Thiourea compounds and preparation method and application thereof
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A compound, thiourea technology, applied in the field of biomedicine
Inactive Publication Date: 2019-07-05
MEDICINE & BIOENG INST OF CHINESE ACAD OF MEDICAL SCI
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One group of thiourea compounds described in the present invention has no domestic and foreign related literature reports
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Embodiment 1
[0057] , the synthesis of 1-(4-hydroxyl-benzyl)-3-(3-methoxy-4-oxazol-5-yl-phenyl)-thiourea (1)
[0058] In a 25ml flask, the compound 3-methoxy-4-(oxazol-5-yl)aniline (1.0mmol) and 1,1'-thiocarbonyldiimidazole (TCDI, 1.1mmol) were dissolved in anhydrous tetrahydrofuran (THF, 4.0 mL) was stirred at room temperature for 2 hours, 4-hydroxy-benzylamine (2.0 mmol) was added and then 4-dimethylaminopyridine (DMAP, 0.1 mmol) was added to the solution. The mixture was further stirred overnight at reflux temperature. The solvent was removed under reduced pressure. Extracted with ethyl acetate (3 x 20 mL), the organic layer was separated, washed with saturated aqueous potassium bisulfate solution and water, then dried over anhydrous sodium sulfate. The solvent was removed in vacuo, and the residue was purified by flash chromatography on silica gel, eluting with a gradient of 30-60% ethyl acetate in petroleum ether, to afford compound 1. Pale yellow solid, yield 35%. 1 H-NMR (500MHz...
Embodiment 2
[0059] , the synthesis of 1-(4-methoxy-benzyl)-3-(3-methoxy-4-oxazol-5-yl-phenyl)-thiourea (2)
[0060] Using 3-methoxy-4-(oxazol-5-yl)aniline and 4-methoxy-benzyl as starting materials, compound 2 was obtained according to the similar method of Example 1. White solid, yield 37%. 1 H-NMR (500MHz, DMSO-d 6 )δ (ppm): 10.15 (1H, s), 8.55 (1H, s), 8.40 (1H, s), 7.62 (1H, d, J = 8.5Hz), 7.59 (1H, d, J = 1.0Hz) ,7.46(1H,s),7.30(2H,d,J=8.5Hz),7.13(1H,dd,J 1 =8.5Hz,J 2 =1.0Hz), 6.91(2H,d,J=8.5Hz), 4.68(2H,s), 3.89(3H,s), 3.74(3H,s).
[0062] Using 3-methoxy-4-(oxazol-5-yl)aniline and 3,4-dimethoxy-benzylamine as raw materials, according to the similar method of Example 1, compound 3 was obtained. White solid, yield 37%. 1 H-NMR (500MHz, DMSO-d 6 )δ (ppm): 9.82 (1H, s), 8.40 (1H, s), 8.29 (1H, s), 7.63 (1H, d, J = 8.5Hz), 7.50 (1H, s), 7.47 (1H, s),7.10(1H,d,J=8.5Hz),7.02(1H,s),6.93(1H,d,J=8.5Hz),6.90(1H,d,J=8.5Hz),4.66(2H, s), 3.89(3H,s), 3.76(3H,s), 3.74(3H,s).
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Abstract
The invention discloses a group of thiourea compounds and a preparation method and application thereof. The oxazole phenylthiourea compound or a pharmaceutically acceptable salt thereof has a structure represented by the general formula (I). According to the present inventors, a class of compounds having both IMPDH inhibitory activity and broad-spectrum antiviral activity and pharmaceutical saltsthereof are screened and obtained by studying the structure-activity relationship and the action mechanism of active compounds, wherein the virus comprises influenza virus, hepatitis B virus, coxsackie virus and herpes simplex virus. The invention lays a foundation for the development and application of the compounds as antiviral and other related drugs and pharmaceutical compositions thereof, andprovides a new technical means for antiviral treatment.
Description
technical field [0001] The invention relates to a group of oxazole phenylthiourea compounds, a preparation method of the compounds and their IMPDH inhibitory activity and antiviral activity. The invention belongs to the field of biomedicine. Background technique [0002] Viral infections pose a threat to every living organism in all domains of life. At present, the antiviral drugs used clinically all target viral proteins, and the mechanism of action is to inhibit the replication of the virus or block the invasion of the virus. Viruses rely on continuous mutation to escape drug attacks. Drugs targeting viral proteins all cause virus mutation and drug resistance, which has become a worldwide problem. Influenza is an infectious disease caused by various types of influenza viruses and is characterized by a highly contagious acute respiratory syndrome. Seasonal influenza outbreaks occur around the world each year, causing approximately 3 to 5 million cases of severe illness a...
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