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2-substituted-5-phenyl furan compound, and preparation method, pharmaceutical composition and application thereof
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A technology of phenylfuran and compounds, applied in the field of preparation of B-Raf kinase inhibitors, can solve problems such as inability to achieve effective concentration, poor bioavailability, and no effect on melanoma
Inactive Publication Date: 2014-01-15
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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Therefore, the bioavailability of these inhibitors is poor or the B-Raf V600E The selectivity is not high, which greatly limits their application in the treatment of various tumors
For example, although Sorafenib has good effects on liver cancer and kidneycancer, it has no effect on melanoma. The main reason is that it cannot reach an effective concentration in melanoma cells to inhibit B-Raf V600E active
[0006] In addition, although many studies have reported that B-Raf V600E Mutations play a key role in the pathogenesis of various tumors, but the specific signaling pathways that cause tumor cellcarcinogenesis are still in the preliminary research stage, and the specific mechanism is still unclear. The new B-Raf V600E Specific inhibitors can be used to study the pathogenesis of melanoma, and have important scientific significance and application prospects for the diagnosis and treatment of tumors in future clinical applications
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[0145] Add 100mg of 5-(4-nitrophenyl)-furan-2-carbaldehyde and 1 equivalent of thiobarbituric acid to 2mL of glacial acetic acid, heat up to 90°C and react for 1-2 hours, there are a lot of orange solids Precipitate. The purer crude product can be obtained by suction filtration, and the crude product is fully washed with methanol to obtain the pure compound 5-(5-(4-nitrophenyl)-furan-2-enyl)-2-thiobarbituric acid 136mg, yield 86%.
[0146] 1 H NMR(400MHz,DMSO)δ12.50(s,1H),12.44(s,1H),8.60-8.58(d,J=4.0Hz,1H),8.48-8.35(d,J=8.5Hz,2H) ,8.24-8.21(d,J=8.6Hz,2H),8.12(s,1H),7.74-7.72(d,J=4.0Hz,1H).ESI-MS m / z:344.0[M+H] + .
Embodiment 2
[0147] Example 2: 5-(5-(4-chlorophenyl)-furan-2-enyl)-2-thiobarbituric acid (BBT02)
[0148] Using 5-(4-chlorophenyl)-furan-2-carbaldehyde instead of 5-(4-nitrophenyl)-furan-2-carbaldehyde as raw material, it was prepared according to the method in Example 1.
[0149] 1 H NMR(400MHz,DMSO)δ12.44(s,1H),12.38(s,1H),8.61-8.60(d,J=4.0Hz,1H),8.11(s,1H),8.03-7.99(d, J=8.6Hz,2H),7.63-7.60(d,J=8.6Hz,2H),7.55-7.53(d,J=4.0Hz,1H).ESI-MS m / z:333.0[M+H] + .
Embodiment 3
[0150] Example 3: 5-(5-(2-nitrophenyl)-furan-2-enyl)-2-thiobarbituric acid (BBT03)
[0151] Use 5-(2-nitrophenyl)-furan-2-carbaldehyde instead of 5-(4-nitrophenyl)-furan-2-carbaldehyde as raw material, and prepare according to the method in Example 1.
[0152] 1 H NMR(400MHz,DMSO)δ12.51(s,1H),12.45(s,1H),8.61-8.60(d,J=4.0Hz,1H),8.09-8.03(t,J=8.3Hz,2H) ,7.89(s,1H),7.88-7.83(t,J=8.3Hz,1H),7.78-7.74(t,J=8.3Hz,1H),7.42-7.40(d,J=4.0Hz,1H). ESI-MS m / z:344.0[M+H] + .
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Abstract
The invention relates to the fields of medicinal chemistry and chemical treatment. Specifically, the invention provides a 2-substituted-5-phenyl furan compound represented by the following general formula I, or a cis-trans isomer or a pharmaceutically acceptable salt, an ester, a prodrug or a solvate thereof, and a preparation method, a pharmaceutical composition and an application thereof in preparation of a B-Raf kinase inhibitor. The compound or the pharmaceutical composition thereof can be used as the high-efficiency B-Raf kinase inhibitor used for treating tumor diseases.
Description
technical field [0001] The present invention relates to the fields of medicinal chemistry and chemotherapeutics. Specifically, the present invention relates to 2-substituted-5-phenylfuran compounds or their cis-trans isomers or pharmaceutically acceptable salts, esters, prodrugs or solvates thereof, their preparation methods, and pharmaceutical compositions and its use in the preparation of B-Raf kinase inhibitors. The compound or its pharmaceutical composition can be used as a high-efficiency B-Raf kinase inhibitor for treating tumor diseases. Background technique [0002] The incidence of tumors worldwide is increasing year by year. Because of its high degree of malignancy, early and extensive metastasis, and strong resistance to conventional radiotherapy, it is quite difficult in clinical treatment. Tumor occurrence is a multi-gene, multi-stage process, which may be due to cell cycle dysregulation or abnormal apoptosis process. In this process, Raf kinase, the expressi...
Claims
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