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A class of dipeptide boronic acid compound and its preparation method and use

A dipeptide boronic acid and compound technology, applied in the field of dipeptide boronic acid compounds, can solve problems such as toxic and side effects, and achieve high activity, significant effect, and the effect of inhibiting proteasome

Active Publication Date: 2018-08-17
成都四面体药物研究有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the currently marketed anticancer drugs have serious side effects

Method used

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  • A class of dipeptide boronic acid compound and its preparation method and use
  • A class of dipeptide boronic acid compound and its preparation method and use
  • A class of dipeptide boronic acid compound and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Methyl 3-aminobenzoate (1.35g, 7.35mmol), pyridine-3-carboxylic acid (1.0g, 7.35mmol) and TBTU (2.86g, 22.35mmol) were put into a 50mL round bottom flask, and DMF (18mL) was added to dissolve Clear, cool down to 0°C in an ice-water bath, add DIPEA (2.88g, 8.94mL) dropwise, after the addition is complete, stir at room temperature overnight, dilute with ethyl acetate (20mL), and successively add 1mol / L hydrochloric acid (10mL) and saturated sodium bicarbonate The solution (10 mL) was washed, dried over anhydrous sodium sulfate, filtered, and concentrated to obtain 1.3 g of brown oil.

[0049] Put the brown oil and sodium hydroxide (1g, 25mmol) into a 50mL original bottom flask, add methanol (25mL) to dissolve, stir at room temperature overnight, spin to dry the solvent, and dissolve the residue in water (20mL) for clarification. Adjust the pH to 5 with hydrochloric acid, and filter with suction to obtain 1.1 g of a white intermediate solid, with a yield of 91.2%.

[0050] ...

Embodiment 2

[0057] The difference between this example and Example 1 is that the pyridine-3-carboxylic acid in Example 1 was replaced with benzoic acid, the obtained brown oil was 1.5g, and then the obtained white intermediate solid was 1.1g. The rate is 91.2%.

[0058] The structure of the white intermediate solid is:

[0059] The yellow intermediate solid was 0.39 g, and the yield was 65%. The structure of the yellow intermediate solid is:

[0060] The finished product of white solid is 80 mg, and the yield is 33%. The white solid finished product is the finished product 2.

[0061] The structure of finished product 2 is: The spectrum detection results of this structure are as follows:

[0062] MS m / z 337 (M-OH); 1 H-NMR (400MHz, DMSO) δ(ppm): 10.47~10.51(d, 1H), 7.96~8.06(m, 2H), 7.70~7.78(m, 1H), 7.78~7.61(m, 3H), 1.76 ~1.79(t, 1H), 1.40~1.45(m, 2H), 1.17~1.23(m, 1H), 0.57~0.83(t, 6H).

Embodiment 3

[0064] The difference between this example and Example 1 is that the pyridine-3-carboxylic acid (1.0g, 7.35mmol) in Example 1 was replaced by 2-furancarboxylic acid (0.98g, 8.8mmol), and the brown oil obtained was 1.5g, put the brown oil and sodium hydroxide (1g, 25mmol) into a 50mL original bottom flask, add methanol (25mL) to dissolve, stir at room temperature overnight, spin to dry the solvent, and dissolve the residue with water (20mL). Adjust the pH to 5 with 2 mol / L hydrochloric acid, and filter with suction to obtain 0.98 g of white intermediate solid, with a yield of 83.2%.

[0065] The structure of the white intermediate solid is:

[0066] Put the above-mentioned white intermediate solid (0.34g, 1.45mmol), raw material three (0.5g, 1.32mmol) and TBTU (0.51g, 1.58mmol) into a 50mL round-bottomed flask, add DMF (4mL) to dissolve, and cool to At 0°C, DIPEA (2.88g, 8.94mL) was added dropwise. After the addition was complete, the mixture was stirred at 0°C for 5min, the...

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Abstract

The invention discloses a class I dipeptidyl boric acid compound and a preparation method and an application thereof, and aims to provide a novel boric acid compound with a novel structure and a function of restraining proteasome. The class I dipeptidyl boric acid compound is shown as a formula I shown in the description, wherein R is shown in the description. The class I dipeptidyl boric acid compound has the effects of blocking tumor cell proliferation and inducing cancer cell apoptosis, so that the compound can be used for treating a plurality of diseases such as malignant tumors.

Description

technical field [0001] The present invention relates to peptide-containing boronic acid compounds, in particular to dipeptide boronic acid compounds, and to the synthesis methods of these compounds. Background technique [0002] Malignant tumor is still a major disease that threatens people's life and health. Although humans have made gratifying progress in the treatment of malignant tumors, there is still a long way to go before curing cancer. Most of the currently marketed anticancer drugs have serious side effects. How to study new targeted anticancer drugs by inhibiting related tumor-inducing enzymes has become an important way for pharmaceutical scientists to study new drugs. [0003] The production and degradation of intracellular proteins must maintain a dynamic balance in order to maintain the homeostasis and normal function of cells. The ubiquitin-proteasome pathway can efficiently and selectively degrade intracellular proteins, especially some short-lived cell c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02A61P35/00
CPCC07F5/025
Inventor 陈少武唐克慧曹胜华邱东辉潘美英林世博覃传军
Owner 成都四面体药物研究有限公司
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