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Usage

Uses

Used in Pharmaceutical Research:
2,5-dihydro-4-hydroxy-2-oxo-1H-Pyrrole-3-carboxylic acid Methyl ester is utilized as a key intermediate in the synthesis of pharmaceuticals, particularly for drugs targeting oxidative stress and inflammation. Its antioxidant and anti-inflammatory properties make it a promising candidate for the development of treatments for various diseases where these conditions are implicated.
Used in Organic Synthesis:
In the field of organic synthesis, 2,5-dihydro-4-hydroxy-2-oxo-1H-Pyrrole-3-carboxylic acid Methyl ester serves as a valuable building block for the creation of complex organic molecules. Its unique chemical structure allows for a wide range of reactions, making it suitable for the synthesis of various organic compounds.
Used in Drug Development:
2,5-dihydro-4-hydroxy-2-oxo-1H-Pyrrole-3-carboxylic acid Methyl ester is employed as a precursor in the development of new drugs, leveraging its potential therapeutic benefits. Its antioxidant and anti-inflammatory properties are being explored for the treatment of conditions where these mechanisms are crucial for disease management and prevention.
Used in Laboratory Settings:
Due to its improved solubility and stability in its methyl ester form, 2,5-dihydro-4-hydroxy-2-oxo-1H-Pyrrole-3-carboxylic acid Methyl ester is used in laboratories for research purposes. It facilitates easier handling and manipulation in experimental procedures, contributing to more efficient and effective scientific investigations.

Upstream product

• 83544-51-8 methyl hippurylmalonate 
• 313496-20-7 C₇H₁₁NO₅ 
• 67-56-1 methanol 
• 51925-56-5 ethyl 3-((2-ethoxy-2-oxoethyl)amino)-3-oxopropanoate 
• 105688-25-3 2-(2-Acetylamino-acetyl)-malonic acid dimethyl ester 
• 105688-28-6 N-Acetyl-α-carbomethoxytetramic acid 

Downstream Products

• 1005179-35-0 C₁₇H₂₀N₂O₃ 
• 37772-89-7 pyrrolidine-2,4-dione 

Relevant academic research and scientific papers

Design, synthesis and microbiological evaluation of ampicillin-tetramic acid hybrid antibiotics

Exploiting iron-uptake pathways by conjugating β-lactam antibiotics with iron-chelators, such as catechol and hydroxamic acid is a proven strategy to overcome permeability-related resistance in Gram-negative bacteria. As naturally occurring iron-chelating tetramic acids have not been previously examined for this purpose, an exploratory series of novel ampicillin-tetramic acid hybrids that structurally resemble ureidopenicillins was designed and synthesized. The new analogs were evaluated for the ability to chelate iron and their MIC activities determined against a representative panel of clinically significant bacterial pathogens. The tetramic acid β-lactam hybrids demonstrated a high affinity to iron in the order of 10 -30 M 3. The hybrids were less active against Gram-positive bacteria. However, against Gram-negative bacteria, their activity was species dependent with several hybrids displaying improved activity over ampicillin against wild-type Pseudomonas aeruginosa. The anti-Gram-negative activities of the hybrids improved in the presence of clavulanic acid revealing that the tetramic acid moiety did not provide added protection against β-lactamases. In addition, the hybrids were found to be efflux pump substrates as their activities markedly improved against pump-inactivated strains. Unlike the catechol and hydroxamic acid siderophore β-lactam conjugates, the activities of the hybrids did not improve under iron-deficient conditions. These results suggest that the tetramic acid hybrids gain permeability via different membrane receptors, or they are outcompeted by native bacterial siderophores with stronger affinities for iron. This study provides a foundation for the further exploitation of the tetramic acid moiety to achieve novel β-lactam anti-Gram-negative agents, providing that efflux and β-lactamase mediated resistance is addressed.

Studies on the synthesis and bioactivities of 4-amino derivatives of tetramic acid

In order to study the potential bioactivities of 4-amino tetramic acid derivatives, the 4-amination products of pyrrolidine-2,4-diones (5) and 4-hydroxy-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxylates (4) were prepared. The 4-amination of 5 took place in high yield when catalyzed by acetic acid, whereas the 4-amination of 4 was achieved through a 4-ethoxy intermediate, which was prepared by acidic etherification. Their herbicidal, fungicidal, insecticidal, and antitumor activities were tested. The bioassays showed that two of the compounds exhibited good herbicidal activity against dicot Arabidopsis thaliana at a concentration of 10 μg/mL, and one compound gave instinct fungicidal activity against Pythium sp. at a concentration of 2 μg/mL.

Tetramic acids as scaffolds: Synthesis, tautomeric and antibacterial behaviour

Efficient synthetic routes for tetramic acids variously substituted on the ring nitrogen, their tautomeric behaviour in solution and their antibiotic activity are reported.

Design and structure-activity relationships of potent and selective inhibitors of undecaprenyl pyrophosphate synthase (UPPS): Tetramic, tetronic acids and dihydropyridin-2-ones

Based on a pharmacophore hypothesis substituted tetramic and tetronic acid 3-carboxamides as well as dihydropyridin-2-one-3-carboxamides were investigated as inhibitors of undecaprenyl pyrophosphate synthase (UPPS) for use as novel antimicrobial agents. S

Simple route to azabicyclic peroxides from tetramic acid derivatives using manganese(III)-based molecular oxygen trapping reaction

A simple one-step synthesis of azabicyclic peroxides was achieved by the manganese(III)-mediated oxidative formal [2+2+2] cycloaddition. The reaction of alkenes (1) with pyrrolidinediones (2) was carried out with manganese(III) acetate in acetic acid at 2

Acylaminoacetyl Derivatives of Active Methylene Compounds. 2. The Cyclization of the Acetylaminoacetyl Derivatives to α-Substituted Tetramic Acids and the Formation of N-Acetyl-α-substituted Tetramic Acids

The reaction of aceturic acid p-nitrophenyl ester with active methylene compounds Y-CH2-CO2R has been found to give either the normally expected C-acylation compounds 2 (Y = -CN, -CO2R, -COCH3) or N-acetyl-α-Y-substituted tetramic acids 3 (Y = -CO2R, -COC

Acylaminoacetyl Derivatives of Active Methylene Compounds. 1. The Cyclization of the Benzoylaminoacetyl Derivatives to α-Substituted Tetramic Acids (1)

Hippuric acid was converted to α-Y-substituted tetramic acids (Y = -CN, -CO2R and -COCH3) according to the following general scheme of reactions: a) preparation of the hippuric acid chloride or of its p-nitrophenyl ester; b) C-acylation of an active methy