Sulfonamide aryl acetylene compound and use thereof

A technology of aryl alkyne and sulfonamide, applied in the field of sulfonamido aryl alkyne compounds, can solve the problems of anemia, damage, leukopenia and the like

Active Publication Date: 2016-07-06
GUANGZHOU INST OF BIOMEDICINE & HEALTH CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, traditional chemotherapy can cause side effects such as leukopenia, thrombocytopenia, anemia, hair loss, nausea, vomiting and severe liver damage

Method used

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  • Sulfonamide aryl acetylene compound and use thereof
  • Sulfonamide aryl acetylene compound and use thereof
  • Sulfonamide aryl acetylene compound and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0165] N-(2,4-difluoro-3-((3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)ethynyl)phenyl)pyridine-3-sulfonamide

[0166] N-(2,4-difluoro-3-((3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)ethynyl)phenyl)pyridine-3-sulfonamide .

[0167]

[0168] Synthesize according to the route of scheme A below:

[0169]

[0170] Step 1: Synthesis of 5-bromo-3H-pyrazolo[3,4-b]pyridin-3-one

[0171] In a 1000ml flask, add 50g (200mmol) of 5-bromo-2-chloronicotinic acid methyl ester, 500ml ethanol, 800mmol of 80% hydrazine hydrate, and reflux for 12h under stirring. During the reaction, solids are precipitated. After the reaction, cool to room temperature , add 1000ml of ice water, wait for the solid to fully separate out and then suction filter, the filter cake is fully washed with water and then vacuum-dried to obtain 36g of light yellow solid with a yield of 85%. Product MS (ESI), m / z: 212, 214 (M + +H + ).

[0172] Step 2: Synthesis of 5-bromo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-...

Embodiment 2

[0189] N-(2,4-difluoro-3-((3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)ethynyl)phenyl)propane-1-sulfonamide

[0190] N-(2,4-difluoro-3-((3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)ethynyl)phenyl)propane-1-sulfonamide

[0191]

[0192] Synthesize according to the route of scheme B below:

[0193]

[0194] Step 10: Synthesis of N-(2,4-difluorophenyl)propane-1-sulfonamide

[0195] In a 250ml round-bottomed flask, dissolve 3g (19.6mmol) 3-ethynyl-2,4-difluoroaniline (prepared according to the above method) in 150ml dichloromethane, drop 3g (21.5mmol, 1.1eq) propanesulfonyl chloride, 2.3ml (29.4mmol, 1.5eq) pyridine, catalytic amount of 4-N,N dimethylaminopyridine, reflux overnight. After the reaction was detected by thin-layer chromatography, add 5ml of 6N hydrochloric acid and appropriate amount of water, extract three times with dichloromethane, wash the organic phase with dilute hydrochloric acid and saturated saline once, dry with anhydrous sodium sulfate, evaporate the sol...

Embodiment 3

[0200] N-(3-((1H-pyrazolo[3,4-b]pyridin-5-yl)ethynyl)phenyl)propane-1-sulfonamide

[0201] N-(3-((1H-pyrazolo[3,4-b]pyridin-5-yl)ethynyl)phenyl)propane-1-sulfonamide

[0202]

[0203] The synthesis method is as in Example 2.

[0204] Product characterization: 1 HNMR (400MHz, DMSO-d 6 ):δ(ppm)13.91(s,1H),9.98(s,1H),8.69(d,J=2Hz,1H),8.50(d,J=1.8Hz,1H),8.20(s,1H), 7.38-7.42(m,2H),7.32(d,J=7.8Hz,1H),7.27(dd,J=1.9,7.1Hz,1H),3.12(t,J=7.6Hz,2H),1.67-1.74 (m,2H),0.95(t,J=7.4Hz,3H).MS(ESI),m / z:341(M + +H + ).

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Abstract

The present invention discloses a sulfonamide aryl acetylene compound having structure characteristics of formula I and a use thereof, and belongs to the technical field of chemical medicines. The compound has an activity of targetedly inhibiting protein kinase, and is able to conduct target treatment of hyperproliferative diseases in human, other mammal tumors, etc. caused by abnormal protein kinase.

Description

technical field [0001] The invention relates to the technical field of chemistry and medicine, in particular to a sulfonamide aryl alkyne compound and its application. Background technique [0002] Tumor is a disease that seriously threatens human health and life, and its incidence rate is second only to cardiovascular diseases. And with the impact of environmental pollution, food safety and other issues, the incidence of malignant tumors is rapidly increasing. According to the data released by the World Health Organization in 2003, there were 10 million malignant tumor patients in the world in 2000, and 6.2 million deaths due to malignant tumors, accounting for 12% to 25% of the total deaths. It is estimated that by 2020, there will be 15 million new cases worldwide each year. [0003] In tumor treatment, traditional chemotherapy mainly targets tumor cells with faster metabolism through cytotoxicity. However, in addition to tumor cells, some normal cells in the normal bo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C07D213/73C07D231/56C07D487/04C07D401/12A61P35/00A61P35/02
Inventor 丁克李迎君程辉敏任小梅张章庄晓曦龙活尤涂正超
Owner GUANGZHOU INST OF BIOMEDICINE & HEALTH CHINESE ACAD OF SCI
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