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Benzothiazole compound and medical application

A technology of benzothiazole and compound, applied in the field of medicinal chemistry, can solve problems such as small toxic and side effects

Active Publication Date: 2021-05-18
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, so far, no small-molecule regulators of USP7 C-terminal protein have been reported. It is of great significance to develop small-molecule regulators of USP7 C-terminal domain with high activity and less toxic side effects.

Method used

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  • Benzothiazole compound and medical application
  • Benzothiazole compound and medical application
  • Benzothiazole compound and medical application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] N-(2-(furan-2-carboxamide)benzo[d]thiazol-6-yl)isonicotinamide (Compound 1)

[0067]

[0068] Dissolve 2-amino-6-nitrobenzothiazole (1a, 1.0g, 5.13mmol) in pyridine (20mL), add fresh furoyl chloride (758μL, 7.70mmol) dropwise, heat up to 40°C and stir 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 product of intermediate 1b, which was directly used in the next step without purification.

[0069] 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 diatomaceous earth, and the filtrate was evaporated...

Embodiment 2

[0072] N-(2-(furan-2-carboxamide)benzo[d]thiazol-6-yl)pyridineamide (Compound 2)

[0073]

[0074] 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] - .

Embodiment 3

[0076] N-(2-(furan-2-carboxamide)benzo[d]thiazol-6-yl)pyrazine-2-carboxamide (compound 3)

[0077]

[0078] 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 as shown in a formula I and medical application thereof, and particularly relates to a benzothiazole USP7 C-terminal structural domain regulating agent compound or pharmaceutically acceptable salt or ester or solvate thereof as well as a preparation method and application of the benzothiazole USP7 C-terminal structural domain regulating agent compound. The compound or the pharmaceutically acceptable salt or ester or solvate thereof has very strong binding force with USP7 C-terminal protein, has a regulation effect on a USP7 C-terminal structural domain, and has remarkable anti-tumor cell proliferation effect and anti-inflammatory activity; and the compound can be used for preparing medicines for preventing or treating myelodysplastic syndromes, malignant tumors, inflammations or autoimmune diseases.

Description

technical field [0001] The present invention relates to the field of medicinal chemistry, in particular to benzothiazole compounds and their use in pharmaceuticals, in particular to benzothiazole compounds as USP7 C-terminal domain regulators and their use in the prevention and treatment of myelodysplastic syndrome, malignant Use in tumor, inflammatory or autoimmune diseases. 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 prevalen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/14C07D417/12A61K31/4439A61K31/454A61K31/497A61K31/428A61K31/496A61K31/4725A61K31/5377A61K31/4709A61P35/00A61P35/02
CPCC07D417/14C07D417/12A61P35/00A61P35/02
Inventor 孙宏斌陈彩萍周鑫煜刘胜杰袁浩亮温小安
Owner CHINA PHARM UNIV
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