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N-(5-(quinolyl-6-yl) pyridyl-3-yl)benzsulfamide derivatives, and preparation method and treatment use thereof
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A technology of difluorobenzenesulfonamide and methoxypyridine, which is applied in the field of medicine and can solve the problems of low selectivity and large side effects
Inactive Publication Date: 2014-05-14
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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However, traditional cytotoxic antitumor drugs have serious shortcomings such as low selectivity and large side effects. PI3K inhibitors can target tumor cells, which is expected to reduce the above shortcomings
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Embodiment 1
[0128] N-(5-(4-(1H-1,2,4-triazol-1-yl)quinolin-6-yl)-2-methoxypyridin-3-yl)-2,4-di The preparation of fluorobenzenesulfonamide (IV, compound number 1 in the table):
[0129]
[0130] a) Preparation of 6-bromo-4-(1H-1,2,4-triazol-1-yl)quinoline (III):
[0131] Add 6-bromo-4-chloroquinoline (0.5g, 2.06mmol) and triazole (0.71g, 10.30mmol) into a 25ml single-necked bottle, dissolve in 4mL of 1,4-dioxane, and reflux at 90°C Stir and heat for 4 hours, cool to room temperature, add chloroform and saturated sodiumbicarbonate solution for extraction, wash the organic layer with water and saturated brine respectively, dry over anhydrousmagnesiumsulfate, and evaporate to dryness under reduced pressure, 0.24 g of the solid product crystallized with ether, yield rate of 42.9%. MS (ESI) m / z: 275.16 (M+H+).
[0132] B) N-(5-(4-(1H-1,2,4-triazol-1-yl)quinolin-6-yl)-2-methoxypyridin-3-yl)-2,4 - Preparation of difluorobenzenesulfonamide (IV, compound number 1 in the table):
[0133]...
Embodiment 2-3
[0135] Compounds 2 and 3 in Table 1 can be prepared from corresponding raw materials by referring to the general method for preparing the compound of Example 1.
Embodiment 4
[0137] N-(5-(4-chloroquinolin-6-yl)-2-methoxypyridin-3-yl)-2,4-difluorobenzenesulfonamide (IV, compound number 4 in the table)
[0138]
[0139] a) Preparation of 4-chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline (HI):
[0140] Add raw material (II) (0.50g, 2.06mmol) in the 50ml eggplant-shaped bottle, dissolve with 13mL of dioxane, add biboronic acid pinacol ester (0.79g, 3.10mmol) and potassium acetate (0.81g , 8.25mmol) and palladium catalyst PdCl 2 (dppf)CH 2 Cl 2 (0.128g, 0.157mmol), heated at 90°C for 3 hours under nitrogen protection. After cooling to room temperature, the solvent was evaporated to dryness, and the resulting mixture was extracted with ethyl acetate (20 mL) and water (20 mL). The aqueous layer was extracted with a small amount of ethyl acetate (15mL×2), the organic layers were combined, dried over anhydroussodiumsulfate, and concentrated to obtain 1.15g of crude product (PH=6), which was purified by silica gel column chromatograp...
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Abstract
The invention relates to the technical field of medicine, and concretely relates to various different types substituted N-(5-(quinolyl-6-yl) pyridyl-3-yl)benzsulfamide derivatives represented by formula (1) (all groups in the formula (1) are defined in the specification. The above compounds have a good antitumor activity against a plurality of tumors comprising human lungcancer, colon cancer, liver cancer, breast cancer, cerebral astrocytoma and the like, lays a foundation for the development of antitumor medicines having the advantages of high efficiency, low toxicity and strong specificity, and has a very good exploitation value. The invention also relates to a composition containing the compounds, a preparation method of the composition, and a use of the composition in the preparation of the antitumor medicines.
Description
technical field [0001] The invention relates to the technical field of medicine, and relates to a class of various types of substituted N-(5-(quinolin-6-yl)pyridin-3-yl)benzenesulfonamide derivatives, a preparation method and a composition. The present invention also relates to the use of such compounds in the preparation of therapeutic drugs for one or more of the following diseases: autoimmune diseases, inflammatory diseases, cardiovascular diseases, neurodegenerative diseases, allergies, asthma, pancreatitis , multiple organ failure, kidneydisease, platelet aggregation, cancer, spermmotility, transplant rejection, graft rejection, and lung injury, especially cancer. These compounds exhibit good broad-spectrum inhibitory activity against various tumor cells such as human lung cancer, colon cancer, liver cancer, breast cancer, and colon cancer. Background technique [0002] Phosphatidylinositol-3-kinases (PI3K) is a member of the lipid kinase family, which can regulate c...
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