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N-benzenesulfonyl-3-acetyl indole acyl hydrazone compound, preparation method and application

A technology of acetyl indolehydrazone and benzenesulfonyl, applied in the field of organic synthesis, to achieve the effect of reducing product loss

Inactive Publication Date: 2015-12-30
HENAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the research on the anti-HIV-1 activity of N-benzenesulfonyl-3-acetylindolehydrazone derivatives has not been reported yet.

Method used

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  • N-benzenesulfonyl-3-acetyl indole acyl hydrazone compound, preparation method and application
  • N-benzenesulfonyl-3-acetyl indole acyl hydrazone compound, preparation method and application
  • N-benzenesulfonyl-3-acetyl indole acyl hydrazone compound, preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] The preparation method of formula a-1 compound is:

[0048] 3mmol of AlCl 3 Add to a 50mL flask, add 5mL of dichloromethane, then add 1.5mmol of acetyl chloride at room temperature, react for 15min, add dropwise N-benzenesulfonyl indole dissolved in dichloromethane, react at room temperature for 2h, and detect by TLC After the reaction was complete, 10 mL of water was added to terminate the reaction, and extracted with dichloromethane (20 mL×3 times), the organic phases were combined, washed successively with saturated sodium bicarbonate solution (10 mL) and saturated sodium chloride solution (10 mL), and anhydrous sulfuric acid dried over sodium, concentrated under reduced pressure to obtain the crude product, and used GF 254 Thin layer chromatography Silica gel prepares a 20cm×20cm thin layer chromatography plate, dissolves the crude product in a small amount of dichloromethane and loads the sample on the thin layer chromatography plate, develops and separates to obt...

Embodiment 2

[0059] The preparation method of compound 2 is: take compound of formula a-1 (0.5mmol, prepared as above), m-chlorobenzohydrazide (0.5mmol) in 50mL flask, and add 5mL absolute ethanol to make it dissolve, add dropwise ( 1-2 drops) of glacial acetic acid and reflux reaction, after the reaction lasted for several minutes (5-10min), a large amount of solids began to be produced, and TLC tracked and detected that the reaction of the raw materials was complete; placed at room temperature to make it completely crystallized, and the crude product was obtained by suction filtration under reduced pressure. The product was washed several times with refrigerated (-20°C) absolute ethanol to obtain pure compound 2.

[0060] The reaction formula for preparing compound 2 by formula a-1 compound is as follows:

[0061]

[0062] The physicochemical properties of compound 2 are as follows:

[0063] 1), white solid, melting point 196-198°C, yield 87%.

[0064] 2), the nuclear magnetic reson...

Embodiment 3

[0068] The preparation method of formula a-2 compound is:

[0069] 3mmol of AlCl 3 Add to a 50mL flask, add 5mL of dichloromethane, then add 1.5mmol of acetyl chloride at room temperature, react for 15min, add dropwise N-nitrobenzenesulfonylindole dissolved in dichloromethane, and react for 2h at room temperature 10mL of water was added to stop the reaction after TLC detection was complete, and extracted with dichloromethane (20mL×3 times), the organic phases were combined, and washed successively with saturated sodium bicarbonate solution (10mL) and saturated sodium chloride solution (10mL), Dry over anhydrous sodium sulfate, concentrate under reduced pressure to obtain crude product, use GF 254 Thin-layer chromatography Silica gel prepared a thin-layer chromatography plate of 20 cm × 20 cm, and the crude product was dissolved in a small amount of dichloromethane and then loaded on the thin-layer chromatography plate, developed and separated to obtain the compound of formula...

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Abstract

The invention discloses an N-benzenesulfonyl-3-acetyl indole acyl hydrazone compound, a preparation method and application and belongs to the technical field of organic synthesis. An N-benzenesulfonyl-3-acetyl indole acyl hydrazone derivative uses benzpyrole or 6-methylindole as a raw material, benzenesulfonyl is introduced to the nitrogen position in the first place, an N-benzenesulfonyl-3-acetyl indole derivative is obtained through acetylation at the C-3 position, the N-benzenesulfonyl-3-acetyl indole derivative further conducts a reaction with hydrazide, the corresponding N-benzenesulfonyl-3-acetyl indole acyl hydrazone derivative is obtained, the preparation technology is simple, operation is simple and convenient, and the N-benzenesulfonyl-3-acetyl indole acyl hydrazone compound and the preparation method and application are suitable for large-scale production and application. The N-benzenesulfonyl-3-acetyl indole acyl hydrazone derivative has remarkable anti-HIV-1 activity, part of compound is safe to normal cells of human bodies under high concentration and has significant activity of normal cell lesion inhibition caused by HIV-1 virus under low concentration, and the N-benzenesulfonyl-3-acetyl indole acyl hydrazone compound can be used for preparing novel anti-HIV-1 drugs.

Description

technical field [0001] The present invention relates to a kind of N-benzenesulfonyl-3-acetylindolehydrazone compound, and also relates to the preparation method and application of N-benzenesulfonyl-3-acetylindolehydrazone compound, belonging to organic synthesis technology field. Background technique [0002] In recent years, with the interpenetration of disciplines and the rapid development of enzymology and immunovirology, people have become more and more thorough in the research on the structure of HIV itself and the various links of infecting the host, which is more conducive to targeted research and development Anti-HIV drug with high efficiency and low toxicity. Using the principle of union to gather various active groups in the same molecule in order to find better drugs is a hot research topic in today's society. As we all know, aroylhydrazone compounds containing [-CONHN=CH-] groups have strong coordination ability and special biological activity, and are inhibito...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/14C07D409/12C07D401/12A61P31/18
CPCC07D209/14C07D401/12C07D409/12
Inventor 车志平田月娥陈应武刘圣明胡镇杰
Owner HENAN UNIV OF SCI & TECH
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