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Coumarinoimidazole derivative or pharmaceutically acceptable salt thereof, and uses of coumarinoimidazole derivative or pharmaceutically acceptable salt thereof

A technology of medicinal salts and halogens, applied in the field of chemical medicine, can solve the problems of low selectivity, damage to normal cells, large toxic side effects, etc.

Inactive Publication Date: 2017-01-04
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the low selectivity of the current first-line anti-tumor chemotherapeutic drugs, while killing tumor cells, it also damages normal cells in the body, thus showing relatively large toxic and side effects, which limits its clinical application.

Method used

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  • Coumarinoimidazole derivative or pharmaceutically acceptable salt thereof, and uses of coumarinoimidazole derivative or pharmaceutically acceptable salt thereof
  • Coumarinoimidazole derivative or pharmaceutically acceptable salt thereof, and uses of coumarinoimidazole derivative or pharmaceutically acceptable salt thereof
  • Coumarinoimidazole derivative or pharmaceutically acceptable salt thereof, and uses of coumarinoimidazole derivative or pharmaceutically acceptable salt thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Compound Ia: the structural formula is Its preparation method is:

[0036] First use the method disclosed in the application number 201310205309.X to prepare the compound

[0037] The preparation method of compound Ia:

[0038] Dissolve 5-phenyl-4-oxo-7-bromo-3,4-dihydroimidazo[4,5-c]coumarin (375 mg, 1 mmol) and potassium tert-butoxide (336 mg, 3 mmol) in In 2mL DMF, slowly add CH dissolved at 0°C dropwise 3 The DMF solution of 2mL of I (142mg, 1mmol), TLC monitors; About 40 minutes, product generation is arranged, but there is reactant, if prolonging reaction time, product changes into by-product, and yield declines; Processing reaction: promptly reacted for 40 minutes After that, the reaction solution was introduced into water for dispersion, extracted three times with ethyl acetate, backwashed three times with saturated saline, dried over anhydrous sodium sulfate, spin-dried, and passed through the column with petroleum ether / ethyl acetate system to obtain 30 ...

Embodiment 2

[0042] Preparation of compound II a: the reaction principle is the same as in Example 1, and the compound is first prepared by the method disclosed in the application number 201310205309.X Referring again to the preparation method of Example 1, compound II a was obtained:

[0043]

[0044] 1 H NMR (400MHz, DMSO) δ7.55(d, J=8.3Hz, 2H), 7.44(dd, J=8.8, 2.3Hz, 1H), 7.37(d, J=2.3Hz, 1H), 7.29(d ,J=8.2Hz,2H),6.84(d,J=8.9Hz,1H),3.49(s,3H),2.18(s,3H),1.66(s,6H),1.23(s,9H)ppm. ESI-MS: 510,512[M+H] + .

Embodiment 3

[0046] Preparation of Compound Ib: Refer to Example 1 for the reaction raw materials.

[0047]

[0048] 1 H NMR (400MHz, DMSO) δ9.14(s, 1H), 8.52(s, 1H), 8.01(t, J=7.8Hz, 2H), 7.83(d, J=10.6Hz, 1H), 7.75(m ,2H),7.63(t,J=7.4Hz,1H),7.40(m,3H),7.30(d,J=7.4Hz,2H),7.05(d,J=8.6Hz,1H),3.63(s ,3H),2.21(s,3H),1.19(s,9H)ppm.

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Abstract

The present invention relates to the technical field of chemical medicine, and particularly relates to an antitumor compound or a pharmaceutically acceptable salt thereof, and uses of the antitumor compound or pharmaceutically acceptable salt thereof. According to the present invention, the provided compound has a structure represented by a formula I, and the pharmacological experiment results show that the compounds provide good inhibitory activity on a variety of tumor cell lines; and the compound provides selective inhibitory activity against colorectal cancer and breast cancer, further can inhibit the formation of the colorectal cancer cell HCT116 cell population, can block the SW620 cell cycle in the G0 / G1 phase, and can concurrently promote the apoptosis of the two colorectal cancer cells such as HCT116 cells and SW620 cells. The formula I is defined in the specification.

Description

technical field [0001] The invention belongs to the technical field of chemistry and medicine, and particularly relates to a coumarinimidazole derivative or a pharmaceutically acceptable salt thereof and its application. Background technique [0002] Cancer is a major disease that endangers human health and has become the number one cause of death in developed and underdeveloped countries in the world today. As the population grows and ages, especially in less developed countries, many unhealthy lifestyles: smoking, poor nutrition, lack of exercise are more likely to cause cancer. According to global cancer statistics, in 2012, the number of new cancer cases in the world is estimated to be 14.1 million, and the death toll will reach 8.2 million. As the world population is aging, the World Health Organization estimates that the number of cancer deaths worldwide is expected to continue to rise and may exceed 13.1 million by 2030. The number of malignant tumor patients in the...

Claims

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Application Information

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IPC IPC(8): C07D491/052A61P35/00A61P35/02
CPCC07D491/052
Inventor 李锐魏于全
Owner SICHUAN UNIV
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