A kind of gold triazole compound and its preparation method and application

A compound, the technology of triazole gold, applied in the field of triazole gold compounds and the preparation thereof, can solve the problems of large-scale parallel synthesis of triazole compounds, producing false positives or false negatives, unable to become building units, etc., and achieves strong water solubility. , the effect of easy availability of raw materials and mild reaction conditions

Active Publication Date: 2017-12-15
SHANDONG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since the 1,2,3-triazole compounds synthesized by click chemistry have no active reaction sites, they can only be used as linking groups and cannot become building blocks, so triazole compounds cannot be used as combinatorial chemical compounds. Large-scale parallel synthesis of units; in the Huisgen azide-alkyne cycloaddition reaction, Cu(I) is also needed as a catalyst, which is very easy to cause some groups such as boronic acid groups to produce similar Suzuki coupling reactions and was cut off
In addition, Cu(I) is difficult to remove, there may be a certain amount of residue in the final product, and Cu(I) itself has certain cytotoxicity, which makes the activity test of the final product very likely to produce false positive or false negative results
The above shortcomings make the use of click chemistry to synthesize triazole compounds have certain limitations in medicinal chemistry research.

Method used

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  • A kind of gold triazole compound and its preparation method and application
  • A kind of gold triazole compound and its preparation method and application
  • A kind of gold triazole compound and its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0033] Ph 3 PAuCl was dissolved in dry dichloromethane, an equimolar amount of silver salt was added, and stirred at 10°C for 3 minutes. The mixed solution was filtered through a short column of diatomaceous earth to remove insoluble matter to obtain a clear solution, which was then added dropwise to 2-(1,3-diphenylprop-2-yn-1-yl)-4- In the dichloromethane solution of phenyl-2H-1,2,3-triazole, it stirred at 25 degreeC for 1 hour. Concentrate the solution with a rotary evaporator, then add n-hexane, a white precipitate appears, and filter to obtain a white solid, which is further recrystallized with a 2:1 dichloromethane:n-hexane solution to obtain white crystal 1 with a yield of 90.1%. 1 H NMR (600MHz, CDCl 3 ): δ8.33-8.37(m, 4H), 8.09(d, J=7.8Hz, 2H), 7.47-7.57(m, 24H), 6.21(s, 2H); 13 CNMR (150MHz, CDCl 3 ): δ167.4, 150.0, 145.2, 134.15, 134.06, 133.8, 131.8, 131.1, 130.6, 129.7, 129.44, 129.42, 129.38, 129.31, 129.25, 128.8, 128.6, 128.1, 126.7, 5; 31 P NMR (242.7MHz, ...

Embodiment 2

[0037] Ph 3 PAuCl was dissolved in dry dichloromethane, 2 times the molar amount of silver salt was added, and stirred at 20°C for 20 minutes. The mixed solution was filtered through a short column of diatomaceous earth to remove insoluble matter to obtain a clear solution, which was then added dropwise to 2-(1,3-diphenylprop-2-yn-1-yl)-4- In the dichloromethane solution of phenyl-2H-1,2,3-triazole, it stirred at 30 degreeC for 2 hours. Concentrate the solution with a rotary evaporator, then add n-hexane, a white precipitate appears, filter to obtain a white solid, and further recrystallize with a 2:1 dichloromethane:n-hexane solution to obtain white crystal 1, and obtain a white powder with a yield of 88.1 %. 1 HNMR (600MHz, CDCl 3 ): δ8.35-8.38(m, 4H), 8.07(d, J=7.8Hz, 2H), 7.45-7.58(m, 24H), 6.11(s, 2H); 13 C NMR (150MHz, CDCl3 ): δ167.2, 150.1, 145.1, 134.35, 134.16, 133.7, 131.8, 131.0, 130.5, 129.6, 129.43, 129.4, 129.39, 129.33, 129.26, 128.8, 128.7, 128.0, 111.6, 1...

Embodiment 3

[0041] Ph 3 Dissolve PAuCl in dry dichloromethane, add 3 times molar amount of silver salt, and stir at 40°C for 30 minutes. The mixed solution was filtered through a short column of diatomaceous earth to remove insoluble matter to obtain a clear solution, which was then added dropwise to 2-(1,3-diphenylprop-2-yn-1-yl)-4- In the dichloromethane solution of phenyl-2H-1,2,3-triazole, it stirred at 20 degreeC for 1.5 hours. Concentrate the solution with a rotary evaporator, then add n-hexane, a white precipitate appears, filter to obtain a white solid, and further recrystallize with a 2:1 dichloromethane:n-hexane solution to obtain a white crystal 1, and obtain a white powder with a yield of 88.1 %. 1 H NMR (400MHz, CDCl 3 ):δ8.34(m,4H),7.96(d,J=8.2Hz,2H),7.56-7.48(m,21H),7.30(d,J=8.0Hz,2H),6.14(s,2H) ,2.38(s,3H); 13 C NMR (101MHz, CDCl 3 ):δ167.33,144.93,134.12,133.98,131.81,131.78,131.04,130.55,130.16,129.72,129.37,129.26,129.18,128.64,128.56,128.55,128.48,127.97,123.90,5...

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Abstract

The invention discloses a triazole gold compound as well as a preparation method and application thereof. The structural general formula of the compound is shown as the description, wherein R1 is phenyl, p-methylphenyl, p-Chlorophenyl, a methoxyl group, methoxycarbonyl or p-fluorophenyl; R2 is triphenylphosphine, dimethyl -phenyl phosphine, 35 fluorine Phenyl phosphine or triethylphosphine; R3 is hydrogen, methyl or phenyl; R4 is hydrogen, methyl or phenyl; X is boron tetrafluoride negative ions or trifluoromethyl sulfonic acid negative ions. The inhibitory activity IC50 of the triazole gold compound disclosed by the invention (in nanomoles) indicates that the triazole gold compound is strongly combined with thioredoxin reductase active centers. The triazole gold compound disclosed by the invention has high anticellularity reproductive activity, is a thioredoxin reductase inhibitor adopting a novel structure, is good in physico-chemical property, is good in water solubility, and can be utilized as a lead compound of antitumor drugs.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis, and relates to a gold triazole compound, a preparation method and application thereof. Background technique [0002] Thioredoxin reductase (TrxR) is a NADPH-dependent dimeric selenase containing FAD domain, which belongs to the family of pyridine nucleotide-disulfide oxidoreductases. Together with thioredoxin and NADPH, it constitutes the thioredoxin system. TrxR has a variety of biological activities, can regulate the redox reaction of the body, and promote the growth and reproduction of cells. Many tumor cells highly express TrxR, and TrxR has a certain correlation with drug resistance of tumor cells: TrxR can maintain the stability of redox in the internal environment, and can defend against oxidative stress and cell mutation, promote cell growth, and inhibit cell apoptosis. Once normal cells are transformed into cancer cells, TrxR stimulates cell proliferation, transformation and ant...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F1/12C07F9/6561A61K31/555A61K31/675A61P35/00
CPCC07F1/00C07F9/6561
Inventor 李敏勇史晓东杜吕佩
Owner SHANDONG UNIV
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