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Alkynyl thiophene ketone compound and preparation method and applications thereof

A technology of alkynyl thiophenone and compound, applied in the field of chemistry, can solve problems such as high synthesis cost and few types

Inactive Publication Date: 2009-10-28
SOUTH CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to overcome the shortcomings of the existing thiophene photoactivated drugs, such as fewer types and high synthesis costs, and provide a kind of alkynyl thiophenone compound with simple structure

Method used

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  • Alkynyl thiophene ketone compound and preparation method and applications thereof
  • Alkynyl thiophene ketone compound and preparation method and applications thereof
  • Alkynyl thiophene ketone compound and preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0126] Example 1: Preparation of 2-phenyl-1-(5-(2-phenylethynyl)thiophen-2-yl)ethanone

[0127] Weigh 18.4g (0.1mol) of 2-(2-phenylethynyl)thiophene and add it to 50ml of dichloromethane, add 2g of phosphoric acid as a catalyst, and add 15.4g of 2-phenylacetyl chloride to 50ml of dichloromethane dropwise at room temperature solution, stirring while dripping. After the dropwise addition was completed, the stirring reaction was continued for 2 hours, and the thin layer indicated the end point of the reaction. The product (compound 1) was obtained by water washing, extraction, solvent removal, and ethanol recrystallization according to routine laboratory methods.

Embodiment 2

[0128] Example 2: Preparation of 2-(naphthalene-2-yl)-1-(5-(2-phenylethynyl)thiophen-2-yl)ethanone

[0129] Weigh 18.4g (0.1mol) of 2-(2-phenylethynyl)thiophene and add it to 50ml of dichloromethane, add 2g of phosphoric acid as a catalyst, and add 20.4g of 2-(naphthyl-2-yl)ethane dropwise at room temperature Acyl chloride in 50ml of dichloromethane solution, stirring while dropping. Continue to stir the reaction after the dropwise addition, and the thin layer indicates the end point of the reaction. The product (compound 2) was obtained by washing with water, extracting, removing the solvent, and recrystallizing with ethanol according to routine laboratory methods.

Embodiment 3

[0130] Example 3: Preparation of 2-(thiophen-2-yl)-1-(5-(2-(thiophen-2-yl)ethynyl)thiophen-2-yl)ethanone

[0131] Weigh 18.9g (0.1mol) of 2-(2-(thiophen-2-yl)ethynyl)thiophene and add it to 50ml of dichloromethane, add 2g of phosphoric acid as a catalyst, and add 15.9g of 2-(thiophene-2 -base) 50ml dichloromethane solution of acetyl chloride, stirring while dropping. Continue to stir the reaction after the dropwise addition, and the thin layer indicates the end point of the reaction. The product (compound 4) was obtained by washing with water, extracting, removing the solvent, and recrystallizing with ethanol according to routine laboratory methods.

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Abstract

The invention discloses an alkynyl thienone ketone compound, and a preparation method and applications thereof. The alkynyl thienone ketone compound contains a structure shown as a general formula (I): in an inert solvent and under the action of catalyst, substituted 2-aromatic acetylenyl thiophene and substituted aromatic acetyl chloride are reacted to prepare the alkynyl thienone ketone compound. The alkynyl thienone ketone compound has toxicity or lower toxicity in self, can generate free radical for killing the toxicity under the action of light and oxygen, attack more biomacromolecules in an organism and by a free radical chain reaction and shows high efficiency; the compound exerts toxic effect and simultaneously also occurs the degradation and avoids the persistent residues in the environment, thereby further improving the security; the compound has insecticidal activity, weeding activity and the activities to microbes, such as epiphyte, bacteria, virus, and the like and has simple and portable preparation method as well as lower cost.

Description

technical field [0001] The invention belongs to the technical field of chemistry, and in particular relates to an alkynyl thiophenone compound and a preparation method and application thereof. Background technique [0002] Photoactivated drugs have no activity or very low activity on the target body under the condition of no light, but after receiving light (especially near ultraviolet light), the activity on the target body is greatly improved, and the poisonous effect is rapidly degraded at the same time, which avoids the Persistent residues in the environment. The mechanism of action of photoactivated drugs is novel and unique. It mainly generates activated intermediates or singlet oxygen through photoactivation, destroys various biofilms in organisms, and has multiple targets, so the targets are not easy to produce drug resistance. Photoactive drugs mainly include xanthenes, phenothiazines, furanocoumarins, thiophenes, polyynes, acridines, etc. [0003] Most of the pho...

Claims

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Application Information

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IPC IPC(8): C07D333/22C07D409/14A01N43/10A01N43/30A01N43/40A01P7/00A01P13/00A01P3/00A01P1/00
Inventor 徐汉虹宋德寿廖绍裕
Owner SOUTH CHINA AGRI UNIV
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