30866-24-1

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl malonyl hydrazide is used as a starting reagent for the step-wise construction of complex pyrrole-pyrazole systems. These systems are essential in the development of new pharmaceutical compounds with potential therapeutic applications.
Used in Chemical Synthesis:
Ethyl malonyl hydrazide is used as a key intermediate in the synthesis of 4,5-dihydro-1H-pyrazoles. This application involves two methods: conventional thermal heating and microwave-assisted methods. The synthesized pyrazoles can be utilized in various chemical and pharmaceutical applications.
Used in Research and Development:
Ethyl malonyl hydrazide is used as a building block in the synthesis of pyrazolopyridazine, a compound with potential applications in the development of new drugs and materials. Researchers can explore the properties and potential uses of Ethyl malonyl hydrazide in various industries, including pharmaceuticals and materials science.

InChI:InChI=1/C5H10N2O3/c1-2-10-5(9)3-4(8)7-6/h2-3,6H2,1H3,(H,7,8)

Upstream product

• 105-53-3 diethyl malonate 
• 140-87-4 Cyanoacetohydrazide 
• 1846-76-0 ethyl coumarin-3-carboxylate 
• 137786-67-5 ethyl 3-amino-2-ethoxycarbonyl-2-butenoate 
• 64-17-5 ethanol 

Downstream Products

• 127382-11-0 N'-benzylidene-2-(ethoxycarbonyl)acetohydrazide 
• 4744-71-2 pyrazolidine‐3,5‐dione 
• 839724-80-0 ethyl 3-(2-{[(3R,5S)-1-(3-acetoxy-2,2-dimethylpropyl)-7-chloro-5-(2,3-dimethoxyphenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl]acetyl}hydrazino)-3-oxopropionate 
• 30866-42-3 N'-(2-hydroxybenzylidene)-2-oxo-2H-chromene-3-carbohydrazide 

Relevant academic research and scientific papers

A new approach for one-pot, green synthesis of new polycyclic indoles in aqueous solution

Electro-oxidation of phenylamine derivatives (1a and 1b) have been studied in the presence of pyrazolidine-3,5-dione (3) as a nucleophile in phosphate buffer solution mixed with ethanol, using voltammetric and spectroscopic techniques. The obtained results indicated that the oxidized form of phenylamines (2a and 2b) participate in Michael addition type reactions with pyrazolidine-3,5-dione (3) and via ECECCCCC mechanisms convert to the corresponding new polycyclic indoles (12a and 12b). In the present study, new polycyclic indole derivatives were synthesized with good yields and high purity using a facile, one-pot and environmentally friendly electrochemical method, without any chemical catalysts, toxic solvents and hard conditions.

Nitramino- and Dinitromethyl-Substituted 1,2,4-Triazole Derivatives as High-Performance Energetic Materials

Since highly nitrated nitrogen-rich heterocycles are important motifs in high energy density materials, extensive studies for the development of such novel molecules have been underway. A highly energetic moiety, 3-dinitromethyl-5-nitramino-1,2,4-triazole, which consists of a triazole ring, and nitramino and dinitromethyl groups, has been designed and synthesized. By pairing with nitrogen-rich cations, several ionic derivatives were obtained. Theoretical and experimental studies show that the hydroxylammonium salt (7) is highly dense, and has excellent detonation performance with acceptable thermal stablity and sensitivities, which are superior to those of RDX.

1,8-Naphthyridines VI. Synthesis and anti-inflammatory activity of 5-(alkylamino)-N,N-diethyl[1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamides with a new substitution pattern on the triazole ring

On the basis of the good anti-inflammatory properties shown by the 9-alkyl-N,N-dialkyl-5-(alkylamino)[1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamides 1, a series of analogues of such compounds, in which the 9-alkyl substituent was replaced by an ester or amide group (compounds 3a-i), was prepared and tested (inhibition of carrageenan-induced paw edema in the rat). Also two 5-(N-alkyl,N-acylamino) derivatives (compounds 4a,b) were synthesized and evaluated for the same purpose. Even though the general trend for these new [1,2,4]triazolo[4,3-a][1,8]naphthyridine derivatives was a decrease in activity compared with compounds 1, some of the new synthesized compounds exhibited still good anti-inflammatory properties.

