Naphthylamine derivative and purpose thereof

A technology of naphthalimide and derivatives, which is applied in the field of naphthalimide derivatives, can solve the problems of not being able to be used for treatment and high clinical toxicity, and achieve the effect of good inhibitory activity and simple synthesis method

Inactive Publication Date: 2013-02-06
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Tropak et al. used high-throughput screening methods to obtain several new inhibitor structures that are not based on sugar groups. Among them, a bis-naphthoimide has the best inhibitory effect, but due to its high clinical toxicity, it cannot be used for treatment. Research

Method used

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  • Naphthylamine derivative and purpose thereof
  • Naphthylamine derivative and purpose thereof
  • Naphthylamine derivative and purpose thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Synthesis of 2-(2-aminoethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione (Al)

[0042]

[0043] In a 25mL round bottom flask, add 1,8-naphthalene anhydride (2g, 10.1mmol), 50mL of absolute ethanol and ethylenediamine (1.35mL, 20.2mmol) successively, and the mixture is heated to reflux for 2 hours. After the reaction is completed, depressurize The solvent and excess ethylenediamine were evaporated, and the crude product was recrystallized from absolute ethanol to obtain product A1 (1.8 g) as a light yellow solid with a yield of 74%.

[0044] Melting point: 141-142°C.

[0045] 1 H NMR (400MHz, DMSO-d 6 ): δ=8.34(d, J=7.6Hz, 2H), 8.31(d, J=8.0Hz, 2H), 7.75(dd, J=8.0, 7.6Hz, 2H), 4.01(t, J=6.8Hz , 2H), 2.79(t, J=6.8Hz, 2H), 2.62ppm(br, 2H); 13 CNMR (100MHz, DMSO-d 6 ): δ=163.9, 134.4, 131.5, 130.9, 127.7, 127.4, 122.4, 43.2, 40.2ppm; HRMS-ESI (m / z): calculated value: C 14 h 13 N 2 o 2 [M+H] + , 241.0977; experimental value, 241.0978.

Embodiment 2

[0047] Synthesis of 2-(2-((2-hydroxyethyl)amino)ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione (A2)

[0048]

[0049] In a 25mL round bottom flask, add 1,8-naphthalene anhydride (198mg, 1.00mmol) successively, 10mL absolute ethanol and hydroxyethylethylenediamine (140mg, 1.00mmol), the mixture was heated to reflux for 2 hours, after the reaction was complete, The solvent was evaporated under reduced pressure, and the crude product was recrystallized from absolute ethanol to obtain the product A2 (241 mg) as a white solid with a yield of 85%.

[0050] 1 H NMR (CDCl 3 , 400MHz): δ=8.55(d, J=7.2Hz, 2H), 8.17(d, J=8.0Hz, 2H), 7.71(dd, J=8.0, 7.2Hz, 2H), 4.32(t, J= 6.0Hz, 2H), 3.61(t, J=4.4Hz, 2H), 3.02(t, J=6.0Hz, 2H), 2.84(t, J=4.4Hz, 2H), 2.2ppm(br, 2H); 13 C NMR (100MHz, CDCl 3 ): δ=164.5, 134.0, 131.5, 131.3, 128.1, 126.9, 122.5, 61.0, 50.9, 47.4, 40.1 ppm. EI MS (m / e): 285.4 (M+1, 100).

Embodiment 3

[0052] Synthesis of 2-(2-((2-aminoethyl)amino)ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione (A3)

[0053]

[0054] Add 1,8-naphthalene anhydride (198mg, 1.0mmol), 20mL absolute ethanol and 2mL diethylenetriamine (excessive amount) successively in a 50mL round bottom flask, and heat the mixture to reflux for 2 hours. After the reaction is complete, filter and collect the filtrate , evaporated the solvent under reduced pressure, washed with water, extracted three times with dichloromethane, collected the organic layer, evaporated the solvent under reduced pressure to obtain a white solid, and the crude product was recrystallized with absolute ethanol to obtain the white solid product A3 (189mg), the yield 67 %.

[0055] 1 H NMR (CDCl 3 , 400MHz): δ=8.54(d, J=6.8Hz, 2H), 8.17(d, J=8.0Hz, 4H), 7.71(t, J=7.6Hz, 2H), 4.32(t, J=6.0Hz , 2H), 3.01(t, J=6.4Hz, 2H), 2.77ppm(s, 4H); 13 C NMR (100MHz, CDCl 3 ): δ=164.0, 133.6, 131.2, 130.9, 127.8, 126.6, 122.2, 51.8, 47.2, 41.4, 39...

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Abstract

The inventor of the invention utilizes the medicinal chemical principle to design and synthetize a series of novel naphthylamine derivatives, and performs an inhibitory activity test of the kind of derivative on human N-acetyl amino glycosidase. The test result shows that the inhibitory activity effect is good, and the inhibition effect of some compounds is obviously higher than that of reference compounds reported in literatures. According to the invention, the naphthylamine derivative is free of a glycosyl structure; and the synthesis method is relatively simpler. Therefore, the naphthylamine derivative lays foundation for the development of new medicines used for curing illness relative to human Beta-N-acetyl amino glycosidase.

Description

technical field [0001] The present invention relates to a naphthalimide derivative and its use (as an inhibitor of human β-N-acetylhexosaminidase). Background technique [0002] Carbohydrates play an important role in organisms, not only occupying a central position in the energy metabolism process, but also participating in various physiological and pathological processes including maintaining the integrity of organism structure, cell recognition, signal transduction, inflammatory response, and the proliferation of cancer cells. Since the physiological process involved in carbohydrates is so complex, there are many kinds of enzymes involved in carbohydrate metabolism. So far, the enzymes involved in carbohydrate hydrolysis that have been discovered belong to 114 families. [0003] β-N-acetyl-D-hexosaminidase (EC3.2.1.52) in human and mammalian lysosomes is involved in the hydrolysis of glycosylated moieties in various carbohydrate complexes. There are three kinds of β-N-a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/14C07D405/12C07D401/12A61K31/473A61P43/00
Inventor 郭朋刘田陈琦徐林杨青钱旭红
Owner EAST CHINA UNIV OF SCI & TECH
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