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Nitrile substituted phenyl compound and application thereof

A compound, aminoacyl technology, applied in the field of nitrile-substituted phenyl compounds, can solve the problems of side effects, peripheral neurotoxicity, toxicity, etc., and achieve the effect of high safety and good tumor inhibitory activity

Pending Publication Date: 2022-05-31
JIANGSU CANCER HOSPITAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these known radiosensitizers have unresolved issues, such as gastrointestinal dysfunction, peripheral neurotoxicity, and other side effect issues, and are rarely used in practice
[0004] Existing chemotherapeutic agents usually cause significant toxic side effects. Therefore, it is necessary to develop new radiosensitizers that can increase the efficacy of cancer radiotherapy, achieve therapeutic effects with lower radiation doses, and have clinically acceptable toxicity.

Method used

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  • Nitrile substituted phenyl compound and application thereof
  • Nitrile substituted phenyl compound and application thereof
  • Nitrile substituted phenyl compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] The preparation of embodiment 1 compound 1

[0046]

[0047] Step 1 Preparation of compound 1a

[0048]

[0049] In a 500mL single-necked bottle, add 1,4-dioxane (200mL), then sequentially add 3-cyclohexene-1-amine hydrochloride (11g), triphosgene (8.86g) and triethylamine ( 4.02g), reacted at 130°C for 2h. TLC showed that the reaction was complete, and the solvent was removed by rotary evaporation to obtain a crude product, which was separated and purified by column chromatography to obtain the title compound. ESI-MS m / z:[M+H] + =124.3.

[0050] Step 2 Preparation of compound 1b

[0051]

[0052] Dissolve 3-chloropyrrolidine (4g) in 25mL N,N-dimethylformamide, add sodium hydride (2g) under stirring at -5°C, continue stirring for 0.5h, then add compound 1a (9g), and raise room temperature After stirring for 1 h, the reaction was monitored by LC-MS, and the reaction solution was directly injected into the next step. ESI-MS m / z:[M+H] + =229.1.

[0053] St...

Embodiment 2

[0062] The preparation of embodiment 2 compound 2

[0063]

[0064] The preparation method was the same as that in Example 1, except that 4-aminophthalonitrile was replaced by p-aminobenzonitrile to obtain the title compound. ESI-MS m / z:[M+H] + = 311.1.

Embodiment 3

[0065] The preparation of embodiment 3 compound 3

[0066]

[0067] The preparation method was the same as that in Example 1, except that 4-aminophthalonitrile was replaced by m-aminobenzonitrile to obtain the title compound. ESI-MS m / z:[M+H] + = 311.1.

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Abstract

The invention relates to a nitrile substituted phenyl compound and application thereof, in particular to a compound as shown in a formula (I), or pharmaceutically acceptable salt or stereoisomer thereof. The nitrile-substituted phenyl compound disclosed by the invention is combined with radioactive rays, and has good tumor inhibition activity and high safety.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to nitrile-substituted phenyl compounds and applications thereof. Background technique [0002] Radiation therapy is a method of local treatment of malignant tumors that involves the application of ionizing radiation as part of the treatment to control or kill malignant cells. Ionizing radiation damages the DNA of exposed tissues and leads to cell death, allowing normal organs and tissues to survive. Retention, so the number of patients treated by this method is growing rapidly, and it is estimated that about two-thirds of cancer patients receive radiation therapy. Radiation therapy can treat many types of cancer and can also be used as part of adjuvant therapy to prevent tumor recurrence after surgery. Cancers respond differently to radiation by type or size and state: highly radiosensitive cancer cells such as leukemias, most lymphomas, and germ cell tumors are rapi...

Claims

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Application Information

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IPC IPC(8): C07D207/09A61K41/00A61P35/00A61P35/02
CPCC07D207/09A61K41/0038A61P35/00A61P35/02
Inventor 吴俚蓉周佳伟宋雪李阳燕丹何侠
Owner JIANGSU CANCER HOSPITAL
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