Pharmaceutical use of 6-aryl-3-substituted carbonyl pyridine compound

A technology for compounds, pyridines, used in the fields of medicinal chemistry and pharmacology

Inactive Publication Date: 2010-11-17
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the shortcomings of this screening system are gradually exposed, and the results are somewhat different from those of human tumor cells.

Method used

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  • Pharmaceutical use of 6-aryl-3-substituted carbonyl pyridine compound
  • Pharmaceutical use of 6-aryl-3-substituted carbonyl pyridine compound
  • Pharmaceutical use of 6-aryl-3-substituted carbonyl pyridine compound

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0045] Preparation example 1: Preparation of starting compound IIa (p-methoxyacetophenone):

[0046] Compound IIa

[0047] Methoxybenzene (10.8 g, 0.1 mol) was dissolved in 150 ml of dichloromethane, then anhydrous zinc chloride powder (26.8 g, 0.20 mol) was added, and acetic anhydride (15.3 g, 0.15 moles); after the dropwise addition, the reaction was slowly raised to room temperature for 7 hours, then the reactant was carefully poured into 600 ml of ice water, and extracted 3 times with ethyl acetate; the organic phase was dried with anhydrous magnesium sulfate, filtered and concentrated The crude product was obtained as a colorless oil, and the starting compound IIa (p-methoxyacetophenone) (13.1 g, yield 87%) was obtained by short silica gel column chromatography. White solid, melting point: 35-38°C. H NMR spectrum 1 H-NMR (400MHz, deuterated chloroform, δppm) 2.56 (single peak, 3H, COCH 3 ), 3.87 (single peak, 3H, OCH 3 ), 6.93 (doublet, 2H, J=8.4Hz, H-3,5), 7.94 (...

preparation example 2

[0048] Preparation example 2: Preparation of starting compound IIb (m-methoxyacetophenone):

[0049] Compound IIb

[0050] 3-Hydroxyacetophenone (13.6 grams, 0.1 moles) was dissolved in 150 milliliters of acetone, 20 grams of potassium carbonate (0.15 moles) and dimethyl sulfate (12.6 grams, 0.1 moles) were added; reflux reaction for 10 hours, TLC showed After the reaction was complete, filter, wash the filter cake with ethyl acetate, and concentrate to obtain a crude brown oil, which was subjected to short silica gel column chromatography to obtain Compound IIb (m-methoxyacetophenone), 12.1 g, with a yield of 81%. Colorless oil.

preparation example 3

[0051] Preparation example 3: Preparation of intermediate compound IIIa [3-cyano-6-(4-methoxyphenyl)-2H-pyridin-2-one]:

[0052] Compound IIIa

[0053] Sodium metal (2.76 g, 120 mmol) was added in 250 ml of ether, 1 ml of ethanol was added dropwise, compound IIa (p-methoxyacetophenone) (100 mmol) and ethyl formate ( 150 mmol) mixture, after the dropwise addition, the mixture was stirred for 15 minutes, then warmed up to room temperature and reacted for 1 hour, after diethyl ether was distilled off under reduced pressure, cyanoacetamide (12.6 grams, 150 mmol) and water (400 mmol) were added to the solid mixture. ml). After the mixture was refluxed for 8 hours, cooled, acidified with acetic acid, filtered to obtain a yellow solid, after drying, the initial product was recrystallized from ethanol to obtain intermediate compound IIIa[3-cyano-6-(4-methoxyphenyl) -2H-pyridin-2-one]: yield 56%, light yellow solid; melting point > 250 ° C; R f (Dichloromethane / methanol 20:1) 0....

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Abstract

The present invention provides a class 6-aryl-3-substituted carbonyl-pyridine compound and the application of medicinal salt in anti-tumor medicine preparation. By the pharmacological activity test, the compound has obvious activity inhibiting the growth of vitro human chronic medullary archeocyte leukaemia cell strain (K562) and mouse lymph sample tumor cell train (P388D1) and considerable wide spectrum, which can be used for preparing anti-tumor medicines for leukaemia and relevant tumor diseases.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry and pharmacology, in particular, the invention relates to the use of a class of 6-aryl-3-substituted carbonyl-pyridine compounds for preparing antitumor drugs and pharmaceutical compositions. Background technique [0002] According to the report of the World Health Organization, malignant tumors are common and frequently-occurring diseases that seriously threaten human health. Among the 5 billion people in the world, there are about 9 million new cases every year, and 7 million deaths due to tumors, and there is an increasing trend every year. Drug therapy plays an important role in the three major therapies for malignant tumors. Significant progress has been made in the research of anticancer drugs. In recent years, with the continuous development of molecular oncology and molecular pharmacology, as well as the elucidation of the nature of tumors, the invention and application of advanced tec...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/4725A61K31/4545A61K31/496A61P35/00A61K31/455
Inventor 赵昱孙莲莉杨雷香蒋翔锐阳应华徐艳陶巧凤约阿施·史托克希特
Owner ZHEJIANG UNIV
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