928-73-4

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
[(aminocarbonyl)hydrazono]acetic acid is utilized as a key building block for the synthesis of a variety of pharmaceuticals and agrochemicals. Its unique structure allows for the creation of diverse compounds with potential therapeutic and agricultural applications.
Used in Medicinal Chemistry and Drug Development:
As a reagent, [(aminocarbonyl)hydrazono]acetic acid is employed in the preparation of hydrazone derivatives, which are valuable in medicinal chemistry and drug development. These derivatives can exhibit a range of biological activities, making them useful in the discovery and design of new drugs.
Used in Antitumor Research:
[(aminocarbonyl)hydrazono]acetic acid has been studied for its potential as an anti-tumor agent. It demonstrates the ability to inhibit the growth of cancer cells, which makes it a promising candidate for further research and development in oncology.
Used in Drug Delivery Systems:
While not explicitly mentioned in the provided materials, given its potential as an anti-tumor agent, it is plausible that [(aminocarbonyl)hydrazono]acetic acid could also be incorporated into drug delivery systems to improve the targeted delivery of anti-cancer treatments, enhancing their efficacy and reducing side effects.

InChI:InChI=1/C3H5N3O3/c4-3(9)6-5-1-2(7)8/h1H,(H,7,8)(H3,4,6,9)

Upstream product

• 302-17-0 chloral hydrate 
• 563-41-7 semicarbazide hydrochloride 
• 75-87-6 chloral 
• 4426-72-6 hydrazine carboxamide 
• 298-12-4 Glyoxilic acid 
• 79-43-6 dichloro-acetic acid 

Downstream Products

• 461-89-2 6-azauracil 
• 80305-82-4 C₁₀H₉Cl₂N₃O₃ 
• 80305-81-3 C₁₀H₉Cl₂N₃O₃ 
• 80305-79-9 glyoxylic acid 2-(4-chlorobenzyl)semicarbazone 
• 100-52-7 benzaldehyde 
• 80305-80-2 C₁₀H₁₀ClN₃O₃ 
• 74-90-8 hydrogen cyanide 
• 64-19-7 acetic acid 

Relevant academic research and scientific papers

An improved synthesis of the 5-HT1A receptor agonist Eptapirone free base

Eptapirone free base, F11440,4-methyl-2-(4-(4-(pyrimidin-2-yl)piperazin-1-yl)butyl)-1,2,4-triazine-3,5(2H,4H)-dione, represents a potent and selective 5-HT1A receptor agonist with high efficacy and the potential to regulate anxiety disorders. Herein, we report a method to retro-synthesize eptapirone free base. The compound consists of heterocyclic aromatic portion and aliphatic portion, and the synthetic route consisted of a total of nine steps with an overall yield of 8.8% starting from the commercially available materials. The key steps in the synthetic method involved: (1) using sodium hydroxide and ethylene glycol as solvent resulted in a better cyclization and yield (61.6%) of 1,2,4-triazine-3,5(2H,4H)-dione; (2) an acceptable yield (63.1%) of 4-tert-butyl(pyrimidin-2-yl)piperazine-1-carboxylate was obtained under an optimized conditions of using triethylamine as a base, ethanol as a solvent, and a reaction temperature of 50?°C for 16?h with non-metal catalysis and less byproducts; (3) the reaction step of eptapirone could get a better yield (49.6%) with an optimized condition of potassium carbonate as a base, acetonitrile as a solvent, NaI as a catalyst, and a reaction temperature of 50?°C for 12?h by nucleophilic substitution reaction. The main advantages of this route were an acceptable product purity, the commercial availability of all starting materials and the absence of high temperature, high pressure and noble metal catalysts, which could result in more feasible commercial applications.

Full synthesis method of eptapirone

The invention discloses a full synthesis method of eptapirone. The full synthesis method comprises the following steps: (1) taking aminourea hydrochloride and trichloracetic aldehyde as raw materialsand carrying out a series of reaction to obtain 2-[2-(aminocarbonyl)hydrazono](CD-1); (2) synthesizing 6-azauracil(CD-2) by the 2-[2-(aminocarbonyl)hydrazono] under the action of sodium hydroxide; (3)taking the 6-azauracil and acetic anhydride to react to obtain 2-acetyl-2H-[1,2,4]triazine-3,5(2H,4H)-diketone(CD3); (4) taking the 2-acetyl-2H-[1,2,4]triazine-3,5(2H,4H)-diketone to react to obtain3-methyl-6-azauracil(CD-4); (5) taking the 3-methyl-6-azauracil to react to obtain 2-(4-chlorobutyl)-4-methyl-1,2,4-triazine-3,5(2H,4H)-diketone(CD-5); (6) taking 2-bromopyrimidine, 1-Boc-piperazine and triethylamine to react to obtain 4-(pyrimidine-2-yl)piperazine-1-tert-butyl formate(CD-6); furthermore, reacting to obtain 2-(1-piperazinyl)pyrimidine hydrochloride (1 to 1)(CD-7); (7) taking the 2-(4-chlorobutyl)-4-methyl-1,2,4-triazine-3,5(2H,4H)-diketone in step (5) to react with the 2-(1-piperazinyl)pyrimidine hydrochloride in step (6) to obtain the eptapirone(CD-8). The product disclosed by the invention is high in purity and yield and is suitable for industrialized production.

Synthesis of novel 3-substituted-5H-benzo[5,6][1, 4]thiazino[3,2-e][1,2,4]triazines and their 15-lipoxygenase inhibitory activity

A new group of 3-substituted-5H-benzo[5,6][1,4]thiazino[3,2-e][1,2,4]triazines was designed, synthesized and evaluated as inhibitors of 15-lipoxygenase (15-LO), and the results were compared with those of standard ligand 4-methyl-2-(4-methylpiperazin-1-yl)pyrimido[4,5-b][1,4]benzothiazine (4-MMPB). Among the newly designed ligands, compound 9e showed the best IC50 of 15-LO inhibition (IC50?=?38?μM). The docking calculations were performed in MOE software based on the function of force-field scoring, in order to study the interaction of these new compounds and standard ligand with 15-LO. The docking study implied that these ligands have hydrogen bond interaction with the residue of active site of 15-LO.

Substitutes 2-aryl-1,2,4-triazine-3,5-di(thi)one

The invention relates to novel substituted 2-aryl-1,2,4-triazine-3,5-di(thi)ones of the general formula (I), in which Q1, Q2, R1, R2, R3, R4, R5 and R6 are each as defined in the description, and to processes for their preparation and to their use as herbicides.

Preparation of α-(2,2-diphenylhydrazino)lactones and related compounds by radical cyclization: Use of glyoxylic acid hydrazone derivatives

Glyoxylic acid diphenylhydrazone (2a) and the corresponding O-benzyloxime (2b) are easily esterified in high yield by β-bromo alcohols. The resulting esters undergo radical cyclization to α-(2,2-diphenylhydrazino)- or α-[(phenylmethoxy)amino]lactones on treatment with tributyltin hydride. Esters for radical cyclization were also made using a β-(phenylseleno) alcohol and an enol ether. Several derivatives of glyoxylic acid were evaluated, but none was as effective as 2a or 2b. The imine 28 was prepared by an indirect route; it undergoes radical cyclization with displacement of the nitrogen substituent (28 → 30) so that an α-amino lactone can be generated by acid hydrolysis of the cyclization product.