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Spiro indolone compounds, a preparing method, a medicine composition and uses of the compounds

A spiroindolinone and compound technology, applied in the field of spiroindolinone compounds, can solve the problems of low selectivity and low inhibitory activity of antitumor drugs

Active Publication Date: 2017-06-06
SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The technical problem to be solved by the present invention is to provide a spirocyclic indolone compound, preparation method, pharmaceutical composition and use in order to overcome the defects of low selectivity and low inhibitory activity of antitumor drugs in the prior art.

Method used

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  • Spiro indolone compounds, a preparing method, a medicine composition and uses of the compounds
  • Spiro indolone compounds, a preparing method, a medicine composition and uses of the compounds
  • Spiro indolone compounds, a preparing method, a medicine composition and uses of the compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0158] Example 1 Preparation of 5'-phenyl-3'H-spiro[indoline-3,2'-[1,3,4]thiadiazol]-2-one

[0159]

[0160] Thiobenzohydrazide (1.52g, 0.01mol) and isatin (1.47g, 0.01mol) were dissolved in ethanol (50ml), heated to 40°C for 1 hour. TLC monitored the completion of the reaction. The reaction solution was concentrated and filtered. The filtered solid was recrystallized from ethyl acetate to obtain the target product with a yield of 76% and a purity of 99% by HPLC.

[0161] 1 H NMR (300MHz, DMSO-d 6 )δ10.5(s,1H),8.88(s,1H),7.61-7.37(m,6H),7.31(t,J=7.2Hz,1H),7.05(t,J=7.8Hz,1H), 6.86(d,J=7.8Hz,1H); MS(ESI + )m / z 304(M+23)

Embodiment 2

[0162] Example 2 Preparation of 4-chloro-5'-phenyl-3'H-spiro[indoline-3,2'-[1,3,4]thiadiazol]-2-one

[0163]

[0164] Replace isatin with 4-chloroisatin, and the remaining required raw materials, reagents and preparation methods are the same as in Example 1 to obtain the product 4-chloro-5'-phenyl-3'H-spiro[indoline-3 ,2'-[1,3,4]thiadiazol]-2-one, yield 75%, HPLC purity 99%.

[0165] 1 H NMR (300MHz, DMSO-d 6 )δ10.84(s,1H),8.71(s,1H),7.56-7.40(m,5H),7.32(t,J=7.5Hz,1H),7.06(d,J=8.4Hz,1H), 6.86(d,J=8.4Hz,1H); MS(ESI + )m / z 338(M+23),354(M+39),370(M+55).

Embodiment 3

[0166] Example 3 Preparation of 5-chloro-5'-phenyl-3'H-spiro[indoline-3,2'-[1,3,4]thiadiazol]-2-one

[0167]

[0168] Replace isatin with 5-chloroisatin, and the rest of the required raw materials, reagents and preparation methods are the same as in Example 1 to obtain the product 5-chloro-5'-phenyl-3'H-spiro[indoline-3 ,2'-[1,3,4]thiadiazol]-2-one, yield 80%, HPLC purity 99%.

[0169] 1 H NMR (300MHz, DMSO-d 6 )δ10.66 (s, 1H), 8.90 (s, 1H), 7.60-7.40 (m, 6H), 7.36 (d, J = 8.4Hz, 1H), 6.88 (d, J = 8.4Hz, 1H); MS (ESI + )m / z 338(M+23).

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Abstract

Spiro indolone compounds, a preparing method, a medicine composition and uses of the compounds are disclosed. In particular, the invention provide spiro indolone compounds shown as a formula I or II, a preparing method of the spiro indolone compounds and uses of the compounds in preparation of antitumor medicines. The compounds have a spiro indolinone skeleton, and the preparing method and potential uses of the compounds have not been reported before. The compounds have obvious killing functions for human cancer cells, particularly a human breast cancer cell strain MDA-MB-231, a human cervical cancer cell strain HeLa or a human lung cancer cell strain A549, have high selectivity, have potentials as novel antitumor medicines and have a good market prospect.

Description

technical field [0001] The present invention relates to spiro indolinone compound, preparation method, pharmaceutical composition and application. Background technique [0002] Malignant tumor is a major disease that threatens human health. Its incidence rate ranks second among the ten major diseases, and its incidence rate is still on the rise with the influence of various factors. At present, 20% of new cancer patients in the world are in China, and 24% of cancer deaths are in China. Due to the shortcomings of drug resistance, drug resistance, time-dependence of drug effect and obvious side effects of cancer drugs in clinical use at present, finding drugs with novel structures has become an urgent problem to be solved. [0003] Apoptosis (also known as programmed cell death in some cases) is a normal death mechanism to remove senescent cells or abnormal cells, and the disorder of this mechanism is directly related to the occurrence of various diseases. Since the 1990s, p...

Claims

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Application Information

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IPC IPC(8): C07D513/10C07D487/10A61K31/433A61K31/4162A61P35/00
CPCC07D487/10C07D513/10
Inventor 王任小吕龙冯骁周宓李杨峰李晴
Owner SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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