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Heteraromatic ring thiosemicarbazone compound, and its derivatives and their use forpreparing antitumour medicine

A technology of thiosemicarbazone and compound, which can be used in antitumor drugs, drug combination, organic chemistry and other directions, and can solve problems such as no antitumor activity.

Inactive Publication Date: 2007-01-10
卡南吉医药科技(上海)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In addition to the above-mentioned uses of heterocyclic aryl thiosemicarbazone compounds and their derivatives, there has been no report of anti-tumor activity

Method used

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  • Heteraromatic ring thiosemicarbazone compound, and its derivatives and their use forpreparing antitumour medicine
  • Heteraromatic ring thiosemicarbazone compound, and its derivatives and their use forpreparing antitumour medicine
  • Heteraromatic ring thiosemicarbazone compound, and its derivatives and their use forpreparing antitumour medicine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0097] The synthesis of embodiment 1 2-pyridyl-benzophenone

[0098] A solution of 2-cyanopyridine (104 g, 1 mol) in THF (200 mL) was added dropwise into freshly prepared phenyl Grignard reagent (1.5 L ether-THF solution, 1 mol) at room temperature, and the mixture was stirred overnight. 20% aqueous ammonium chloride (600 mL) was added and stirred for 2 hours, then extracted with ethyl acetate (3 x 500 mL). The extract was dried with anhydrous sodium sulfate, filtered and concentrated to dryness to obtain the product which could be directly used in the next step (Example 4).

Embodiment 2

[0099] Example 2 Synthesis of 2-pyridyl-2-thienyl ketone

[0100] As in Example 1, the newly prepared 2-thienyl Grignard reagent (prepared from 2-bromothiophene by a conventional method) was reacted with 2-cyanopyridine to obtain the product (directly used in Example 5).

Embodiment 3

[0101] Embodiment 3 N, the synthesis of N-dimethyl-N'-thiosemicarbazide

[0102] Carbon disulfide (3.8 g, 50 mmol) was added dropwise to an aqueous solution (50 mL) of sodium hydroxide (2.4 g, 60 mmol) and dimethylamine (5.45 g, 33% in water, 40 mmol) at room temperature middle. After the reaction was stirred for 2 hours, aqueous sodium chloroacetate (5.8 g, 50 mmol) (30 mL) was added dropwise and stirring was continued for 20 hours. The reactant was acidified with dilute HCl solution to pH = 3, and the precipitate was filtered to obtain 4.2 g of the intermediate. The intermediate was mixed with sodium hydroxide (0.9 g, 20 mmol), hydrazine hydrate (2 ml, 85%) and water (12 ml), heated to reflux for 4 hours, and a solid precipitated after cooling. After filtration, the solid was dissolved in hot dichloromethane, and the filter residue was removed by filtration. The filtrate was concentrated to obtain the crude product, which was recrystallized in ethanol to obtain 0.8 g of th...

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Abstract

The invention discloses thiosemicarbazon compounds, their derivatives and their applications for the preparing of antineoplastic drugs. The compound of the invention shows its good inhibitory effect on tumor through the experiments on animals. For example, the inhibition effect on the solid tumor S180 on mouse is up to 81.1%. The compounds can be made into tablet, capsule or injection agent in many forms.

Description

technical field [0001] The present invention relates to thiosemicarbazone compounds and their derivatives and uses, in particular to a heteroaromatic ring thiosemicarbazone compound and its derivatives and their application in the preparation of antitumor drugs. Background technique [0002] Thiosemicarbazone compounds have various biological activities. It has been used in antibacterial agents (Foye, W.O.; Banijamali, A.R.; Patarapanich, C.J.Pharm.Sci.1986, 75, 1180; Easmon, J.), antimalarial agents (Klayman, D.L.; Scovill, J.P.; Bartosevich, J.F.; Mason, C.J., J.Med.Chem.1979, 22, 1367), antiviral agents (Heinisch, G.; Holzer, W.; Rosenwirth, B.; Arzneim.-Forsch.1989, 39, 1196), inhibitors of dihydrofolate reductase (Foye, W.O.; Dabade, S.V.; Kelley, C.J.; Lebrun, E.; Rapenbusch, R.Med.Chem.Res.1998, 8, 542), neurotrophic Chelating agent (Lukevics et al, Eur.J.Med.Chem.1995,30,983), it and metal ions can be used in the treatment of diseases related to cell proliferation ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/22C07D213/53C07D239/26C07D241/12C07D409/06C07D401/06C07D413/06C07D417/06A61K31/381A61K31/4436A61K31/506A61K31/497A61P35/00
Inventor 王晓川齐铭
Owner 卡南吉医药科技(上海)有限公司
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