129221-15-4

Upstream product

• 13433-00-6 diethyl aminomalonate hydrochloride 
• 122-04-3 4-nitro-benzoyl chloride 
• 62-23-7 4-nitro-benzoic acid 
• 6829-40-9 aminomalonic acid diethyl ester 

Downstream Products

• 1379481-88-5 (E)-2-(p-nitrophenyl)-4,4-bis(ethoxycarbonyl)-5-dimethoxyphosphorylmethylidene-1,3-oxazoline 
• 1379481-83-0 (Z)-2-(p-nitrophenyl)-4,4-bis(ethoxycarbonyl)-5-dimethoxyphosphorylmethylidene-1,3-oxazoline 
• 902781-51-5 1-(4-nitrobenzoyl)piperidine-2,2-dicarboxylic acid diethyl ester 
• 129221-16-5 2,2-diethoxycarbonyl-4-hydroxy-1-(4-nitrobenzoyl)pyrrolidine 
• 129221-17-6 2,2-diethoxycarbonyl-2,3-dihydro-1-(4-nitrobenzoyl)-1H-pyrrole 
• 129221-18-7 2-ethoxycarbonyl-4-hydroxy-2-hydroxymethyl-1-(4-nitrobenzyl)pyrrolidine 
• 902781-44-6 1-(4-nitrobenzoyl)piperidine-2,2-dicarboxylic acid monoethyl ester 

Relevant academic research and scientific papers

An optimised series of substituted N-phenylpyrrolamides as DNA gyrase B inhibitors

ATP competitive inhibitors of DNA gyrase and topoisomerase IV have great therapeutic potential, but none of the described synthetic compounds has so far reached the market. To optimise the activities and physicochemical properties of our previously reported N-phenylpyrrolamide inhibitors, we have synthesized an improved, chemically variegated selection of compounds and evaluated them against DNA gyrase and topoisomerase IV enzymes, and against selected Gram-positive and Gram-negative bacteria. The most potent compound displayed IC50 values of 6.9 nM against Escherichia coli DNA gyrase and 960 nM against Staphylococcus aureus topoisomerase IV. Several compounds displayed minimum inhibitory concentrations (MICs) against Gram-positive strains in the 1–50 μM range, one of which inhibited the growth of Enterococcus faecalis, Enterococcus faecium, S. aureus and Streptococcus pyogenes with MIC values of 1.56 μM, 1.56 μM, 0.78 μM and 0.72 μM, respectively. This compound has been investigated further on methicillin-resistant S. aureus (MRSA) and on ciprofloxacin non-susceptible and extremely drug resistant strain of S. aureus (MRSA VISA). It exhibited the MIC value of 2.5 μM on both strains, and MIC value of 32 μM against MRSA in the presence of inactivated human blood serum. Further studies are needed to confirm its mode of action.

Organocatalyzed route to enantioenriched pipecolic esters: decarboxylation of an aminomalonate hemiester

Enantioenriched pipecolic esters were prepared in good yields in the decarboxylation, at room temperature, of N-protected piperidinohemimalonates catalyzed by cinchona alkaloids. Enantiomeric excesses as high as 72% were obtained when using 9-epi-cinchonine and the N-benzoyl substituted piperidinohemimalonate. A detailed study of the different reaction parameters revealed that the selectivity of this noncovalent organocatalyzed reaction is strongly dependent on the solvent, toluene or carbon tetrachloride being the best ones. The whole process based on the malonic acid synthesis was successfully tested on a 10 mmolar scale and established a practical alternative to the asymmetric protonation of lithium enolates.