341027-48-3

Upstream product

• 18598-63-5 L-cysteine methyl ester hydrochloride 
• 5442-34-2 ethyl 2-phenylacetimidate hydrochloride 
• 140-29-4 phenylacetonitrile 

Downstream Products

• 341027-49-4 (3R)-7-methyl-5-oxo-8-phenyl-2,3-dihydro-5H-thiazolo[3,2-a]pyridine-3-carboxylic acid methyl ester 
• 341027-36-9 (3R)-7-(naphthalen-1-ylmethyl)-5-oxo-8-phenyl-2,3-dihydro-5H-thiazolo[3,2-a]pyridine-3-carboxylic acid methyl ester 
• 341027-37-0 7-naphthalen-1-ylmethyl-5-oxo-8-phenyl-2,3-dihydro-5H-thiazolo[3,2-a]pyridine-3-carboxylic acid 
• 1057694-50-4 (3R)-2,3-dihydro-7-(3-methylbutyl)-5-oxo-8-phenyl-thiazolo[3,2-a]pyridine-3-carboxylic acid methyl ester 
• 1257337-61-3 (R)-methyl 7-(4-fluorobenzyl)-2,3-dihydro-5-oxo-8-phenylthiazolo[3,2-a]pyridine-3-carboxylate 
• 1257337-58-8 (R)-methyl 2,3-dihydro-5-oxo-8-phenyl-7-(1-phenylethyl)thiazolo[3,2-a]pyridine-3-carboxylate 
• 1257337-59-9 (R)-methyl 2,3-dihydro-5-oxo-8-phenyl-7-(o-tolylmethyl)thiazolo[3,2-a]pyridine-3-carboxylate 
• 1257337-60-2 (R)-methyl 7-(2-methoxybenzyl)-2,3-dihydro-5-oxo-8-phenylthiazolo[3,2-a]pyridine-3-carboxylate 
• 1257337-57-7 (R)-methyl 7-benzyl-2,3-dihydro-5-oxo-8-phenylthiazolo[3,2-a]pyridine-3-carboxylate 
• 1380299-26-2 (3R)-methyl 7-((7-methoxy-2-oxo-2H-chromen-4-yl)methyl)-5-oxo-8-phenyl-3,5-dihydro-2H-thiazolo[3,2-a]pyridine-3-carboxylate 
• 1374967-35-7 (3R)-7-((2,3-dimethylphenoxy)methyl)-5-oxo-8-phenyl-3,5-dihydro-2H-thiazolo[3,2-a]pyridine-3-carboxylic acid 
• 1374967-34-6 (3R)-7-(3-methylphenethyl)-5-oxo-8-phenyl-3,5-dihydro-2H-thiazolo[3,2-a]pyridine-3-carboxylic acid 

Relevant academic research and scientific papers

Mapping pilicide anti-virulence effect in Escherichia coli, a comprehensive structure-activity study

Pilicides prevent pili formation and thereby the development of bacterial biofilms in Escherichia coli. We have performed a comprehensive structure activity relationship (SAR) study of the dihydrothiazolo ring-fused 2-pyridone pilicide central fragment by varying all open positions. Orthogonal projections to latent structures discriminant analysis (OPLS-DA) was used to distinguish active from inactive compounds in which polarity proved to be the most important factor for discrimination. A quantitative SAR (QSAR) partial least squares (PLS) model was calculated on the active compounds for prediction of biofilm inhibition activity. In this model, compounds with high inhibitory activity were generally larger, more lipophilic, more flexible and had a lower HOMO. Overall, this resulted in both highly valuable SAR information and potent inhibitors of type 1 pili dependent biofilm formation. The most potent biofilm inhibitor had an EC50 of 400 nM.

An enantioselective ketene-imine cycloaddition method for synthesis of substituted ring-fused 2-pyridinones

Previously, a method for the stereoselective synthesis of β-lactams, starting from 2H-δ2-thiazolines and Meldrum's acid derivatives, has been reported from our laboratory. We now report a new method for the synthesis of optically active, highly substituted ring-fused 2-pyridinones. This was discovered when 2-alkyl-δ2-thiazolines and Meldrum's acid derivatives were treated with HCl(g) in benzene at 5 → 78 °C. Further refinement of the synthetic protocol revealed that use of 1,2-dichloroethane as solvent at 0 → 64 °C led to the desired 2-pyridinones in good yields and with excellent enantioselectivity. Use of these conditions allowed preparation of 2-pyridinones from several different δ2-thiazolines and Meldrum's acid derivatives and may be a general route to 2-pyridinones.