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Piperazine derivant with antineoplastic activity

A kind of derivative, the technology of piperazine, applied in the field of piperazine derivatives

Inactive Publication Date: 2012-07-11
TIANJIN POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are few studies on this type of compound, and there are no reports on N, N-disubstituted piperazine compounds.

Method used

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  • Piperazine derivant with antineoplastic activity
  • Piperazine derivant with antineoplastic activity
  • Piperazine derivant with antineoplastic activity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Prepare the chlorinated carvone intermediate by the existing mature method: dissolve 15.0 g (0.1 mol) of carvone in 300 mL of n-hexane, place in an ice bath at 0-5°C, and add 13.3 tert-butyl hypochlorite dropwise under stirring. g (0.11mol), the addition was completed and raised to room temperature, and continued to stir for 3h. The reaction solution was washed successively with saturated aqueous sodium sulfite solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated to obtain 10.7 g of a yellow oil with a yield of 72.7%. 1 H NMRδ(ppm): 1.76(s, 3H), 2.33-2.40(m, 2H), 2.49-2.66(m, 2H), 2.94(m, 1H), 4.06(s, 2H), 5.03(s, 1H ), 5.23(s, 1H), 6.73(m, 1H).

Embodiment 2

[0018] Synthesis of N,N-bis[2-(4-methyl-5-oxocyclohex-3-ene)allyl]piperazine hydrochloride (1)

[0019] Dissolve 16.2mmol of chlorocarvone intermediate, 8.9mmol of potassium carbonate, and 8.1mmol of piperazine in 15mL of ethanol, and heat to reflux for 8h. Ethanol was evaporated, the residue was dissolved in 30mL dichloromethane, washed with 1N hydrochloric acid solution (30mL×3), the acid solution was combined, neutralized with anhydrous sodium carbonate to pH9.0~10.0, extracted with dichloromethane (30mL×5 ), the organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a yellow oil, which was dissolved in hydrochloric acid ethanol and allowed to stand for crystallization to obtain a white crystalline solid. Product yield: 67.9%, mp: 195-197°C. 1 H-NMRδ(ppm): 1.77(s, 6H), 2.20-2.67(m, 16H), 2.85(m, 2H), 2.92(s, 4H), 4.92(s, 2H), 5.01(s, 2H) , 6.74 (m, 2H); MS (EI) m / z: 382 (M + , 100)...

Embodiment 3

[0021] Synthesis of 2-methyl-N,N-bis[2-(4-methyl-5-oxocyclohex-3-ene)allyl]piperazine hydrochloride (2)

[0022] Reaction process is with embodiment 2. Product yield: 77.4%, mp: 190-192°C. 1 H NMRδ(ppm): 1.24(m, 3H), 1.79(s, 6H), 2.30-2.49(m, 15H), 2.84(m, 2H), 2.92(s, 4H), 4.91(s, 2H), 5.02(s, 2H), 6.75(m, 2H); MS(EI) m / z: 410(M + , 5), 192(100).

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Abstract

The invention discloses piperazine derivatives with anti-tumor activity, which have a structure as right, in the formula, when X is C=O, R is H or -CH3; and when X is -CHOH or -CH2, R is H. The compounds are obtained by using carvone as an initial raw material through chlorination reaction, condensation reaction, sodium borohydride reduction and Huang Min-lon reduction reaction. In vitro experiments show that the compounds have stronger propagation inhibiting effect on a cancer cell strain Lncap of human pancreas, are potential anti-tumor medicaments, and have application to preparing anti-tumor pharmaceutical preparations.

Description

technical field [0001] The present invention relates to a class of piperazine derivatives with anti-tumor effect, specifically a kind of 2,5-disubstituted-N,N-bis[2-(4-methyl-5 substituted cyclohex-3-ene)ene Propyl]piperazine, this type of compound has the characteristics of good water solubility and high antitumor activity, is a potential antitumor drug, and has the purpose of preparing antitumor drug preparations. Background technique [0002] Cancer is a serious threat to human life and health, and is one of the diseases with the highest mortality rate. Although dozens of effective anticancer drugs have entered clinical practice and achieved good results in the treatment of malignant tumors, the treatment of solid tumors, which account for more than 90% of malignant tumors, has not yet achieved satisfactory results. Therefore, research on anticancer drugs is still one of the important tasks in the field of medicine. [0003] Nitrogen-containing heterocycles exist in man...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D295/03C07D295/096C07D295/112A61K31/495A61P35/00
Inventor 陈娇娇陈莉赵义平傅宏俊
Owner TIANJIN POLYTECHNIC UNIV