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3-alkoxy substituted-2, 5, 7-tri-substituted benzopyran-4-ketones compounds, preparing method thereof and pharmaceutical compounds containing same
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A benzopyran, trisubstituted technology for medicinal chemistry and pharmacotherapeutics
Inactive Publication Date: 2007-07-04
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI +1
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So far, there is no specific treatment and prevention means for colds and SARS, especially for SARS coronavirus infection, there is no specific antiviral therapy
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[0081] Add 5 g of dendrobetin and 10.5 g of dichlorodiphenylmethane into a 50 ml round bottom flask, heat up to 180° C. and stir for 10 minutes. Cooled to room temperature, the resulting solid was separated by column chromatography (eluent CH 2 Cl 2 / EtOAc=85:15), to obtain 2.7 g of product IV as a yellow solid, with a yield of 39.1%. Mp 239-240°C (lit. 222-224°C).
[0084] 2-(2,2-Diphenyl-benzo[1,3]dioxol-5-yl)-3-O-β-D-tetraacetylglucopyranose-5,7-dihydroxy- Benzopyran-4-one (a kind of compound V)
[0085] Put 0.3 g of IV, 0.13 g of potassiumcarbonate and 0.4 g of tetraacetyl-α-D-glucopyranose into a 50 ml round bottom flask, under the protection of argon, stir at 0°C for 2 hours, turn to room temperature, and stir for 12 hours, An appropriate amount of water was added, extracted with ethyl acetate, dried, and the solvent was evaporated under reduced pressure. The residue was separated by column chromatography (eluent: petroleumether / EtOAc=4:1) to obtain 0.16 g of a yellow solid product, with a yield of 31.2%. MS-ESI 797[M+H] + .
Embodiment 3
[0087] Dendrobetin-3-O-β-D-glucopyranose (compound I A A kind of (I A -1))
[0088] 0.16 g of V-1 and 30 mg of Pd / C (30%) were put into 10 ml of absolute ethanol, and hydrogenolysis was carried out for 24 hours under stirring at room temperature. After filtration, the solvent was evaporated under reduced pressure, and the residue was separated by column chromatography (eluent: petroleumether / EtOAc=2:1) to obtain 62 mg of dendrobetin-3-O-β-D-tetraacetylglucopyranose.
[0089] Put the above product and 8 mg of sodium methylate into 10 mg of anhydrousmethanol, stir at room temperature for 1 hour, add an appropriate amount of cation exchange resin (Dowex 50X4-400), filter, evaporate the solvent under reduced pressure, and dissolve the obtained solid with a small amount of dichloromethane After washing, 22 mg of yellow solid was obtained, with a yield of 23.7% (total yield in two steps). Mp 172-174°C;
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Abstract
The invention relates to a novel 3- alkoxy-substituted- 2, 5, 7- tri-substituted chromene -4-actone, the preparation method and its application in preparing drug that prevent SARS and influenza caused by coronavirus. The general formula of the compound is shown in (me). The compound can be used as dual-effective inhibitor for 3CL proteinenzyme in SARS virus and HCoV- 229E virus with antigens, and then prevent their further replicatioe invention also relates to the medical matter taking said compound as active substance. The medical compound of said compound can precent and treat SARS and influenza.
Description
technical field [0001] The present invention relates to the fields of medicinal chemistry and pharmacotherapeutics, more specifically to 3-alkoxy-substituted-2,5,7-trisubstituted benzopyran-4-one compounds, their preparation methods and pharmaceutical combinations containing such compounds things. The compound can be used for preventing and treating SARS virus and cold virus infection. Background technique [0002] The present invention takes the 3CL protease (3CLPro) of SARS virus and HCoV-229E antigenic cold virus as the target design of a class of 3-alkoxy-substituted-2,5,7-trisubstituted chromen-4-one compounds and its preparation method. The present invention also relates to the application of the compounds as SARS virus and HCoV-229E antigen type cold virus inhibitors in the treatment and / or prevention of SARS virus and cold virus infections. [0003] Coronavirus belongs to Nidovirales (Nidovirales) Coronaviridae (Coronaviridae) Coronavirus (Coronavirus), is a class...
Claims
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