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Glycinamide derivative as well as preparation method and application thereof

A technique for glycinamide and derivatives, applied in the field of glycinamide derivatives and their preparation

Active Publication Date: 2021-06-11
GUILIN MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far, there are no literature and patent reports that glycinamide SAHase inhibitors have anti-tumor activity

Method used

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  • Glycinamide derivative as well as preparation method and application thereof
  • Glycinamide derivative as well as preparation method and application thereof
  • Glycinamide derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1: the preparation of compound 22-23

[0032]

[0033] Compound 2,3-dihydro-1H-indan-2-amine hydrochloride (V, 0.012mol), triethylamine (0.035mol), di-tert-butyl dicarbonate (0.013mol) were dissolved in dichloromethane (50mL), stirred at room temperature for 3h, after the reaction was complete, added water (20mL×2) to wash, washed once with saturated brine, anhydrous MgSO 4 Dry, filter, and concentrate to give a white solid intermediate;

[0034] In the reaction flask, first add LiAlH 4 (0.024mol), under nitrogen protection, slowly add anhydrous tetrahydrofuran (25mL) under ice bath, then dissolve the white solid intermediate in anhydrous tetrahydrofuran (35mL), and slowly drop into the reaction flask under ice bath ;

[0035] After dropping, heat to reflux, after the reaction is complete, cool to room temperature, pour the reaction solution into 10% aqueous sodium hydroxide solution (120mL), then extract with dichloromethane (60mL×3), wash once with sa...

Embodiment 2

[0041] Embodiment 2: the preparation of compound 1-5

[0042]

[0043] In a three-necked reaction flask, add 3-(4-chlorophenyl)glutaric acid (4.1mmol) and Ac 2 O (20mL), stirred, heated to 100°C, reacted for 2h, then concentrated to dryness to obtain an oil. Anhydrous tetrahydrofuran (20 mL), triethylamine (10.3 mmol) and 2-aminoindane hydrochloride (4.1 mmol) were added to the above oil, and stirred overnight at room temperature. After the reaction was complete, it was concentrated to dryness, added water (60 mL), extracted with ethyl acetate (30 mL×3), washed once with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated to dryness to obtain an oil. To the above oil, dichloromethane (30 mL), 2-(7-azabenzotriazole)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATU, 4.9 mmol), N,N-diisopropylethylamine (DIPEA, 8.2mmol) and 1-(2-aminoethyl)piperidine (4.9mmol), stirred overnight at room temperature. After the reaction is complete, adjus...

Embodiment 3

[0053] Embodiment 3: the preparation of compound 6-9

[0054]

[0055] In a three-necked reaction flask, add 3-phenylglutaric acid (4.8mmol) and Ac 2 O (20mL), stirred, heated to 100°C, reacted for 2h, concentrated to dryness to obtain an oil. Anhydrous tetrahydrofuran (20 mL), triethylamine (12.0 mmol) and 2-aminoindane hydrochloride (4.8 mmol) were added to the above oil, and stirred overnight at room temperature. After the reaction was complete, the reaction solution was concentrated to dryness, poured into water (60 mL), extracted with ethyl acetate (30 mL×3), washed once with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated to dryness to obtain an oil. To the above oil, dichloromethane (30 mL), 2-(7-azabenzotriazole)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATU, 5.8 mmol), N,N-diisopropylethylamine (DIPEA, 9.6mmol) and 1-(2-aminoethyl)piperidine (5.8mmol), stirred overnight at room temperature. After the reaction is compl...

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Abstract

The invention discloses a glycinamide derivative as well as a preparation method and application thereof. The derivative with a structural formula as shown in the following formula (I) is provided; and in the formula, R1 is selected from Cl and H, R2 is one selected from H, CH3 and CH2CH3; and X is one selected from NHCH3, NHCH2CH3, N (CH2CH3) 2, a pyrrolyl group and a piperidyl group. During preparation, different phenyl glutaric acid compounds are selected as raw materials and are respectively subjected to amidation reaction twice with an aminoindane hydrochloride derivative and an ethylenediamine derivative to obtain a target derivative. The prepared derivative or the pharmaceutically acceptable salt thereof, or the pharmaceutical composition thereof can be used as an S-adenosyl homocysteine hydrolase inhibitor for the development of antitumor drugs .

Description

technical field [0001] The invention belongs to the field of new drug design and synthesis, in particular to a glycinamide derivative and its preparation method and application. Background technique [0002] So far, cancer is still an important factor leading to human death worldwide, seriously endangering people's health. At present, the morbidity and mortality of malignant tumors are increasing worldwide. In my country, the main fatal malignant tumors are lung cancer, gastric cancer, liver cancer, colorectal cancer and breast cancer. Multidrug resistance is one of the main reasons for the failure of chemotherapy and ineffective clinical treatment of malignant tumors. How to overcome the drug resistance of tumor cells is a major problem in the field of tumor treatment. Therefore, it is imminent to develop new anti-tumor drugs for the treatment of malignant tumors. . [0003] S-adenosyl homocysteine ​​hydrolase (SAHase) catalyzes the hydrolysis of S-adenosyl homocysteine ​...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/13C07C233/40C07C269/04C07C271/24C07C209/68C07C211/42C07D309/32C07C231/02C07C233/11C07C231/14A61P35/00
CPCC07D295/13C07C233/40C07C269/04C07C209/68C07D309/32C07C231/02C07C231/14A61P35/00C07C2602/08C07C271/24C07C211/42C07C233/11
Inventor 谭相端吕玉彬马瑞婧陈聪周异欢彭彦芬周香辉程娃
Owner GUILIN MEDICAL UNIVERSITY
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