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A kind of quinolinone alkaloid compound and its application as antiviral drug
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A technology of alkaloids and compounds, which can be used in antiviral agents, drug combinations, medical preparations containing active ingredients, etc., and can solve the problem of no vaccine
Active Publication Date: 2019-03-29
YANGZHOU BLUE BIOMEDICAL TECH CO LTD
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Problems solved by technology
There is currently no clinically applicable vaccine, and ribavirin (ribavirin) is the only chemotherapeutic drug used clinically (J.Med.Chem.2008,51,875–896)
Method used
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Embodiment 1
[0047]
[0048] Weigh 500mg of compound 4, dissolve in 20mL acetone, add 150mg Na 2 CO 3 , after stirring at room temperature for half an hour, add 1.0mL MeI, react at 30°C for 4h, TLC detects that the reaction raw materials almost completely disappear, extract twice with ethyl acetate, dry the organic layer with anhydroussodiumsulfate, concentrate, and pass through the silica gel column layer Analysis (eluent is EtOAc / petroleumether=12:1~8:1) to obtain 472 mg of light yellow solid, which is compound 37, yield 92%, ESI-MS m / z: 565.3 [M+H] + , 587.3[M+Na] + .
Embodiment 2
[0050]
[0051] Weigh 10 mg of compound 4, dissolve in 2 mL of dichloromethane, add 3 μL of Ac 2 0, 50 μ L of pyridine, after stirring at room temperature for 2 h, TLC detected that the reaction raw materials almost completely disappeared, added 20 mL of dichloromethane to dilute, washed with water, and the organic phase was dried over anhydroussodiumsulfate, concentrated, and subjected to silica gelcolumn chromatography (eluent: EtOAc / petroleumether=12:1~10:1), to obtain 9.5 mg of a light yellow solid, which is compound 38, with a yield of 88.2%, ESI-MS m / z: 593.3 [M+H] + , 615.3[M+Na] + .
Embodiment 3
[0053]
[0054] Step (1): Weigh 400 mg of compound 37 and dissolve it in 15 mL of methanol, add a catalytic amount of CH 3 Adjust the pH to 9.0-10.0 with ONa, stir and react at room temperature for 2 hours, add a cation exchange resin to adjust the pH to 7.0, remove the cation exchange resin by filtration, and concentrate to obtain 319 mg of a light yellow solid, which is compound 11, with a yield of 99.7%, ESI-MS m / z:474.2[M+Na] + .
[0055]
[0056] Step (2): Weigh Boc-L-valine (300mg, 1.38mmol) and dissolve it in dry toluene (10mL), add DCC (285mg, 1.38mmol), DMAP (7mg, 0.06mmol), and stir at room temperature After 5 minutes, compound 11 (27 mg, 0.06 mmol) was added, heated to 65°C and reacted for 48 hours, filtered, concentrated under reduced pressure, and subjected to silica gelcolumn chromatography (petroleumether / EtOAc=12 / 1) to obtain 35 mg of a light yellow solid , which is compound 30, the yield is 90%, ESI-MS (m / z): 651.3[M+H] + , 673.4[M+Na] + .
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Abstract
The invention relates to a quinolinone alkaloid compound and an application thereof as an antiviral drug, and particularly relates to a compound of formula I-2 and the stereisomer, geometric isomer, solvate, pharmaceutically acceptable slat thereof or the solvate of the salt thereof and an application thereof as an antiviral agent. The quinolinone alkaloid compound provided by the invention has the characteristics of high efficiency and low toxicity as well as the potential that the quinolinone alkaloid compound is developed into an antiviral drug, and particularly can be used for preventing and / or treating the diseases caused by RSV infection.
Description
technical field [0001] The present invention relates to a quinolinone alkaloid compound and a preparation method thereof, and the present invention also relates to the application of the quinolinone alkaloid compound in the preparation of antiviral drugs. In particular, it relates to a quinolinone alkaloid compound with extremely strong inhibitory activity on respiratory syncytial virus (RSV) of Paramyxoviridae and its preparation method and application. Background technique [0002] Respiratory syncytial virus (respiratory syncytial virus, referred to as syncytial virus, RSV, also belongs to Paramyxoviridae), is a kind of RNA virus, belongs to Paramyxoviridae. RSV infection can cause pneumonia and a variety of lower respiratory diseases. Every year, at least 3 million infants and young children worldwide are hospitalized due to RSV virus infection, and at least 160,000 of them die. Therefore, RSV is also known as a child killer (Science, 2013, 342,546 -547). Currently the...
Claims
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Application Information
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