopyridyl) -tetrahydropyran-3, 4, 5-triol, the chemical structural formula is as follows:
Figure FDA0002514557380000011
2. a method for preparing triazole glycoside derivatives of 3-nitro-1-benzenesulfonyl-7-azaindole as claimed in claim 1, comprising the steps of:
(1) adding 1.18g of 7-azaindole and 10m L DMF (dimethyl formamide) into a 50m L round-bottom flask, slowly adding 0.6g of NaH under the ice bath condition, stirring for 10 minutes, adding 5m L of DMF solution dissolved with 1.94g of benzene sulfonyl chloride, stirring at room temperature, monitoring the reaction end point by T L C, after the reaction is finished, adding 20m L water into the reaction liquid, extracting by using ethyl acetate 20m L× 3, combining organic layers, and evaporating the solvent to dryness to obtain the N-benzenesulfonyl-7-azaindole;
(2) adding 20m L acetic anhydride into a 50m L round-bottom flask, slowly dripping 0.2m L concentrated nitric acid into the acetic anhydride under an ice bath condition, stirring for 10 minutes, directly dripping the reaction liquid into 30m L solution dissolved with the N-benzenesulfonyl-7-azaindole, stirring at room temperature overnight after dripping, monitoring the reaction end point by T L C, pouring the reaction liquid onto 50g of ice after the reaction is finished, stirring for 1 hour, extracting by using ethyl acetate 20m L× 3, combining organic layers, drying by using anhydrous sodium sulfate, evaporating the solvent to dryness, and carrying out column chromatography by using an eluent to obtain the 3-nitro-1-benzenesulfonyl-7-azaindole;
(3) introducing a galactoside triazole structure, namely mixing 3-nitro-1-benzenesulfonyl-7-azaindole and 1-azido-peracetylgalactose in methanol at room temperature to perform [3+2] dipolar cycloaddition reaction, refluxing for about 5 hours, monitoring T L C until the raw material point disappears, and removing the solvent under reduced pressure until the raw material point is dry to obtain an intermediate compound;
(4) and (2) putting the intermediate compound into a reaction bottle, adding methanol and dichloromethane for dissolving, slowly adding sodium methoxide, after dropwise adding for about half an hour, heating, condensing, refluxing and continuing to react for 3-4 hours, monitoring by T L C until the raw material point disappears, adding cation exchange resin for neutralization under stirring, adjusting the pH to 5-6, filtering, washing the ion exchange resin for several times by using methanol, decompressing the filtrate to remove the mixed solvent to obtain a yellow solid, purifying by using a V (chloroform) to V (methanol) 15:1 column chromatography, and drying in vacuum to obtain the triazole glycoside derivative of 3-nitro-1-benzenesulfonyl-7-azaindole.
3. The preparation method of the triazole glycoside derivative of 3-nitro-1-benzenesulfonyl-7-azaindole as claimed in claim 2, wherein: the ratio of the amount of the 3-nitro-1-benzenesulfonyl-7-azaindole to the amount of the 1-azido-peracetylgalactose substance in the step (3) is 1: 1.
4. The preparation method of the triazole glycoside derivative of 3-nitro-1-benzenesulfonyl-7-azaindole as claimed in claim 2, wherein: in the step (4), the volume ratio of the mixed solvent methanol to the dichloromethane is 3:1, and the mass ratio of the intermediate compound to the sodium methoxide is 1: 2.
5. The preparation method of the triazole glycoside derivative of 3-nitro-1-benzenesulfonyl-7-azaindole as claimed in claim 2, wherein: and (3) eluting agent in the step (2) is V (petroleum ether) and V (ethyl acetate) which are 5: 1.
6. An application of the triazole glucoside derivative of 3-nitro-1-benzenesulfonyl-7-azaindole as claimed in claim 1 in antitumor drugs.
7. The application of the triazole glucoside derivative of 3-nitro-1-benzenesulfonyl-7-azaindole as claimed in claim 1 in resisting hepatitis B virus.
CN202010471912.2A 2020-05-29 2020-05-29 Triazole glucoside derivative of 3-nitro-1-benzenesulfonyl-7-azaindole, and preparation method and application thereof Withdrawn CN111454313A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113429446A (en) * 2021-05-13 2021-09-24 绍兴文理学院元培学院 Isoxazole derivative containing xylose triazole structure and preparation method and application thereof
CN113429445A (en) * 2021-05-13 2021-09-24 绍兴文理学院元培学院 Isoxazole derivative containing arabinose triazole structure and preparation method and application thereof
CN113444133A (en) * 2021-05-13 2021-09-28 绍兴文理学院元培学院 Isoxazole derivative containing glucose triazole structure and preparation method and application thereof

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113429446A (en) * 2021-05-13 2021-09-24 绍兴文理学院元培学院 Isoxazole derivative containing xylose triazole structure and preparation method and application thereof
CN113429445A (en) * 2021-05-13 2021-09-24 绍兴文理学院元培学院 Isoxazole derivative containing arabinose triazole structure and preparation method and application thereof
CN113444133A (en) * 2021-05-13 2021-09-28 绍兴文理学院元培学院 Isoxazole derivative containing glucose triazole structure and preparation method and application thereof

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