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Benzene sulfonamide derivatives, preparation method, and treatment application
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A technology of benzenesulfonamide and derivatives, which is applied in the field of medicine and can solve problems such as high toxicity
Inactive Publication Date: 2015-03-11
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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[0008] Wortmannin and LY294002 are the first-generation PI3K inhibitors. These two inhibitors are not selective for PI3K, so they are more toxic
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Embodiment 1
[0062] N-(5-(4-(3-(dimethylamino)prop-1-yn-1-yl)quinolin-6-yl)-2-methoxypyridin-3-yl)-2,4 - Difluorobenzenesulfonamide (III, compound number in the table 1 ) preparation
[0063]
[0064] a) Preparation of N-(5-(4-chloroquinolin-6-yl)-2-methoxypyridin-3-yl)-2,4-difluorobenzenesulfonamide (II)
[0065] Dissolve 6-bromo-4-chloroquinoline (2 g, 8.25 mmol) in dioxane (30 mL), add pinacol diborate (2.30 g, 9.07 mmol) and potassium acetate (1.62 g, 16.50 mmol ) and the palladium catalyst PdCl 2 (dppf)CH 2 Cl 2 (0.21g, 0.25mmol), heated to reflux at 100°C for 3h under the protection of nitrogen, the raw material point was detected to disappear, and the reaction was stopped. Add N-(5-bromo-2-methoxypyridin-3yl)-2,4-difluorobenzenesulfonamide (I) (3.4 g, 9.08 mmol) and another part of palladium catalyst PdCl to the mixed system 2 (dppf)CH 2 Cl 2 (0.21 g, 0.25 mmol) and 2M K 2 CO 3 solution (10 mL), heated to reflux at 110° C. for 16 h under nitrogen protection to stop the ...
Embodiment 2-11
[0069] surface 1 Compound 2-11 Can be by corresponding raw material, with reference to preparation embodiment 1 Compounds were prepared by general methods.
Embodiment 12
[0070] Example 12 : The enzyme inhibitory activity assay of this series of compounds:
[0071] The test results of the enzyme inhibitory activity of the above-mentioned compounds are shown in the table 3 , a total of three methods were used in the test:
[0072] Using the method of Lance Ultra Assay to test the IC of mTOR 50 value.
[0073] Using the method of ADP-Glo Luminescent KinaseAssay to test the IC of PI3Kβ and PI3Kγ 50 value.
[0074] Use the method of Kinase-Glo Luminescent KinaseAssay to test the IC of PI3Kα and PI3Kδ 50 value.
[0075] Table 3 IC of some compounds on PI3Kα 50 (nM)
[0076]
[0077] Table 3 It can be seen that all the synthesized compounds have good inhibitory activity on PI3Kα, the best of which is the compound 3 , is 2.0 nM. On this basis, two compounds with better activity were preferred, and their inhibitory activities on mTOR and different subtypes of PI3K were tested, and it was shown that they had inhibitory activit...
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Abstract
The invention relates to the technical field of medicine, and specifically relates to benzene sulfonamide derivatives in different substitution types, wherein the derivatives are represented by the formula (A), and the definitions of each group are listed in the description. The derivatives have an excellent performance on inhibiting the activity of PI3K kinase, and moreover have high antitumor activities on tumors such as human lungcancer, human coloncancer, human livercancer, human breast cancer, and the like. So the derivatives can be used to prepare target antitumor drugs having the advantages of high efficiency, low toxicity, and strong specificity, and thus the derivatives have very good development values. The invention further relates to a composition composed of the derivatives, a preparation method thereof, and applications of the composition in preparation of antitumor drugs.
Description
technical field [0001] The invention relates to the technical field of medicine, and relates to a class of various types of substituted 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. Such compounds exhibit good broad-spectrum inhibitory activity against various tumor cells such as human lung cancer, colon cancer, breast cancer, and liver cancer. Background technique [0002] In recent years, malignant tumors have become the first cause of death among urban and rural residents in my country, and the mortality rate is in...
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