Synthesis and anticancer potential of certain novel 2-oxo-N'-(2-oxoindolin- 3-ylidene)-2H-chromene-3-carbohydrazides

Treatment of ethyl 3-hydrazinyl-3-oxopropanoate (6) with indoline-2,3-dione derivatives 7a-g gave ethyl 3-oxo-3-(2-(2-oxoindolin-3-ylidene)hydrazinyl) propanoates 8a-g which were allowed to react with the appropriate salicyaldehyde 9a and/or 9b to furnish the chromene-based hydrazones 10a-i. Compounds 10a-i displayed a significant activity against HT-29 colon cancer cell line and a moderate activity against leukemia K562 cell line. Compound 10f emerged as the most active congener toward HT-29 colon cancer cell line with IC50 = 7.98 ± 0.05 μM whereas compound 10c exhibited the best antiproliferative activity against leukemia K562 cell line with IC50 = 9.44 ± 0.02 μM. Moreover, compound 1e showed 87.81 ± 7% inhibition of side population (SP) HT-29 colon cancer stem cells.

Synthesis method of 5-methyl-4H-1,2,4-triazole-3-acetic acid

A synthesis method of 5-methyl-4H-1,2,4-triazole-3-acetic acid comprises steps as follows: 1) diethyl malonate and hydrazine hydrate react in an alcohol solvent at the room temperature, and a compound1 is obtained; 2) the compound 1 and methyl ethyl imino ether hydrochloride 2 react in a proper solvent in the presence of organic alkali at the reflux temperature, and a compound 3 is obtained; 3) the compound 3 hydrolyzes ester bonds in an alcohol solvent in the presence of alkali, proper acid is added for an acidizing reaction, a compound I is obtained and the reaction route is shown in the following description. The synthesis method has the advantages as follows: raw materials used in the synthesis route are easy to obtain and cheap, the synthesis process of each step has mild conditionsand industrial production is facilitated.

METALLOENZYME INHIBITOR COMPOUNDS

Provided are compounds having metalloenzyme modulating activity, and methods of treating diseases, disorders or symptoms thereof mediated by such metalloenzymes.

Synthesis and crystal structure of some 3,5-pyrazolidinediones

Syntheses of various derivatives of 3,5-pyrazolidenedione are reported. This includes 4-arylidene (alkylidene or aralkylidene)-3,5-pyrazolidinediones, which on epoxidation gave unreported oxiranes. The syntheses of these derivatives were based on either the Knoevenagel reaction of carbonyl derivatives with 3,4-pyrazolidinedione or cyclization of arylidene (alkylidene) malonic acid hydrazide with glacial acetic acid. 4-Arylazo-3,5-pyrazolidinedione derivatives were also prepared by coupling of aryldiazonium salts with 3,5-pyrazolidinedione or cyclization of arylazomalonic acid hydrazide. Reduction of 4-benzylidene derivatives gave the corresponding benzyl derivatives. The structure of the new products was confirmed by elemental and spectral analyses and X-ray crystallography.

Transformations of coumarins accompanied by intermediate opening and recyclization of the lactone ring 3. Study of the reactions of 3-ethoxy-carbonylcoumarins with cyanoacetyl-hydrazines by NMR spectroscopy

The reaction of 3-ethoxycarbonylcoumarin with derivatives of cyanoacetylhydrazine directly in the sample tube of the NMR spectrometer was investigated by 1H NMR spectroscopy. The structure of the components of the reaction mixtures was establis

Efficient synthesis of 4-ethoxycarbonyl pyrazolin-5-one derivatives

Concise and efficient methods for the preparation of 3-substituted 4-ethoxycarbonylpyrazolin-5-ones are described. The synthetic strategies involve carbon-acylation in the presence of base, followed by ring cyclization with hydrazine or hydrazine monohydrochloride.

The Complex Reaction of Acetohydrazides with Unsaturated Diketones: Alternative Cyclizations to 1,2-Diazepin-3-ones and Pyrazolopyridines

The reaction of 2-cyanoacetohydrazide (1) and 2-(ethoxycarbonyl)acetohydrazide (26) with unsaturated 1,3-diketones leading with moderate yields to 1,2-diazepinones (3, 23, 24) and pyrazolopyridines (5, 15, 20, 25) together with the corresponding acetohydrazones have been studied.The reaction course depends on the temperature and the relative reactivity of the carbonyl groups of the starting materials.When one of these carbonyl groups is less reactive (benzoyl or ethoxycarbonyl groups), the reaction does not yield diazepinones but only pyrazolopyridines and/or acetohydrazones.