Anti-influenza virus compound and preparation method thereof

An anti-influenza drug and compound technology, applied in the field of medicine, can solve problems such as being unfavorable to the prevention and control of influenza outbreaks, unable to be equipped in primary medical institutions, increasing the economic burden of patients, etc., and achieving the effects of strong activity, low price and simple preparation method.

Active Publication Date: 2018-12-18
CHONGQING MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because it contains multiple chiral centers, the synthesis cost is high and the price is high, which invisibly increases the economic burden of patients, and the price is too high for primary medical institutions to equip, which is not conducive to the prevention and control of influenza outbreaks in the country.

Method used

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  • Anti-influenza virus compound and preparation method thereof
  • Anti-influenza virus compound and preparation method thereof
  • Anti-influenza virus compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] The preparation route of compound (La) is:

[0023]

[0024] The specific process is:

[0025] Preparation of 4-amino-3-(2-n-propyl-1-pentene)methyl benzoate (Sa): 1-bromo-3-n-propyl-1-pentene (6.7mmol) was dissolved in dioxygen Hexacyclic (30mL), stirred at room temperature under nitrogen protection, then added Et 3 N (3.7mL, 26.90mmol), Pd(PPh 3 ) 4 4-amino-3- Methyl iodobenzoate and Ba(OH) 2 ·8H 2 O (6.4g, 20.2mmol) was dissolved in 15ml of dioxane and added to the system, and the mixture was heated to 90°C and stirred for 8 hours. After the reaction solution was cooled down, it was filtered with diatomaceous earth, 40ml of saline was added to the filtrate, extracted with ethyl acetate (3×50mL), dried with anhydrous magnesium sulfate, filtered, concentrated, separated and purified by silica gel column chromatography to obtain Sa (free Colored oil, 76% yield): 1 H NMR (400MHz, CDCl 3 )δ0.81(t, J=7.4Hz, 3H), 0.97(t, J=7.4Hz, 3H), 1.40(m, 2H), 1.54(m 2H), 2....

Embodiment 2

[0028] The preparation route of compound (Lb) is:

[0029]

[0030] The specific process is:

[0031]Preparation of methyl 4-amino-3-(2-ethyl-1-butene)benzoate (Sb): 1-bromo-2-ethyl-1-butene (6.7mmol) was dissolved in dioxane ring (30mL), stirred at room temperature under nitrogen protection, then added Et 3 N (3.7mL, 26.90mmol), Pd(PPh 3 ) 4 4-amino-3- Methyl iodobenzoate and Ba(OH) 2 ·8H 2 O (6.4g, 20.2mmol) was dissolved in 15ml of dioxane and added to the system, and the mixture was heated to 90°C and stirred for 8 hours. After the reaction solution was cooled down, it was filtered with diatomaceous earth, 40ml of saline was added to the filtrate, extracted with ethyl acetate (3×50mL), dried with anhydrous magnesium sulfate, filtered, concentrated, separated and purified by silica gel column chromatography to obtain Sb (free Colored oil, 73% yield): 1 H NMR (400MHz, CDCl 3 )δ0.97(t, J=7.6, 3H), 1.14(t, J=7.4Hz, 3H), 2.08(q, J=7.4Hz, 2H), 2.23(q, J=7.6Hz, 2H), ...

Embodiment 3

[0034] The preparation route of compound (I) is:

[0035]

[0036] The specific process is:

[0037] Preparation of 4-acetamido-3-(2-n-propyl-1-pentene)benzoic acid (I): Dissolve La (61mg, 0.2mmol) in 2ml methanol, add 2ml 1Mol / L sodium hydroxide . The mixture was stirred at room temperature for 2-3 hours, and the pH of the solution was adjusted to 2 with 1Mol / L hydrochloric acid. After the mixture was evaporated to dryness, the solid residue was dissolved with 3ml of methanol, filtered, and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain I (white solid, yield 61%): m.p.110-111°C, 1 H NMR (400MHz, CDCl 3 )δ0.80(t, J=7.3Hz, 3H), 1.01(t, J=7.2Hz, 3H), 1.39(m, 2H), 1.59(m, 2H), 1.94(t, J=7.3, 2H ), 2.19(s, 3H), 2.24(t, J=7.3Hz, 2H), 6.09(s, 1H), 7.51(s, 1H), 7.83(s, 1H), 8.00(d, J=8.4Hz , 1H), 8.45 (d, J=8.4Hz, 1H); MS (ES) m / z 290 (M+1).

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Abstract

The invention provides an anti-influenza virus compound. The compound is a benzoic acid derivative, compared with the active compound on the market, the active compound of the anti-influenza virus compound has no chiral center, and the synthesis is simpler; the raw material is simple and easy to obtain, the market supply is more, and the price is low. Through an in-vitro neuraminidase-specific fluorogenic substrate 2'-4-methylumbelliferone-a-N-acetylneuraminic acid test, the anti-influenza virus compound has strong anti-H3N2 influenza activity and strong Anti-H1N1 influenza activity, has better therapeutic effect on influenza B, and is expected to develop anti-influenza virus drugs. The preparation method of the invention is simple, and suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to an anti-influenza virus compound and a preparation method thereof. Background technique [0002] Influenza is a global infectious disease caused by influenza virus, and it is also a highly contagious and fast-spreading disease. It is mainly transmitted through droplets in the air, contact between people or contact with contaminated items; typical clinical symptoms are: sudden onset of high fever, general pain, significant fatigue and mild respiratory symptoms. Generally, autumn and winter are the high-incidence period, and the complications and death caused by it are very serious. The disease is caused by influenza virus and can be divided into three types: A (A), B (B) and C (C). Influenza A virus is further divided into subtypes according to the type of protein on the surface of the virus and the combination, including A H1N1, H3N2 and so on. H is called hemagglutinin, an...

Claims

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Application Information

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IPC IPC(8): C07C233/54C07C235/16C07C229/60C07C227/16C07C231/12C07C231/02A61P31/16
CPCC07C227/16C07C229/60C07C231/02C07C231/12C07C233/54C07C235/16
Inventor 李雁武王敬胡叶敏
Owner CHONGQING MEDICAL UNIVERSITY
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