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Application of 5-hydrogen-1,4-benzodiazepine compound in treatment of liver cancer

A benzodiazepine, a technology for the treatment of liver cancer, applied in medical preparations containing active ingredients, organic chemistry, drug combinations, etc., can solve problems such as less research, achieve strong inhibitory activity, and good development and application prospects Effect

Active Publication Date: 2017-06-30
SHANGHAI JIAO TONG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] As an important class of 1,4-benzodiazepines, less research has been done on 5-hydrogen-1,4-benzodiazepines; among them, 5-hydrogen-1,4- The biological activity of benzodiazepines has not been reported

Method used

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  • Application of 5-hydrogen-1,4-benzodiazepine compound in treatment of liver cancer
  • Application of 5-hydrogen-1,4-benzodiazepine compound in treatment of liver cancer
  • Application of 5-hydrogen-1,4-benzodiazepine compound in treatment of liver cancer

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preparation example Construction

[0031] A kind of 5-hydrogen-1 of the present invention, the synthetic route of 4-benzodiazepine compound is as follows figure 2 Shown; Its concrete synthetic method comprises the following steps:

[0032] (1) In the reaction device, sequentially add 1 to 50 mol% iodine elemental catalyst, 1,2-disubstituted acetylene compound and organic solvent, and react under heating at 50 to 140°C;

[0033] (2) After reacting for a period of time, add 2-aminobenzylamine compound and acidic compound successively, continue heating reaction;

[0034] (3) After the reaction is complete, the 5-hydrogen-1,4-benzodiazepines are obtained through conventional post-treatment.

[0035] In step (1), the reaction temperature can be selected to be 80-140°C, and generally 130°C is more selected during the reaction process; in step (2), the reaction temperature can be selected to be 80-120°C, generally during the reaction The process would be more preferably 100°C.

Embodiment 1

[0039] The synthesis of 2,3-diphenyl-5-hydrogen-1,4-benzodiazepine (compound 1), its structural formula is:

[0040]

[0041] Into the reaction tube, add 10.1 mg of iodine, 35.6 mg of 1,2-toluene, and 2 mL of dimethyl sulfoxide in sequence, react in an oil bath at 130°C for 24 hours, cool the reaction solution to room temperature, and then add 97.7 mg of 2-aminobenzylamine and 1 mL of acetic acid were reacted in an oil bath at 100°C for 20 hours, and finally 51.6 mg of compound 1 was obtained by conventional post-treatment, with a yield of 87%.

[0042] Compound 1 has a melting point of 131-132°C.

[0043] The NMR characterization results of compound 1 are: 1 H NMR (400MHz, CDCl 3 ): δ 7.88-7.77(m, 2H), 7.57-7.47(m, 3H), 7.42-7.30(m, 5H), 7.21(t, J=7.0Hz, 4H), 4.86(d, J=10.6Hz , 1H), 3.97(d, J=10.6Hz, 1H); 13 C NMR (100MHz, CDCl 3 )δ 54.8, 125.7, 126.8, 128.0, 128.3, 128.4, 128.5, 128.6, 129.9, 130.7, 130.8, 137.4, 137.8, 147.5, 160.5, 160.6.

Embodiment 2

[0045] The synthesis of 2,3-bis(4-methylphenyl)-5-hydrogen-1,4-benzodiazepine (compound 2), its structural formula is:

[0046]

[0047] Into the reaction tube, add 10.1 mg of iodine, 41.2 mg of 1,2-di(4-methylphenyl)acetylene, and 2 mL of dimethyl sulfoxide in sequence, react in an oil bath at 130°C for 24 hours, and cool the reaction solution to At room temperature, 97.7mg of 2-aminobenzylamine and 1mL of acetic acid were added in sequence, and placed in an oil bath at 100°C for 20 hours. Finally, 48.0mg of compound 2 was obtained by conventional post-treatment, with a yield of 74%.

[0048] Compound 2 has a melting point of 150-152°C.

[0049] The NMR characterization results of compound 2 are: 1 H NMR (400MHz, CDCl 3 ): δ 7.72(d, J=8.0Hz, 2H), 7.51(d, J=7.7Hz, 1H), 7.45-7.30(m, 4H), 7.21-7.09(m, 3H), 7.00(d, J =7.8Hz, 2H), 4.81(d, J=10.6Hz, 1H), 3.95(d, J=10.6Hz, 1H), 2.31(s, 3H), 2.22(s, 3H); 13 C NMR (100MHz, CDCl 3 )δ 21.4, 21.5, 54.7, 125.6, 126.5, 127.9, 128.3, ...

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Abstract

The invention discloses application of a 5-hydrogen-1,4-benzodiazepine compound in treatment of the liver cancer. The 5-hydrogen-1,4-benzodiazepine compound has a good inhibition effect on human hepatocarcinoma cell lines HepG2 and Huh7; in seven tested 5-hydrogen-1,4-benzodiazepine compounds, when the concentration of the compound VII is 30 [mu]M, the rate of inhibiting the human hepatocarcinoma cell line HepG2 can be up to 70 percent, and the rate of inhibiting the human hepatocarcinoma cell line Huh7 can be up to 64 percent. The invention discloses the application of the type of compounds in preparation of a liver cancer treatment medicine; furthermore, the compounds are high in inhibition activity for hepatoma cells, so that the 5-hydrogen-1,4-benzodiazepine compound has a good development and application prospect in preparation of anti-liver cancer medicines.

Description

technical field [0001] The invention relates to the medical use of 5-hydrogen-1,4-benzodiazepine compounds, in particular to the application of 5-hydrogen-1,4-benzodiazepine compounds in treating liver cancer. Background technique [0002] Benzodiazepine structural units exist in a series of natural products and drug molecules with physiological activities. For example, 1,5-benzodiazepine compounds are often used as anxiolytics, antidepressants, anticonvulsants, Drugs for sedation and analgesia; and 1,4-benzodiazepines also show good biological activity, such as drugs commonly used as anti-anxiety and antidepressants. [0003] As an important class of 1,4-benzodiazepines, less research has been done on 5-hydrogen-1,4-benzodiazepines; among them, 5-hydrogen-1,4- The biological activity of benzodiazepines has not been reported yet. Therefore, it is of great significance to study the application of such compounds. Contents of the invention [0004] The present invention pr...

Claims

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Application Information

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IPC IPC(8): A61K31/5513C07D409/04C07D243/14A61P35/00
CPCA61K31/5513C07D243/14C07D409/04
Inventor 郭勋祥訾晶何昆燕张燕
Owner SHANGHAI JIAO TONG UNIV
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