Preparation method for 4-phenyl-2,7-naphthyridine-1(2H)-ketone

A technology of naphthyridine and phenyl, which is applied in the field of drug synthesis, can solve the problems of many route steps, low total yield, and limited output, and achieve the effects of low cost, low requirements for reaction conditions, and easy operation

Inactive Publication Date: 2015-12-16
台州复瑞生物科技有限公司
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  • Application Information

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Problems solved by technology

[0002] 4-Phenyl-2,7-naphthyridin-1(2H)-one, referred to as LophocladineA(LA), was first extracted from red algae collected in Fiji waters. Cytotoxicity studies have shown that the compound has affinity for NMDA receptors. Moreover, it is a δ-opioid receptor antagonist, which can be used as a potential natural analgesic drug and has a wide range of application values, but it is relatively difficult to extract from red algae and other organisms and the yield is limited
This technique raw material is easy to get, but route step is too many, and total yield is too low (<20%)

Method used

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  • Preparation method for 4-phenyl-2,7-naphthyridine-1(2H)-ketone
  • Preparation method for 4-phenyl-2,7-naphthyridine-1(2H)-ketone
  • Preparation method for 4-phenyl-2,7-naphthyridine-1(2H)-ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] In a 100mL three-necked flask, add 2.8g (12mmol) of the raw material formula II compound 3-amino-4-phenyl-1H-pyran[3,4-c]pyridin-1-one, and then add 30mL of N,N-Dimethylformamide and 60mL concentrated ammonia water (equivalent to 70mmol of ammonia), then reacted at room temperature for 3h, then heated to 90°C for reflux reaction for 6h, after the reaction was completed, then use a rotary evaporator When steaming to a small amount of liquid, add 10mL of water and filter under reduced pressure to obtain 2.5g of yellow solid intermediate compound 3-amino-4-benzene-2,7-naphthyridin-1(2H)-one, the theoretical yield is 2.8g, the final yield mass yield is 89.3%.

[0026] Then take 0.8g (3.4mmol) of the intermediate product formula III compound 3-amino-4-benzene-2,7-naphthyridin-1(2H)-one obtained above and put it into another 100mL three-necked flask, and then add 20mL n-butanol solvent, 30mL of glacial acetic acid and 20mL of water, and then lower the temperature until the t...

Embodiment 2

[0038] In a 100mL three-necked flask, add 2.8g (12mmol) of the raw material formula II compound 3-amino-4-phenyl-1H-pyran[3,4-c]pyridin-1-one, and then add 40mL of THF solvent and 64mL concentrated ammonia water (equivalent to adding 75mmol of ammonia), then reacted at 30°C for 2.5h, then heated to 80°C for reflux reaction for 8h, after the reaction, steamed to an When there is a small amount of liquid, add 10mL of water and filter under reduced pressure to obtain 2.6g of yellow solid intermediate compound 3-amino-4-benzene-2,7-naphthyridin-1(2H)-one, the theoretical yield is 2.8g, The final yield mass yield is 92.9%.

[0039] Then take 0.8g (3.4mmol) of the intermediate product formula III compound 3-amino-4-benzene-2,7-naphthyridin-1(2H)-one obtained above and put it into another 100mL three-necked flask, and then add 30mL ethanol solvent, 50mL of hydrochloric acid aqueous solution with a mass concentration of 30%, and then lower the temperature until the temperature drops ...

Embodiment 3

[0042] In a 100mL three-necked flask, add 2.8g (12mmol) of the raw material formula II compound 3-amino-4-phenyl-1H-pyran[3,4-c]pyridin-1-one, and then add 40mL of Dioxane solvent and concentrated ammonia water, the addition of concentrated ammonia water is to make the amount of ammonia in concentrated ammonia water reach 24mmol, which is equivalent to making the compound of formula Ⅱ: the molar ratio of ammonia in concentrated ammonia water is 1:2, and then at 0 ℃ Under the conditions, the reaction was carried out for 3.5 hours, and then heated to 100°C for reflux reaction for 6 hours. After the reaction, evaporated with a rotary evaporator until there was a small amount of liquid, added 10mL of water and filtered under reduced pressure to obtain 2.55g of yellow solid intermediate product formula Compound III, 3-amino-4-benzene-2,7-naphthyridin-1(2H)-one, has a theoretical yield of 2.8 g and a final mass yield of 91.1%.

[0043] Then take 0.8g (3.4mmol) of the intermediate pr...

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Abstract

The invention relates to a preparation method for 4-phenyl-2,7-naphthyridine-1(2H)-ketone, and belongs to the technical field of medicine synthesis. According to the preparation method for the 4-phenyl-2,7-naphthyridine-1(2H)-ketone, the problems that an existing reaction route is long and low in yield are solved. The preparation method comprises the steps that 3-amino-4-phenyl-1H-pyran-[3,4-c]pyridine-1-ketone reacts with ammonium water to obtain 3-amino-4-benzene-2,7-naphthyridine-1(2H)-ketone; on the acidic condition, a diazo-reaction takes place between the 3-amino-4-benzene-2,7-naphthyridine-1(2H)-ketone and nitrite to obtain a diazotized intermediate product, and after the reaction is completed, the temperature is increased to enable the diazotized intermediate product to be converted into the final product 4-phenyl-2,7-naphthyridine-1(2H)-ketone. The preparation method has the advantages that the raw materials are easy to obtain, the reaction requirements are low, operation is easy, only two steps of reactions are needed, the technology is simplified, and the total yield of the final obtained 4-phenyl-2,7-naphthyridine-1(2H)-ketone is higher.

Description

technical field [0001] The invention relates to a preparation method of 4-phenyl-2,7-naphthyridin-1(2H)-one, which belongs to the technical field of medicine synthesis. Background technique [0002] 4-Phenyl-2,7-naphthyridin-1(2H)-one, referred to as LophocladineA(LA), was first extracted from red algae collected in Fiji waters. Cytotoxicity studies have shown that the compound has affinity for NMDA receptors. Moreover, it is a δ-opioid receptor antagonist, which can be used as a potential natural analgesic drug and has wide application value, but it is relatively difficult to extract from organisms such as red algae and the yield is limited. Therefore, most of them are carried out by artificial synthesis at present. The existing techniques for artificially synthesizing 4-phenyl-2,7-naphthyridin-1(2H)-one mainly contain the following methods: [0003] For example, a novel synthetic method of LophocladineA (LA) (Wannaporn Disadee et al., Tetrahedron Letters, 2011, 52, 6142–...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 朱岩杨小乐吴健勇邱程鹏杨珍珍徐峰吴翰桂
Owner 台州复瑞生物科技有限公司
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