Use of aryl-3-substituted carbonyl pyridone compound

A technology of pyridone and compound, applied in the direction of active ingredients of heterocyclic compounds, drug combinations, antineoplastic drugs, etc.

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

AI Technical Summary

Problems solved by technology

However, the variability (Heterogeneity) of cancer cells seems to overcome the impact of this drug. The longer you take this drug, the easier it is to produce cancer cell lines that are resistant to this drug. one of the problems solved

Method used

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  • Use of aryl-3-substituted carbonyl pyridone compound
  • Use of aryl-3-substituted carbonyl pyridone compound
  • Use of aryl-3-substituted carbonyl pyridone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: Preparation of starting material A (3,4-dimethoxyacetophenone):

[0026] starting material A

[0027] Catechol (11.0 grams, 0.1 moles) was dissolved in 150 milliliters of acetone, potassium carbonate (27.6 grams, 0.20 moles) and dimethyl sulfate (12.6 grams, 0.1 moles) were added; reflux reaction for 10 hours, TLC showed After the reaction was complete, it was filtered, the filter cake was washed with ethyl acetate, and concentrated to obtain a crude oil product, which was subjected to short silica gel column chromatography to obtain o-dimethoxybenzene (12.1 g, yield 81%).

[0028] O-dimethoxybenzene (13.8 grams, 0.1 moles) was dissolved in 150 milliliters of dichloromethane, then anhydrous zinc chloride powder (26.8 grams, 0.20 moles) was added, and acetic anhydride (15.3 g, 0.15 moles); after the dropwise addition, the reaction was slowly raised to room temperature for 12 hours, then the reactant was carefully poured into 600 milliliters of ice water, e...

Embodiment 2

[0029] Example 2: Preparation of starting material B (2,5-dimethoxyacetophenone):

[0030] starting material B

[0031]In the same manner as in Example 1, using p-diphenol (11.0 g, 0.1 mol) as a raw material, the starting material B (2,5-dimethoxyacetophenone) was obtained as a colorless oil. H NMR spectrum 1 H-NMR (400MHz, deuterated chloroform, δppm) 2.62 (single peak, 3H, COCH 3 ), 3.77 (single peak, 3H, OCH 3 ), 3.79 (single peak, 3H, OCH 3 ), 6.89 (doublet, 1H, J=8.4Hz, H-4), 7.03 (doublet, 1H, J=8.4Hz, H-3), 7.30 (singlet, 1H, H-6).

Embodiment 3

[0032] Example 3: Preparation of intermediate compound IIIa [3-cyano-6-(3,4-dimethoxyphenyl)-2H-pyridin-2-one]:

[0033] Compound IIIa

[0034] Sodium metal (2.76 g, 120 mmol) was added to 250 ml of ether, 1 ml of ethanol was added dropwise, and starter A (3,4-dimethoxyacetophenone) (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 evaporated under reduced pressure, the solid mixture was added cyanoacetamide (12.6 grams, mol) and water (400 ml). After the mixture was refluxed for 8 hours, cooled, acidified with acetic acid, and filtered to obtain a yellow solid, after drying, the initial product was recrystallized from ethanol to obtain intermediate compound IIIa[3-cyano-6-(3,4-dimethoxy Phenyl)-2H-pyridin-2-one]: Yield: 56%, pale yellow solid; Melting point > 250°C; R f (Dichloromethane / methanol 20:1) 0.46; H NMR 1 H-N...

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Abstract

The invention provides aryl-3-substituted carbonyl-pyridinones and the application of medicine salts thereof to the preparation of anti-neoplastic drugs, and main relates to 6-aryl-3-substituted carbonyl-pyridinones and the medicine salts thereof. 6-aryl-3-substituted carbonyl-pyridinone derivatives provided by the invention have obvious growth inhibitory activity to promyelocytic leukemia cells cultured in vitro (HL-60) and mouse lymphoid tumor cell strains (P388D1); therefore, the 6-aryl-3-substituted carbonyl-pyridinone derivatives have the expectable purpose of being used as the drugs fortreating the correlative tumorous diseases of leukemia.

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-pyridone compounds for preparing antitumor drugs and pharmaceutical compositions. According to the pharmacological activity test, this type of compound has the activity of significantly inhibiting the growth of human myeloid leukemia cells (HL-60) and mouse lymphoid tumor cell lines (P388D1) cultured in vitro, and can be expected to be used as a therapeutic agent for the prevention and treatment of leukemia and related neoplastic diseases. drug use. Background technique [0002] Leukemia (leukemia), commonly known as blood cancer, is one of the top ten high-incidence malignant tumors in China. It is a malignant disease of the hematopoietic system. It is different from general cancers in that its pathogenic cause is still in the bone marrow or other hematopoietic cells in the hematopoieti...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/496A61K31/44A61K31/4545A61P35/00
Inventor 赵昱邹宏斌王晓雨阳应华张丽娟吴昊曾苏
Owner ZHEJIANG UNIV
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