Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Compound with piperine skeleton structure as well as preparation and application thereof

A skeleton compound, piperine technology, applied in the field of agricultural pest control, can solve the problems of heavy workload, long time-consuming, high cost, etc., and achieve the effect of low difficulty, novel skeleton and easy synthesis

Active Publication Date: 2020-06-12
CHINA AGRI UNIV
View PDF3 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The conventional method of drug screening is high-throughput screening, that is, to find new potential lead compounds through pharmacological experimental model screening for a large number of compounds, but this random method is heavy in workload, time-consuming, high in cost, and has certain blindness

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
  • Compound with piperine skeleton structure as well as preparation and application thereof
  • Compound with piperine skeleton structure as well as preparation and application thereof
  • Compound with piperine skeleton structure as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1: the preparation of the piperonyl compound I-1-(3) containing angelica lactone

[0035] Add raw material 1 (1.22g, 8.0mmol), DCM 50ml and manganese dioxide (6.96g, 80mmol) into a 250ml three-necked reaction flask, stir and react at room temperature for 2-5h, and monitor the completion of the reaction by TLC. Diatomaceous earth was filtered to remove manganese dioxide, and the filtrate was concentrated under reduced pressure to obtain white solid 3,4-methylenedioxybenzaldehyde 2 (1.12 g, 7.46 mmol), with a yield of 93.25%.

[0036]

[0037] Add raw material 3 (539mg, 2.1mmol), acetic anhydride (3.84g, 37.8mmol) and THF10ml into a 50ml reaction flask, stir at room temperature for 10min, add 3 drops of concentrated sulfuric acid, continue stirring for 2-3h, monitor the reaction by TLC Finish. Add an appropriate amount of water, continue to stir and react for 15-20 minutes, concentrate under reduced pressure, add an appropriate amount of methanol, and a lar...

Embodiment 2

[0044] Embodiment 2: Preparation of piperonyl ring compound I-2-(10) containing thiothiazolidinone

[0045] Synthesis of 3,4-methylenedioxybenzaldehyde 2:

[0046]

[0047] Add raw material 1 (1.22g, 8.0mmol), DCM 50ml and manganese dioxide (6.96g, 80mmol) into a 250ml three-necked reaction flask, stir and react at room temperature for 2-5h, and monitor the completion of the reaction by TLC. Diatomaceous earth was filtered to remove manganese dioxide, and the filtrate was concentrated under reduced pressure to obtain white solid 3,4-methylenedioxybenzaldehyde 2 (1.12 g, 7.46 mmol), with a yield of 93.25%.

[0048] Synthesis of 3,4-methylenedioxycinnamaldehyde 6:

[0049]

[0050] Add raw material 2 (450 mg, 3 mmol), raw material 3 (916 mg, 3.01 mmol) and 20 ml of toluene into a 100 ml three-necked reaction flask, heat up to 80-100 ° C for 20-24 h. After the reaction was completed, it was cooled to room temperature, and unreacted raw material 5 was removed by filtration...

Embodiment 3

[0060] Example 3: Determination of Enzyme Inhibitory Activity of Compounds with Piperine Skeleton Structure

[0061] With MU-(GlcNAc) 2 As substrate, 20mM sodium chloride and 20mM sodium dihydrogen phosphate mixed solution are used as buffer solution, and experimental group and control group (+), control group (-) are set, and three repetitions are established in each group. Experimental group: In the standard reaction system, 2 μL of a certain concentration of compound and 88 μL of OfCht-I, OfChi-H, OfHex1, HsChit1 and buffer premix, incubated at 30°C for 10 minutes, then added 10 μL of substrate, and incubated at 30°C After 20 minutes, 100 μL of 0.5 M sodium carbonate was added to terminate the reaction, and the released MU was detected by a fluorescence detector for its absorption value A, with an excitation wavelength of 360 nm and an emission wavelength of 460 nm. Control group (+): 2 μL of DMSO was used to replace 2 μL of a certain concentration of the compound, and the...

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 discloses a compound with a piperine skeleton structure as well as preparation and application of the compound, wherein the structural formulas of the compound are shown as a formula I-1and a formula I-2; in the formulas, R1 is hydrogen, halogen, nitryl or cyano, or substituted or unsubstituted hydroxyl, amino, carboxyl, ester group, hydrosulfenyl, acylamino, ureido, C1-C5 straight-chain or branched-chain alkyl and C1-C5 alkoxy; R2 is hydrogen, halogen, nitro or cyano, or substituted or unsubstituted hydroxyl, amino, carboxyl, ester group, hydrosulfenyl, acylamino, ureido, phenyl, aryl and aromatic heterocyclic group, or substituted or unsubstituted C1-C5 straight-chain or branched-chain alkyl, or substituted or unsubstituted C1-C5 alkoxy, or substituted or unsubstituted C6-C30 aryl, fused ring and fused heterocyclic ring. As a chitinase inhibitor, the compound provided by the invention has the advantages of high activity, good broad spectrum and easiness in synthesis, and shows excellent insecticidal ability and insecticidal spectrum.

Description

technical field [0001] The invention belongs to the technical field of agricultural pest control, and in particular relates to the preparation of multiple chitinase inhibitors containing a piperine skeleton compound and its application in agricultural pest control. Background technique [0002] At present, agricultural pest control is mainly based on chemical control. However, with the long-term irrational use of chemical pesticides, a series of problems have been caused, such as pest resistance, environmental pollution, and the safety of humans, animals, natural enemies, and non-target organisms. Therefore, it is urgent to research and develop efficient and environmentally friendly new green pesticides for the guarantee of the quality and safety of modern agricultural products. Insect growth regulators can interfere with the unique growth and development process of insects in a targeted manner, and are safe to natural enemies and non-target organisms. They are called "thir...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C07D407/06C07D417/06A01N43/30A01N43/78A01P7/00A01P7/02A01P7/04
CPCC07D407/06C07D417/06A01N43/30A01N43/78Y02A50/30
Inventor 段红霞韩清杨青吴楠朱凯王金娥李慧琳
Owner CHINA AGRI UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com