Borate compound for cancer boron neutron capture therapeutic drug and preparation thereof

A boron neutron capture, boric acid compound technology, applied in the field of medicinal chemistry and radiation medicine, can solve the problems of limited research, high instability, etc., to achieve the effect of expanding the scope, strong selectivity, and good efficiency

Active Publication Date: 2022-04-29
LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Four-coordinate boric acid compounds have a certain weak basicity, which is a common intermediate in the chemical reaction of organoboric acid molecules. Due to their high instability, the research on this type of compounds is extremely limited.

Method used

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  • Borate compound for cancer boron neutron capture therapeutic drug and preparation thereof
  • Borate compound for cancer boron neutron capture therapeutic drug and preparation thereof
  • Borate compound for cancer boron neutron capture therapeutic drug and preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Example 1: Preparation of borate compound (1) (two-step method).

[0057]

[0058] Under air atmosphere, (L)-4-dihydroxyboryl phenylalanine (0.05 mmol, 10.45 mg), sodium hydroxide (0.15 mmol, 6 mg ), toluene (4 mL) and a magnetic stir bar were added to 35 mL glass pressure-resistant tube. Then triphenylsilane (0.15 mmol, 39 mg) was added, and the reaction tube was reacted at 90°C for 6 hours. After the reaction is completed, the reaction system is cooled to room temperature, the reaction vessel is opened at room temperature, and is filtered; the obtained solid is recrystallized and separated to obtain the reaction product. The pure product yield of target product is 78%.

[0059] 1 H NMR (300 MHz, DMSO) δ 12.89 (s, 1H), 8.71 (d, 2H), 7.75 (d, 2H), 7.46 (m, 18H), 7.39-7.35 (m, 27H), 7.2(d, 2H), 4.18(s, 1H), 3.42(d, 2H).

[0060] 13 C NMR (100 MHz, DMSO) δ 174.7, 138.3, 136.6, 135.7, 133.3, 132.5, 130.0, 129.5, 127.7, 56.7, 37.3.

Embodiment 2

[0061] Embodiment 2: the preparation (one-step method) of borate compound (2)

[0062]

[0063] Under air atmosphere, phenylboronic acid (0.05 mmol, 6.1 mg), sodium triphenylsilanolate (0.025 mmol, 7.46 mg ), and a magnetic stir bar were added to a 35 mL glass pressure-resistant tube. Then toluene (4 mL) was added, and the reaction tube was reacted at 90°C for 6 hours. After the reaction is completed, the reaction system is cooled to room temperature, the reaction vessel is opened at room temperature, and is filtered; the obtained solid is recrystallized and separated to obtain the reaction product. The pure product yield of target product is 75%.

[0064] 1 H NMR (300 MHz, DMSO) δ 7.75(d, 2H), 7.48 - 7.44 (m, 6H), 7.37-7.39(m, 10m) 7.36(s, 1H), 7.35(s, 1H), 4.2 (d , 2H).

[0065] 13 C NMR (101 MHz, DMSO) δ 138.5, 138.3, 133.4, 132.5, 130.0, 129.5, 128.7.

Embodiment 3

[0066] Embodiment 3: the preparation of borate compound (3) (two-step method)

[0067]

[0068] Under air atmosphere, phenylboronic acid (0.05 mmol, 6.1 mg), sodium hydroxide (0.5 mmol, 20 mg), toluene (4 mL) and a magnetic stir bar were added to a 35 mL glass pressure-resistant tube. Then triphenylsilane (0.15 mmol, 39 mg) was added, and the reaction tube was reacted at 90°C for 12 hours. After the reaction is completed, the reaction system is cooled to room temperature, the reaction vessel is opened at room temperature, and is filtered; the obtained solid is recrystallized and separated to obtain the reaction product. The pure product yield of target product is 75%.

[0069] 1 H NMR (300 MHz, DMSO) δ 7.75 (d, 2H), 7.48- 7.44 (m, 18H), 7.34 -7.38 (m, 30H).

[0070] 13 C NMR (101 MHz, DMSO) δ 138.3, 133.4, 132.5, 130.0, 129.5, 128.7.

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Abstract

The present invention relates to a borate compound used for boron neutron capture therapeutic drug for cancer. The general structural formula of the borate compound is as follows: wherein R 1 is aryl, R 2 , R 3 , R 4 All are one of H, alkyl, aryl, silicon, boron. The invention also discloses a preparation method of the borate compound. The invention has good stability and acid resistance, and has strong selectivity to head and neck cancer cells (CAL27).

Description

technical field [0001] The invention relates to the fields of medicinal chemistry and radiation medicine, in particular to a borate compound used for cancer boron neutron capture therapeutic drug and its preparation. Background technique [0002] Head and neck cancer is a cancer with a high incidence rate, which is difficult to treat and has a high mortality rate. Its eradication is a huge challenge in human medicine. In recent years, with the continuous advancement of drug research and development at home and abroad, great progress has been made in the development of anticancer drugs, but new and more effective cancer treatment methods are still urgently needed. [0003] Boron neutron capture therapy (BNCT) is a novel radiotherapy technique targeting tumor cells, BNCT is a binary method based on nuclear capture and fission reactions, which has significantly lower side effects compared with traditional radiotherapy and chemotherapy , high selectivity and high efficiency. N...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/10C07H23/00C07H1/00A61P35/00
CPCC07F7/0834C07H23/00C07H1/00A61P35/00
Inventor 李跃辉
Owner LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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