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Novel piperazine and homopiperazine derivative and preparation method and use thereof

A technology of homopiperazine and piperazine, which is applied in drug combination, nervous system diseases, organic chemistry, etc., and can solve the problems of limited clinical application and poor water solubility

Inactive Publication Date: 2014-04-02
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of these drugs have poor water solubility, which limits their clinical application as oral and injectable agents

Method used

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  • Novel piperazine and homopiperazine derivative and preparation method and use thereof
  • Novel piperazine and homopiperazine derivative and preparation method and use thereof
  • Novel piperazine and homopiperazine derivative and preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0109] Example 1: Preparation of 1-methyl-4-(10-acetoxy-2-decenoyl)piperazine (compound 1)

[0110] Step 1: the preparation of 10-acetoxy-2-decenoic acid

[0111]

[0112] Under stirring conditions, 10-hydroxy-2-decenoic acid (9.30g, 50mmol) and acetic anhydride (9.43mL, 100mmol) were successively added to a 50mL dry round bottom flask, and the above mixture was placed in a 100°C oil bath Heat to reflux for 1h. The reaction solution was concentrated under reduced pressure, and the crude product obtained was subjected to silica gel column chromatography (eluent: V 丙酮 :V 石油醚 =1:20) separation and purification to obtain 9.51g light yellow oily liquid, productive rate 83.4%.

[0113] Step 2: Preparation of 1-methyl-4-(10-acetoxy-2-decenoyl)piperazine (compound 1)

[0114]

[0115] 10-Acetoxy-2-decenoic acid (2.28g, 10mmol), dichloromethane (30mL) were added to a 50mL round bottom flask, and SOCl was added dropwise under stirring 2 (1.46mL, 20mmol), stirred at room tempe...

Embodiment 2

[0116] Example 2: Preparation of 1-ethyl-4-(10-acetoxy-2-decenoyl)piperazine (compound 2)

[0117]

[0118] The method is the same as that of the intermediate example 1, and ethylpiperazine is substituted for methylpiperazine to obtain 5.56 g of light yellow oily liquid with a yield of 85.8%. 1H NMR (CD 3 OD,500MHz)δ:6.86~6.70(m,1H,CH=CHCO),6.45(d,J=14.9Hz,1H,CH=CHCO),4.07(t,J=6.7Hz,2H,OCH 2 –(CH 2 ) 5 –CH 2 ),3.68(t,J=5.0Hz,4H,(CH 2 ) 2 NC 2 h 5 ),2.55~2.45(m,6H,CON(CH 2 ) 2 and NCH 2 CH 3 ),2.30~2.24(m,2H,OCH 2 –(CH 2 ) 5 –CH 2 ),2.05(s,3H,CH 3 CO 2 ),1.68~1.35(m,10H,OCH 2 –(CH 2 ) 5 –CH 2 ),1.14(t,J=7.2Hz,3H,NCH 2 CH 3 ); 13 CNMR (CD 3 OD,125MHz)δ:171.6,166.3,146.8,119.9,64.3,52.7,52.1,51.8,45.2,41.5,32.1,28.8,28.7,28.6,28.3,25.6,19.7,10.7; ESI-MS m / z:325.23 (M+1) + ;IR(KBr,cm –1 )ν: 1738(C=O), 1659(C=O), 1622(C=C), 1243(C–O–C).

Embodiment 3

[0119] Example 3: Preparation of 1-hexyl-4-(10-acetoxy-2-decenoyl)piperazine (compound 3)

[0120]

[0121] Method is with intermediate embodiment 1, and hexylpiperazine is replaced methylpiperazine, and the thick product of gained is with silica gel column chromatography (eluent: V 甲醇 :V 乙酸乙酯 =1:2) separation and purification to obtain 5.92 g of a light yellow oily liquid, with a yield of 77.8%. 1 H NMR (DMSO-d 6 ,500MHz)δ:6.69~6.10(m,1H,CH=CHCO),6.44(d,J=15.0Hz,1H,CH=CHCO),4.06(t,J=6.6Hz,2H,OCH 2 –(CH 2 ) 5 –CH 2 ),3.55~3.45(m,4H,(CH 2 ) 2 N(CH 2 ) 5 CH 3 ),2.35~2.23(m,6H,CON(CH 2 ) 2 and NCH 2 –(CH 2 ) 4 –CH 3 ),2.21~2.14(m,2H,OCH 2 –(CH 2 ) 5 –CH 2 ),2.00(s,3H,CH 3 CO 2 ),1.60~1.22(m,18H,OCH 2 –(CH 2 ) 5 –CH 2 and NCH 2 –(CH 2 ) 4 –CH 3 ),0.87(t,J=6.5Hz,3H,NCH 2 –(CH 2 ) 4 –CH 3 ); 13 C NMR (DMSO-d 6 ,125MHz)δ:170.8,164.8,145.6,121.1,64.2,64.1,58.2,53.7,53.0,45.5,32.0,31.7,30.4,28.9,28.8,28.6,28.3,27.8,27.0,26.6,25.8,22.5,21.2 ,14.3;...

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Abstract

The invention relates to a compound of formula I or pharmaceutically acceptable salt and a preparation method thereof, as well as a drug composition containing the same. The compound of formula I is novel piperazine and homopiperazine derivative, which can be used for preparing cervical cancer-treating medicine, anti-acetylcholinesterase and butyrylcholinesterase medicine, and medicine for treating staphylococcus aureus infection.

Description

technical field [0001] The present invention relates to novel piperazine and homopiperazine derivatives, or pharmaceutically acceptable salts and solvates thereof, a preparation method thereof, and a pharmaceutical composition containing the above substances. Background technique [0002] Piperazine, also known as hexahydropyrazine, is a six-membered heterocyclic ring containing two nitrogen atoms in the molecule. It has high formation enthalpy and good thermal stability. It is an ideal structural unit of nitrogen-rich heterocyclic compounds and an important component of many drugs. part. Compared with traditional organic drugs, piperazine compounds have a better nitrogen balance symmetrical structure. The introduction of piperazine ring in organic synthesis as a synergistic group of drugs can improve the pharmacokinetic properties of drugs and increase the biological activity of drugs. [0003] Different substituents are introduced on the piperazine ring. Due to the diffe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D295/185A61K31/551A61K31/495A61P35/00A61P35/02A61P25/28A61P31/02A61P31/04
Inventor 苏桂发郑志兵农娟李松王莉莉覃江克潘成学唐煌邓业成
Owner GUANGXI NORMAL UNIV
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