Benzamide-containing benzo six-membered heterocyclic derivative and application thereof in antitumor drugs

A benzo six-membered, benzamide technology, applied in solvates or prodrugs, anti-tumor drugs, benzo six-membered heterocyclic derivatives, can solve toxic and side effects, and lack of therapeutic targets for anti-tumor drugs etc. to achieve strong anti-tumor activity and ideal inhibition rate

Inactive Publication Date: 2020-12-01
陈爱平
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Tumor treatment is a worldwide problem. Traditional cytotoxic anti-tumor drugs lack definite therapeutic targets and are prone to serious side effects. With the advancement of science and medicine, traditional cytotoxic drugs have shifted from traditional cytotoxic drugs to highly effective drugs with clear targets. Development of new anti-tumor drugs with low toxicity

Method used

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  • Benzamide-containing benzo six-membered heterocyclic derivative and application thereof in antitumor drugs
  • Benzamide-containing benzo six-membered heterocyclic derivative and application thereof in antitumor drugs
  • Benzamide-containing benzo six-membered heterocyclic derivative and application thereof in antitumor drugs

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036]

[0037] Synthesis of Step 1 Intermediate 3

[0038]Benzomorpholine (1.00 g, 7.40 mmol) and methyl 4-bromomethylbenzoate (1.69 g, 7.40 mmol) were dissolved in 30 mL of DMF, then anhydrous potassium carbonate (2.04 g, 14.8 mmol) was added, The temperature was raised to 80°C for reaction. After 6 hours of reaction, TLC detected that the reaction was complete. The reaction solution was cooled to room temperature, and the reaction solution was poured into 150 mL of water. A large amount of solid was precipitated, and 1.88 g of an off-white solid was obtained by filtration, with a yield of 89.7%.

[0039] Synthesis of Step 2 Intermediate 4

[0040] Dissolve intermediate 4 (1.88g, 6.64mmol) in 20mL of ethanol, add 10mL of 2N sodium hydroxide solution, stir at room temperature for 2h, TLC detects that the reaction is complete, distill off ethanol under reduced pressure, add water and adjust with 3N hydrochloric acid When the pH reached 4-5, a large amount of solids were pr...

Embodiment 2

[0046]

[0047] 1 H-NMR (400MHz, DMSO-d 6 )δ9.72(s,1H),7.99(d,J=7.9Hz,2H),7.33(d,J=7.8Hz,2H),7.19(d,J=7.6Hz,1H),7.12-7.10( m,1H),6.95-6.93(m,2H),6.79(d,J=8.1Hz,1H),6.65-6.61(m,3H),5.34(s,2H),4.92(s,2H),3.38 (t, J=7.2Hz, 2H), 2.78(t, J=7.1Hz, 2H), 1.96~1.91(m, 2H).

Embodiment 3

[0049]

[0050] 1 H-NMR (400MHz, DMSO-d 6 )δ9.70(s,1H),8.02(d,J=7.7Hz,2H),7.33(d,J=7.7Hz,2H),7.19(d,J=7.7Hz,1H),6.97-6.95( m,1H),6.84-6.79(m,2H),6.76(d,J=7.8Hz,1H),6.62(t,J=7.6Hz,1H),6.54(d,J=7.8Hz,1H), 5.36(s,2H),4.92(s,2H),4.15(t,J=7.2Hz,2H),3.78(t,J=7.1Hz,2H).

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Abstract

The invention belongs to the technical field of medicines, and particularly relates to a benzamide-containing benzo six-membered heterocyclic derivative and application thereof in antitumor drugs. CCK-8 results show that the benzamide-containing benzo six-membered heterocyclic derivative synthesized in the laboratory has the advantage of high antitumor activity, and can be used for preparing antitumor drugs. An enzyme activity experiment shows that an HDAC inhibitor synthesized by the invention has a relatively ideal HDAC inhibition rate and has a prospect of clinically developing anti-myeloma, anti-gastric cancer, anti-cervical cancer and anti-rectal cancer drugs.

Description

technical field [0001] The present invention belongs to the technical field of medicines, and in particular relates to a benzamide-containing benzo six-membered heterocyclic derivative, geometric isomers thereof or pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof, and Its application in antineoplastic drugs. Background technique: [0002] Tumor has become one of the most important diseases that endanger human health around the world. It is a general term for more than 100 malignant diseases. It is the disease with the highest mortality rate in the world. It is becoming an important burden on the country and social economy and seriously threatens human life and health. . The mortality and prevalence of cancer are increasing year by year, and it has become the leading cause of death and an important public health problem. Tumor treatment is a worldwide problem. Traditional cytotoxic anti-tumor drugs lack definite therapeutic targets and are prone to ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D265/36C07D215/06C07D241/40A61P35/00
CPCA61P35/00C07D215/06C07D241/40C07D265/36
Inventor 陈爱平
Owner 陈爱平
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