Supercharge Your Innovation With Domain-Expert AI Agents!

1-arylmethyl-3-aryl-1h-pyrazole-5-carbohydrazide derivative, preparation method and application thereof

A methyl and pyrazole technology, applied in the field of pyrazole carbohydrazide derivatives and their preparation, can solve unseen problems and achieve the effect of great application and development prospects

Inactive Publication Date: 2007-12-12
SHANDONG UNIV
View PDF20 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In terms of structural modification, better biological activity can often be obtained through the reasonable combination of pharmacophore. Literature search shows that there are few reports on pyrazole carbohydrazide derivatives, especially there is no report on 1-arylmethyl-3- Aryl-1H-pyrazole-5-carbohydrazide derivatives and their applications or reports related to them

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
  • 1-arylmethyl-3-aryl-1h-pyrazole-5-carbohydrazide derivative, preparation method and application thereof
  • 1-arylmethyl-3-aryl-1h-pyrazole-5-carbohydrazide derivative, preparation method and application thereof
  • 1-arylmethyl-3-aryl-1h-pyrazole-5-carbohydrazide derivative, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Example 1: Preparation of 1-benzyl-3-phenyl-1H-pyrazole-5-carbohydrazide

[0046] 1) In a 100 mL round bottom flask, add 0.690 g potassium carbonate (0.005 mol), 1.080 g 3-phenyl-1H-pyrazole-5-carboxylic acid ethyl ester (0.005 mol), 0.633 g benzyl chloride (0.005 mol) ) and acetonitrile (25 ml), a reflux condenser was installed, and a drying tube was connected to the upper part. Heating and refluxing for 8 hours, the reaction was carried out until the raw material was completely consumed, and the reaction end point was detected by TLC. Concentrate under reduced pressure, remove the solvent, add ethyl acetate (30 mL) to dissolve the product, filter, concentrate the filtrate, and use ethyl acetate-petroleum ether (V / V=1 / 2) as the eluent to separate the residue by silica gel column chromatography ( 100-200 mesh silica gel) to obtain 1-benzyl-3-phenyl-1H-pyrazole-5-carboxylic acid ethyl ester with a yield of 79%.

[0047] 2) Add 1.2 ml of 80% hydrazine hydrate to 0.336 g...

Embodiment 2

[0060] Example 2: Preparation of 1-(4-tert-butylbenzyl)-3-phenyl-1H-pyrazole-5-carbohydrazide

[0061] 1) In a 100 mL round bottom flask, add 0.690 g potassium carbonate (0.005 mol), 1.080 g 3-phenyl-1H-pyrazole-5-carboxylic acid ethyl ester (0.005 mol), 0.913 g p-tert-butylbenzyl Chlorine (0.005 mol) and acetonitrile (25 mL) were installed in a reflux condenser with a drying tube at the top. It was heated to reflux for 6 hours, and the reaction was carried out until the starting material was completely consumed, and the reaction end was detected by TLC. Concentrate under reduced pressure, remove the solvent, add ethyl acetate (30 mL) to dissolve the product, filter, concentrate the filtrate, and use ethyl acetate-petroleum ether (V / V=1 / 2) as the eluent to separate the residue by silica gel column chromatography ( 100-200 mesh silica gel) to obtain 1-(4-tert-butylbenzyl)-3-phenyl-1H-pyrazole-5-carboxylic acid ethyl ester with a yield of 80%.

[0062] 2) To a solution of 0.36...

Embodiment 3

[0075] Example 3: Preparation of 1-(3-(6-chloropyridine)methyl)-3-phenyl-1H-pyrazole-5-carbohydrazide

[0076] 1) In a 100 ml round bottom flask, add 0.690 g potassium carbonate (0.005 mol), 1.080 g 3-phenyl-1H-pyrazole-5-carboxylic acid ethyl ester (0.005 mol), 0.810 g 2-chloro-5- Chloromethylpyridine (0.005 mol) and acetonitrile (25 mL) were installed in a reflux condenser, and the upper part was connected to a drying tube. The mixture was heated to reflux for 4 hours, and the reaction was carried out until the starting material was completely consumed, and the end of the reaction was detected by TLC. Concentrate under reduced pressure, remove the solvent, add ethyl acetate (30 mL) to dissolve the product, filter, concentrate the filtrate, and use ethyl acetate-petroleum ether (V / V=1 / 2) as the eluent to separate the residue by silica gel column chromatography ( 100-200 mesh silica gel) to obtain 1-(3-(6-chloropyridine)methyl)-3-phenyl-1H-pyrazole-5-carboxylic acid ethyl est...

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

PropertyMeasurementUnit
Melting pointaaaaaaaaaa
Melting pointaaaaaaaaaa
Melting pointaaaaaaaaaa
Login to View More

Abstract

The invention relates to 1- aryl methyl- 3- arylamine - 1H- pyrazole- 5- carbonhydrazides derivant in general formula (I). R1 represents hydrogen, alkyl group of C1 to C4, alkoxy, halide or nitro; R2 represents hydrogen, alkyl group of C1 to C4, alkoxy, halide or nitro; X represents carbon or nitrogen. The invention aslo relates to a method for synthesizing, separating and purifying said compound. Said method comprises following steps: taking aryl chloride and 3- arylamine - 1H- pyrazole- 5- ethyl formate as raw material, refluxing it in polar solution with potash existence and preparing derivant of 1- aryl methyl- 3- arylamine - 1H- pyrazole- 5- carboxylate, mixing said derivant with hydrazine hydrate in polar solution for reaction and getting 1- aryl methyl- 3- arylamine - 1H- pyrazole- 5- carbonhydrazides derivant. The invention aslo relates to the application of said product for preparing medicine for promoting lung carcinoma A549 cell withering.

Description

technical field [0001] The present invention relates to pyrazole carbohydrazide derivatives and a preparation method and application thereof, in particular to 1-arylmethyl-3-aryl-1H-pyrazole-5-carbohydrazide derivatives and methods for their synthesis, separation and purification with application. Background technique [0002] Pyrazole derivatives and carbohydrazide derivatives are two very important compounds, which have received extensive attention in the development of new drugs. [0003] Pyrazole compounds have anti-inflammatory, analgesic, antipyretic, bacteriostatic, bactericidal, anti-hyperglycemic, anti-cancer, anti-coagulant and other pharmacological activities, for example: pyrazole derivatives described in patents JP5017470, US5134142, WO96 / 03385 Has anti-inflammatory, anti-rheumatic, anti-bacterial, anti-viral pharmacological activities; the 4,5-aryl / heterocyclic aryl substituted pyrazoles involved in patent US4000281 have anti-RNA and DNA viruses such as myxovi...

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): C07D231/14C07D401/06A61K31/415A61K31/4439A61P35/00
Inventor 赵宝祥苗俊英张尚立夏永董志武
Owner SHANDONG UNIV
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

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

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com