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Class I dipeptidyl boric acid compound and preparation method and application thereof

A technology of dipeptide boronic acid and compound, which is applied in the field of dipeptide boronic acid compound, can solve problems such as toxic and side effects, achieve high activity, block tumor cell proliferation, and have remarkable effects

Active Publication Date: 2016-10-12
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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  • Class I dipeptidyl boric acid compound and preparation method and application thereof
  • Class I dipeptidyl boric acid compound and preparation method and application thereof
  • Class I dipeptidyl boric acid compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0049] Put the brown oil and sodium hydroxide (1g, 25mmol) into a 50mL original bottom flask, add methanol (25mL) to dissolve it, stir overnight at room temperature, spin off the solvent, and dissolve the residue with water (20mL) for clarity, use 2mol / L The pH was adjusted to 5 with hydrochloric acid and filtered with suction to obtain 1.1 g of a white intermediate solid with a yield of 91.2%.

[0050] The structure of the wh...

Embodiment 2

[0057] The difference between this example and Example 1 is that the pyridine-3-carboxylic acid in Example 1 is replaced with benzoic acid, the brown oily substance obtained is 1.5g, and the white intermediate solid obtained is 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 white solid product is 80 mg, and the yield is 33%. The white solid finished product is finished product 2.

[0061] The structure of finished product 2 is: The results of the map detection of the 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 (1.0 g, 7.35 mmol) in Example 1 is replaced with 2-furan carboxylic acid (0.98 g, 8.8 mmol), and the brown oil obtained is 1.5g, put the brown oil and sodium hydroxide (1g, 25mmol) into a 50mL original bottom flask, add methanol (25mL) to dissolve it, stir overnight at room temperature, spin off the solvent, and dissolve the residue with water (20mL) for clarity. The pH of 2mol / L hydrochloric acid was adjusted to 5, and the obtained white intermediate solid was 0.98 g and the yield was 83.2%.

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

[0066] Put the above white intermediate solid (0.34g, 1.45mmol), raw material three (0.5g, 1.32mmol) and TBTU (0.51g, 1.58mmol) into a 50mL round bottom flask, add DMF (4mL) to dissolve, and cool to At 0°C, DIPEA (2.88g, 8.94mL) was added dropwise, after addition, stirred at 0°C for 5min, saturated sodium bicarbonate solution (25mL) was ...

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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 methods for synthesizing these compounds. Background technique [0002] Malignant tumors are still a major disease threatening people's lives and health. Although human beings have made gratifying progress in the treatment of malignant tumors, there is still a long way to go to cure cancer. Most anti-cancer drugs currently on the market have serious side effects. How to study targeted new 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 to maintain cell homeostasis and normal functions. The ubiquitin-proteasome pathway can efficiently and selectively degrade intracellular proteins, especially some short-lived cell cycle regulatory proteins...

Claims

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Application Information

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Patent Type & Authority Applications(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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