Synthesis and uses of serial ion liquid as candidate drug with anticancer activity

Abstract

The invention discloses an artificial synthetic new-typed anti-cancer drug with a series of ion liquid structure, whose structural formula is displayed in the formula (I), wherein R1,R2, R3,R4,R5,R6,X are defined as instruction; the compound inhibits tumour cell strongly such as Hela299,B16,SMMC-7721 and so on in the external anticancer activity test with effective density less than 10 mug / ml.

Description

technical field

[0001] The present invention relates to a class of anticancer medicine with ionic liquid structure and its application in preparing medicine for treating cancer. technical background

[0002] Cancer is one of the most harmful diseases to human health and life. The development of anticancer drugs has always been a hot topic for scientists. Due to the complexity and particularity of the pathogenesis of cancer, the search for anticancer drugs with high selectivity, high efficiency, and less toxic and side effects has not achieved ideal results.

[0003] An ionic liquid is a molten salt system composed of a large cation and anion that is liquid at or near room temperature. Ionic liquids have many unique physical and chemical properties, such as a wide range of liquid states, no vapor pressure, odorless, non-toxic, non-flammable, recyclable, etc., so it is considered as a potential green solvent and has attracted academic attention. The world and the business c...

Examples

Embodiment 1

[0124] Example 1: Synthesis of 1,2,3,4-tetramethyl-5,6-dihexylguanidine bromide ionic liquid: (compound 1) tetramethylguanidine 10mmol, potassium carbonate 20-30mmol, n-bromohexyl Dissolve 20-30mmol of alkane in 20-100mL of acetonitrile and reflux for 10-30h. The reaction mixture was cooled, 50-100 mL of water, 50-100 mL of 25-35% (Wt%) NaOH solution were added, and petroleum ether (15-30 mL×3) was added to extract unreacted alkyl halides. The petroleum ether was back-extracted with water, the aqueous solutions were combined, and 10-30 mL of a saturated aqueous solution of sodium bromide was added. use CH 2 Cl 2 (25mL×3) extract the above aqueous solution, combine the organic phases, and use anhydrous Na 2 SO 4 dry. The solvent was removed by rotary evaporation to obtain the crude product. The crude product was recrystallized from ethyl acetate / acetonitrile to obtain the target product.

Embodiment 2

[0125] Example 2: Synthesis of 1,2,3,4-tetramethyl-5,6-diheptylguanidine bromide ionic liquid: (compound 2)

[0126] Adopt the synthetic method of example 1 to carry out, and starting material adopts n-bromoheptane to replace n-bromohexane.

Embodiment 3

[0127] Example 3: Synthesis of 1,2,3,4-tetramethyl-5,6-dioctylguanidine bromide ionic liquid: (compound 3)

[0128] Adopt the synthetic method of example 1 to carry out, and starting material adopts n-bromooctane to replace n-bromohexane.

technical field

[0001] The present invention relates to a class of anticancer medicine with ionic liquid structure and its application in preparing medicine for treating cancer. technical background

[0002] Cancer is one of the most harmful diseases to human health and life. The development of anticancer drugs has always been a hot topic for scientists. Due to the complexity and particularity of the pathogenesis of cancer, the search for anticancer drugs with high selectivity, high efficiency, and less toxic and side effects has not achieved ideal results.

[0003] An ionic liquid is a molten salt system composed of a large cation and anion that is liquid at or near room temperature. Ionic liquids have many unique physical and chemical properties, such as a wide range of liquid states, no vapor pressure, odorless, non-toxic, non-flammable, recyclable, etc., so it is considered as a potential green solvent and has attracted academic attention. The world and the business c...

Examples

Embodiment 1

[0124] Example 1: Synthesis of 1,2,3,4-tetramethyl-5,6-dihexylguanidine bromide ionic liquid: (compound 1) tetramethylguanidine 10mmol, potassium carbonate 20-30mmol, n-bromohexyl Dissolve 20-30mmol of alkane in 20-100mL of acetonitrile and reflux for 10-30h. The reaction mixture was cooled, 50-100 mL of water, 50-100 mL of 25-35% (Wt%) NaOH solution were added, and petroleum ether (15-30 mL×3) was added to extract unreacted alkyl halides. The petroleum ether was back-extracted with water, the aqueous solutions were combined, and 10-30 mL of a saturated aqueous solution of sodium bromide was added. use CH 2 Cl 2 (25mL×3) extract the above aqueous solution, combine the organic phases, and use anhydrous Na 2 SO 4 dry. The solvent was removed by rotary evaporation to obtain the crude product. The crude product was recrystallized from ethyl acetate / acetonitrile to obtain the target product.

Embodiment 2

[0125] Example 2: Synthesis of 1,2,3,4-tetramethyl-5,6-diheptylguanidine bromide ionic liquid: (compound 2)

[0126] Adopt the synthetic method of example 1 to carry out, and starting material adopts n-bromoheptane to replace n-bromohexane.

Embodiment 3

[0127] Example 3: Synthesis of 1,2,3,4-tetramethyl-5,6-dioctylguanidine bromide ionic liquid: (compound 3)

[0128] Adopt the synthetic method of example 1 to carry out, and starting material adopts n-bromooctane to replace n-bromohexane.

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