1027336-16-8

Upstream product

• 37517-81-0 3-chloro-3-oxopropanoic acid methyl ester 
• 15028-44-1 DL-phenylalanine methyl ester 
• 150-30-1 Phenylalanine 
• 38330-80-2 monomethyl monopotassium malonate 

Downstream Products

• 128892-60-4 methyl 5-benzyl-4-hydroxy-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate 
• 129029-32-9 (4S,5S)-5-Benzyl-2-oxo-4-hydroxypyrrolidine 
• 88517-80-0 5-benzyl-2,4-pyrrolidinedione 

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.

A short and elegant synthesis of (±)-streptopyrrolidine

A brief and efficient approach for the synthesis of (±)-5-benzyl-4- hydroxy-2-pyrrolidine () from phenylalanine racemate is described. The key step is the stereocontrolled reduction of the keto functionality of benzylated pyrrolidinone intermediate () via sodium borohydride in carboxylic acid medium furnishing both (R,R)- and (S,S)-configured diastereomers. The natural (R,R) enantiomer (), however, crystallized out from its racemic mixture. Structure of was confirmed by NMR, IR, elemental analyzer, and single crystal X-ray crystallographic techniques.

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

INHIBITORS OF UNDECAPRENYL PYROPHOSPHATE SYNTHASE

The present invention relates to compounds that are selective and/or potent inhibitors of UPPS. In addition to compounds which inhibit UPPS, the invention also provides pharmaceutical compositions comprising these compounds and methods of using these comp