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Benzothiazole compounds and medical application
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A technology of benzothiazole and compounds, applied in the field of medicinal chemistry, to achieve the effects of cheap raw materials, easy large-scale production, and easy availability of raw materials
Inactive Publication Date: 2020-10-13
CHINA PHARM UNIV
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So far, there are no reports of compounds that bind to the USP7 C-terminal protein. Therefore, it is urgent to develop USP7 C-terminal domain regulators with high activity and low toxicity, which can be potentially used in the treatment of diseases such as myelodysplastic syndrome and malignant tumors.
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[0069] Dissolve 2-amino-6-nitrobenzothiazole 1a (1g, 5.13mmol) in pyridine solution (20mL), add fresh furan-2-formyl chloride (758μL, 7.70mmol) dropwise, and heat up to Stir at 40°C for 8 hours. TLC monitored the completion of the reaction and added 1N hydrochloric acid (30 mL) for neutralization, and a large amount of solid precipitated out. After suction filtration, the solid was washed with a small amount of ethyl acetate (2 mL×3) to obtain the crude intermediate 1b, which was directly used in the next step without purification.
[0070] All the obtained crude intermediate 1b was added to methanol (25 mL), 10% palladium / carbon (100 mg) was added, hydrogen gas was introduced and stirred at 50° C. for 7 hours. TLC monitored that the reaction was complete and stopped heating. After cooling to room temperature, the solution was filtered with ...
[0075] Referring to the method of Example 1, isonicotinic acid was replaced by picolinic acid to obtain compound 2 (off-white solid): 1 HNMR (300MHz, DMSO-d 6 )δ12.80(s,1H),10.80(s,1H),8.77(d,J=4.7Hz,1H),8.60(s,1H),8.20(d,J=7.9Hz,1H),8.15– 8.01(m,2H),7.95(d,J=8.9Hz,1H),7.84–7.60(m,3H),6.77(s,1H).ESI-MS m / z 363.1[M-H] - .
[0079] Referring to the method of Example 1, isonicotinic acid was replaced by pyrazine-2-carboxylic acid to obtain compound 3 (off-white solid): 1 H NMR (300MHz, DMSO-d 6 )δ12.83(s,1H),10.88(s,1H),9.33(s,1H),8.95(s,1H),8.83(s,1H),8.57(s,1H),8.04(s,1H ), 7.94(d, J=8.9Hz, 2H), 7.86–7.48(m, 2H), 6.76(s, 1H). ESI-MS m / z 364.1[M-H] - .
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Abstract
The invention discloses a benzothiazole compound and medical application thereof, particularly relates to a benzothiazole compound shown as a formula I and medical application thereof, and especiallyrelates to application of the benzothiazole compound serving as a USP7C-terminal structural domain regulating agent in medicines for preventing and treating myelodysplastic syndromes and malignant tumors. The benzothiazole compound shown in the formula I or the pharmaceutically acceptable salt or solvate of the benzothiazole compound has strong binding force with USP7C-terminal protein; and the protein level of DNMT1 in tumor cells can be reduced, so that the compound can be applied to the preparation of USP7 regulators, has a remarkable anti-tumor cell proliferation effect, and can be used for preparing medicines for preventing or treating myelodysplastic syndrome and malignant tumors.
Description
technical field [0001] The present invention relates to the field of medicinal chemistry, in particular to benzothiazole compounds and their use in pharmaceuticals, especially to benzothiazole compounds and their use as USP7 C-terminal domain regulators in the prevention and treatment of myelodysplastic syndromes and malignant tumors use in . Background technique [0002] Myelodysplastic syndromes (myelodysplastic syndromes, MDS) are a group of heterogeneous myeloid clonal diseases originating from hematopoietic stem cells, characterized by abnormal differentiation and development of myeloid cells, manifested as ineffective hematopoiesis, refractory cytopenias, high Risk of conversion to acute myeloid leukemia (AML). The main causes of death of the patients were the complications caused by the disease itself and the death caused by transformation to AML (Cancer 2010,16:2174-2179). According to statistics, in the United States, its prevalence rate is about 0.004-0.005%, and...
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