Acetamide derivative and application thereof in pharmacy

A technology of acetamide and derivatives, applied in the field of medicine, can solve the problems of listing, no drugs, and cancer cells initiating programmed death.

Active Publication Date: 2010-05-26
JIANGSU CAREFREE PHARM CO LTD
View PDF0 Cites 14 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, there are studies at home and abroad on caspase-3 causing cancer cells to ini

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Acetamide derivative and application thereof in pharmacy
  • Acetamide derivative and application thereof in pharmacy
  • Acetamide derivative and application thereof in pharmacy

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1.2-(4-benzyl-2-piperazinon-1-yl)-N-[(2-hydroxyl-3-allyl-phenyl)methyleneamino]acetamide (I 1 ) preparation and structure confirmation

[0037] (1). Synthesis of 4-benzyl-2-piperazinone

[0038] Add 5.1g of 2-piperazinone, 5.0g of benzyl chloride and 4.2g of sodium bicarbonate into 60ml of ethanol respectively, stir, heat to reflux for 5h, cool to room temperature, filter, concentrate the filtrate to obtain a solid, recrystallize from benzene to obtain 8.6g of white crystals (melting point 152-154°C).

[0039] (2). Synthesis of 2-(4-benzyl-2-piperazinon-1-yl)-ethyl acetate

[0040] Add 8.55g of 4-benzyl-2-piperazinone and an appropriate amount of sodium hydride into dry 100mL of acetone, stir, add 6.2g of ethyl bromoacetate dropwise, start heating and refluxing until the reaction of the raw materials is complete, cool, filter, After washing, the filtrate was concentrated to obtain an oil, and column chromatography (eluent: ethyl acetate / n-hexane=4 / 1) obtained...

Embodiment 2

[0047] Example 2.2-[4-(3-pyridyl-methyl)-2-piperazinon-1-yl]-N-[(2-hydroxyl-3-allyl-phenyl)methyleneamino ] Acetamide (I 2 ) preparation and structure confirmation

[0048] (1). Synthesis of 4-(3-pyridyl-methyl)-2-piperazinone

[0049] Add 5.1g 2-piperazinone, 5.0g 3-chloromethylpyridine and 4.2g sodium bicarbonate into 60ml of ethanol respectively, stir, heat to reflux for 5h, cool to room temperature, filter, concentrate the filtrate, column chromatography (eluent : chloroform / methanol=10 / 1), collect eluent, concentrate to obtain product.

[0050] The resulting product obtains the target product in the same manner as (2), (3), and (4) in Example 1.

[0051] 1 H-NMR (DMSO, -d 6 )δ8.75(s, 1H), 8.6(s, 1H), 8.15(s, 1H), 7.95(s, 1H), 7.8(s, 1H), 7.5(s, 1H), 7.2(s, 1H ), 6.8(s, H), 6.65(s, H), 6.25(s, H), 5.16(s, 1H), 4.91(ddd, 2H), 4.12(dd, 2H), 3.66(dd, 2H) , 3.37(s, 2H), 3.24(d, 2H), 3.16(d, 2H), 2.64(d, 2H).

[0052]

Embodiment 3

[0053] Example 3.2-(4-p-toluenesulfonyl-2-piperazinonyl-1-yl)-N-[(2-hydroxyl-3-allyl-phenyl)methyleneamino]acetamide (I 3 ) preparation and structure confirmation

[0054] (1). Synthesis of 4-p-toluenesulfonyl-2-piperazinone

[0055] Add 5.1g of 2-piperazinone, 7.6g of p-toluenesulfonyl chloride and 5.1g of triethylamine into 60ml of dichloromethane respectively, stir, heat to reflux for 5h until the reaction is complete, cool to room temperature, filter, concentrate the filtrate, and perform column chromatography (Eluent: chloroform / methanol=10 / 1), collect the eluent, and concentrate to obtain the product.

[0056] The resulting product obtains the target product in the same manner as (2), (3), and (4) in Example 1.

[0057] 1 H-NMR (DMSO-d 6 )δ8.15(s, 1H), 7.90(s, 1H), 7.81(s, 2H), 7.35(s, 1H), 7.23(s, 2H), 6.9(s, H), 6.63(s, H ), 6.2(s, H), 5.10(s, 1H), 4.91(ddd, 2H), 4.2(dd, 2H), 3.38(s, 2H), 3.28(d, 2H), 3.16(d, 2H) , 2.60(d, 2H), 2.32(d, 3H).

[0058]

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention provides an acetamide derivative with the structural formula as follows: R represents -X-Ar, -X-COOH, -CO-Ar, -SO2-Ar, -X-Het., or -X-NR1R2, wherein X represents alkylene with 1-8 carbon atoms and the alkylene is not substituted or is substituted by straight chain hydrocarbon or branched hydrocarbon with 1-5 carbon atoms; and Ar represents phenyl, pyridyl, naphthyl, pyrimidyl and quinolyl. The derivative can cause apoptosis by acting on Caspase-3 zymogen in cancer cells and can be widely applied in cancer treatment.

Description

technical field [0001] The present invention relates to a compound derivative and its preparation method, and its application in pharmacy, in particular to an acetamide derivative, its preparation method, and its application in pharmacy, belonging to the technical field of medicine. Background technique [0002] Apoptosis and cell proliferation are the basic phenomena of life and the basic measures to maintain the dynamic balance of the number of cells in the body. During the embryonic development stage, excess cells and cells that have completed their missions are removed through apoptosis, ensuring the normal development of the embryo; aging and diseased cells are removed through apoptosis during the adult stage, ensuring the health of the body. Like cell proliferation, apoptosis is a precise process regulated by genes. There are two main pathways of cell apoptosis, one is to activate intracellular apoptotic enzyme caspase (caspase) through extracellular signal, and the o...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
IPC IPC(8): C07D241/08C07D241/06C07D405/04A61K31/495A61K31/496A61P35/00
Inventor 秦引林刘现军
Owner JIANGSU CAREFREE PHARM CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap