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Application of cyano-containing diphenylamine compound to preparation of antitumor drugs

A technology containing cyanodiphenylamine and anti-tumor drugs, which is applied in the field of anti-tumor drugs and medicine, and can solve the problems of no reports of anti-tumor drugs in compounds

Active Publication Date: 2015-07-15
中国中化股份有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In the prior art, the compounds whose structures are shown in the general formula I of the present invention have not been reported as antitumor drugs

Method used

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  • Application of cyano-containing diphenylamine compound to preparation of antitumor drugs
  • Application of cyano-containing diphenylamine compound to preparation of antitumor drugs
  • Application of cyano-containing diphenylamine compound to preparation of antitumor drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0123] Embodiment 1: the preparation of table 6-1 compound

[0124]

[0125]Add 0.30 g (7.52 mmol) of sodium hydroxide to 0.35 g (3.76 mmol) of aniline in 40 ml of N,N-dimethylformamide, and slowly add 2,4,5,6-tetrachloro-1 , 3-phthalonitrile 1.00g (3.76mmol), after adding, continue to stir at room temperature for 5h, after TLC monitors the reaction, the reaction solution is poured into water, white solid is precipitated, suction filtration, and the filter cake is washed with 30ml water for two Once, washed twice with 20ml of petroleum ether, and dried to obtain 1.65g of the product, which is the compound in Table 6-1. Off-white solid, melting point 226-228°C.

[0126] 1 H-NMR (300MHz, internal standard TMS, solvent CDCl 3 ) δ (ppm): 7.22 (d, 2H, Ph-2, 6-2H, J = 7.5 Hz), 7.40-7.46 (m, 3H, Ph-3, 4, 5-3H).

Embodiment 2

[0127] Embodiment 2: the preparation of table 6-33 compound

[0128]

[0129] To a solution of 1.03g (8mmol) 2,6-difluoroaniline in 40ml N,N-dimethylformamide, add 0.64g (16mmol) of sodium hydroxide, and slowly add 2,4,5,6- Tetrachloro-1,3-benzenedicarbonitrile 2.13g (8mmol), after adding, continue stirring at room temperature for 5h, after TLC monitors the reaction, pour the reaction solution into water, extract with ethyl acetate, and wash the organic phase with water successively. Wash with saturated brine, dry, filter, precipitate, and purify the residue by column chromatography (eluent is ethyl acetate and petroleum ether (boiling range 60-90°C), volume ratio is 1:4) to obtain 1.65 g of the product, namely Table 6-33 Compounds. Pale yellow solid, melting point 264-266°C.

[0130] 1 H-NMR (300MHz, internal standard TMS, solvent CDCl 3 ) δ (ppm): 6.70 (s, 1H, NH), 7.07 (t, 2H, Ph-3, 5-2H, J = 8.1 Hz), 7.37 (m, 1H, Ph-4-1H).

Embodiment 3

[0131] Embodiment 3: the preparation of table 6-39 compound

[0132]

[0133] The synthesis method is the same as that of the compound in Table 6-1, a brownish black solid with a melting point of 209-212°C.

[0134] 1 H-NMR (300MHz, internal standard TMS, solvent CDCl 3 )δ (ppm): 6.95 (s, 1H, NH), 7.20 (d, 1H, Ph-6-H, J=8.1Hz), 7.36 (dd, 1H, Ph-5-H, 3 J=8.7Hz, 4 J = 2.7 Hz), 7.54 (d, 1H, Ph-3-H, J = 2.4 Hz).

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Abstract

The invention discloses application of a cyano-containing diphenylamine compound shown in a general formula I in the specification to preparation of antitumor drugs. The definition of each substituent group in the formula refers to the specification. The compound in the general formula I has good antitumor activity and especially has excellent activities on human lung cancer A549, human leukemia HL-60 and the like.

Description

technical field [0001] The invention belongs to the field of medicine and relates to the field of antitumor drugs. Specifically, it relates to the application of a cyano-diphenylamine-containing compound as an antitumor drug. Background technique [0002] Patent CN101391981A discloses that the compound shown in the following general formula can be used as an intermediate for synthesizing a new polyhalogenated acridone compound with fluorescence activity and potential drug activity, wherein compound KC1 (compound code IV-A ), KC2 (compound code IV-B), KC3 (compound code IV-D), KC4 (compound code IV-E), KC5 (compound code IV-H), KC6 (compound code IV-C), but without any Biological activity report; literature Pesticide Science (1988), 24 (2), 111-21 reported that compound KC1 (wherein code-named XXIX) has certain activity to related diseases such as grape downy mildew (Plasmopora viticola) etc. under high dosage . [0003] [0004] The applicant applied for the compound r...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/277A61K31/44A61P35/00
Inventor 刘长令柴宝山李慧超关爱莹
Owner 中国中化股份有限公司