8-substituted 1,6-diazabenzanthrone derivatives and their synthesis methods and applications

A synthesis method and technology of benzanthrone, applied in the field of 8-substituted 1,6-diazabenzanthrone derivatives and their synthesis, to achieve good medicinal value and high blood-brain barrier permeability

Active Publication Date: 2021-06-22
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no report on the inhibitory activity of acetylcholinesterase after the substituent is attached to the 8-position of the sampangine alkaloid core

Method used

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  • 8-substituted 1,6-diazabenzanthrone derivatives and their synthesis methods and applications
  • 8-substituted 1,6-diazabenzanthrone derivatives and their synthesis methods and applications
  • 8-substituted 1,6-diazabenzanthrone derivatives and their synthesis methods and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Example 1: Synthesis of 4-methyl-1-aza-5,10-anthraquinone (compound 3)

[0047] Under electromagnetic stirring, compound 1 (40.0g, 169.5mmol), xylene (500mL), and compound 2 (28.2g, 2.5mol) were successively added to a 1L round-bottomed flask, and refluxed for 6h (monitoring the reaction with TLC, developing Agent: V 乙酸乙酯 :V 石油醚 =1:1). After the reaction is completed, cool, transfer the product to an extraction bottle, extract with ethyl acetate (6×200ml), combine the organic phases, extract with 2N sulfuric acid (4×500ml), and obtain the acid layer solution Neutralize with 6N sodium hydroxide solution in an ice bath, adjust pH=9, filter with suction, and dry to obtain a crude product, which is purified by silica gel column chromatography (petroleum ether / ethyl acetate=100:1) to obtain compound 3 as gray Solid, yield 60%.

[0048] 1 H NMR (500MHz, Chloroform-d) δ: 8.88(d, J=4.8Hz, 1H), 8.37–8.31(m, 1H), 8.26~8.20(m, 1H), 7.85~7.76(m, 2H), 7.48(dd,J=4.8,0.9Hz,1H),2....

Embodiment 2

[0051] Example 2: Synthesis of 4-methyl-9-nitro-1-aza-5,10-anthraquinone (compound 4)

[0052] Under electromagnetic stirring, compound 3 (6.0 g, 26.9 mol) was added into a 100 mL round-bottomed flask, and concentrated sulfuric acid (25 mL) was slowly added dropwise under ice-bath conditions. After compound 3 was completely dissolved, fuming nitric acid ( 10mL); Reaction 24h (monitoring reaction with TLC, developer: V 乙酸乙酯 :V 石油醚 =2:1). After the reaction was completed, the mixture was slowly added to a beaker equipped with a small amount of ice water, neutralized by adding 6N sodium hydroxide solution dropwise in an ice bath, adjusted to pH=10, cooled, suction filtered, and dried. The crude product of compound 4 was obtained (the product can be directly subjected to the next step of reduction without purification).

Embodiment 3

[0053] Example 3: Synthesis of 4-methyl-9-amino-1-aza-5,10-anthraquinone (compound 5)

[0054] Under electromagnetic stirring, sequentially add the crude product of compound 4 (5.0 g), sodium sulfide nonahydrate (30.0 g), and absolute ethanol (250 mL) into a 500 mL round bottom flask, and reflux for 5 h (monitor the reaction with TLC, developing solvent: V 乙酸乙酯 :V 石油醚 =2:1). After the reaction was completed, cool, filter, and dry to obtain a crude product, which was purified by silica gel column chromatography (dichloromethane as the eluent) to obtain compound 5 as a red solid with a yield of about 70%.

[0055] 1 H NMR (400MHz, DMSO-d 6 )δ: 8.82(d, J=4.7Hz, 1H), 8.01(s, 2H), 7.60(d, J=4.6Hz, 1H), 7.50(t, J=7.8Hz, 1H), 7.30(d, J=7.2Hz, 1H), 7.17(d, J=8.4Hz, 1H), 2.75(s, 3H). 13 C NMR (100MHz, DMSO-d 6 )δ: 184.9, 182.29, 153.09, 151.9, 150.6, 149.9, 134.8, 134.3, 130.4, 128.1, 123.0, 115.3, 111.8, 22.1. HRMS (ESI) m / z: calcd for C 14 h 11 N 2 o 2 [M+H] + :239.0815, f...

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Abstract

The invention discloses a class of 8-substituted 1,6-diazabenzanthrone derivatives, a synthesis method and application thereof. The derivative has a structure shown in the following formula (I), and its synthesis method is: the compound shown in the formula (II) is nitrated, and the compound shown in the formula (III) obtained reacts with sodium sulfide in the first organic solvent to obtain The compound shown in formula (Ⅳ); react it with DMF-DMA in the second organic solvent, add ammonium chloride and weak acid reaction after the reaction is completed, and the whole reaction is carried out under the protection of atmosphere, and the compound shown in gained formula (Ⅴ) Then react with the acid chloride shown in formula (VI) in the third organic solvent to obtain the corresponding crude product of the target compound; the compounds of the structure shown in the formula (I) to formula (VI) are respectively as follows: wherein, n =1~3;R 2 for‑N(CH 3 ) 2 ,-NEt 2 ,

Description

technical field [0001] The invention relates to 1,6-diazabenzanthrone derivatives, in particular to 8-substituted 1,6-diazabenzanthrone derivatives and a synthesis method and application thereof. Background technique [0002] Alzheimer's disease (AD), commonly referred to as senile dementia, was discovered at the beginning of the last century and is a degenerative disease of the central nervous system. The onset of the disease is insidious, and the clinical manifestations are the gradual decline of cognitive and memory functions and self-care ability of daily life, and with the development of the disease, it will be accompanied by various mental symptoms and behavioral disturbances. The disease is mainly concentrated in people over 65 years old, and the incidence rate increases with age. Since AD ​​disease involves a variety of pathological processes, its pathogenesis is a very complex, multi-mechanism, and multi-factor process. [0003] The main pathological features of t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/06A61K31/4745A61K31/496A61P25/28A61P27/06A61P21/04
CPCA61P21/04A61P25/28A61P27/06C07D471/06
Inventor 唐煌李卫何艳红
Owner GUANGXI NORMAL UNIV
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