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1, 3, 4-oxadiazole derivative as well as preparation method and application thereof

A technology of oxadiazoles and derivatives, applied in different preparation fields, can solve problems such as low solubility, adverse side reactions, low solubility limitation and the like

Active Publication Date: 2021-09-07
JIANGSU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

AZ20 is a developed ATR inhibitor with low nanomolar activity, and its inhibitory activity on ATR is IC 50 =5nM, can significantly reduce the tumor volume of mice transplanted with LoVo colorectal cells, but the low solubility of the inhibitor limits further research
Therefore, in view of the insufficient quantity of ATR inhibitors at this stage, low solubility and adverse side effects in clinical trials, it is still of great practical significance to develop new specific ATR inhibitors.

Method used

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  • 1, 3, 4-oxadiazole derivative as well as preparation method and application thereof
  • 1, 3, 4-oxadiazole derivative as well as preparation method and application thereof
  • 1, 3, 4-oxadiazole derivative as well as preparation method and application thereof

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Embodiment Construction

[0023] The present invention will be further described through specific embodiments below in conjunction with the accompanying drawings. These embodiments are only used to illustrate the present invention, and are not intended to limit the protection scope of the present invention.

[0024] The specific implementation method of compound I preparation is as follows:

[0025] Step a: Dissolve methyl 3-amino-6-bromopyrazine-2-carboxylate (5.0 g, 21.55 mmol) in an aqueous solution of hydrochloric acid (5.47 mL, 53.88 mmol) (the volume ratio of hydrochloric acid to water is 1:1) Stir until it becomes a paste, and react at room temperature for 20 minutes. After cooling the reaction system to 0 °C, 20 mL NaNO was added dropwise 2 (1.64g, 23.7mmol) aqueous solution, after fully stirring and reacting at 0°C for 10min, add dropwise HBF with a volume ratio of 40% 4Aqueous solution (14.2 mL, 66.45 mmol), after the dropwise addition was completed, the reaction was continued at room tempe...

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Abstract

The invention discloses a 1, 3, 4-oxadiazole derivative, and discloses different preparation methods of the 1, 3, 4-oxadiazole derivative and an application thereof. The compound can be used for preparing inhibitors and anti-tumor drugs of ataxia telangiectasia mutant genes and Rad3 related kinase (ATR). The 1, 3, 4-oxadiazole derivative disclosed by the invention is novel in structure, and an electron withdrawing group (nitryl) of a side-chain benzene ring is beneficial to improving the anti-tumor activity of the 1, 3, 4-oxadiazole derivative. Compared with a traditional preparation method of the 1, 3, 4-oxadiazole derivative, the preparation method of the 1, 3, 4-oxadiazole derivative can overcome the defects that under the high-temperature reaction condition, a dehydration cyclizing agent is high in toxicity, prone to corrosion and the like, dibromotriphenylphosphine is adopted as a dehydration cyclizing agent in the preparation method, reaction can be conducted at the room temperature, and the preparation method is environmentally friendly.

Description

technical field [0001] The invention discloses a 1,3,4-oxadiazole derivative, and discloses different preparation methods and new applications of the 1,3,4-oxadiazole derivative. It can be used to prepare inhibitors of ataxia telangiectasia mutation gene and Rad3-related kinase (ATR) and anti-tumor drugs. Background technique [0002] Ataxia telangiectasia and Rad-3 related protein kinase (ATR), as an important protein kinase in the PIKK family, are not only related to gene recombination, but also play a key regulatory role in the DNA damage repair pathway. After receiving upstream regulatory signals, ATR can phosphorylate a series of downstream proteins, control cell cycle division, and promote deoxyribonucleotide synthesis, thereby ensuring the integrity of the genome. Impaired physiological function of ATR can lead to a series of diseases, including immunodeficiency, nervous system disorders and cancer. Due to the defects in the DNA damage response mechanism in tumor ce...

Claims

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Application Information

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IPC IPC(8): C07D413/14A61P35/00
CPCC07D413/14A61P35/00
Inventor 芮蒙杰王立龙冯春来季薇
Owner JIANGSU UNIV
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