147353-99-9

Upstream product

• 2900-27-8 2-(tert-butoxycarbonylamino)-2-phenylacetic acid 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 

Downstream Products

• 819796-92-4 (R)-2-tert-butoxycarbonylamino-1,2-diphenylethanone 
• 1359983-69-9 C₂₅H₃₃NO₃ 
• 1359983-76-8 C₂₁H₂₅N₃*ClH 
• 153788-02-4 DL-1-Amino-1-phenyl-undecan-2-on-hydrochlorid 
• 1351299-60-9 1-(tert-butoxycarbonylamino)-1-phenylundecan-2-one 

Relevant academic research and scientific papers

Catalytic α-Deracemization of Ketones Enabled by Photoredox Deprotonation and Enantioselective Protonation

This study reports the catalytic deracemization of ketones bearing stereocenters in the α-position in a single reaction via deprotonation, followed by enantioselective protonation. The principle of microscopic reversibility, which has previously rendered this strategy elusive, is overcome by a photoredox deprotonation through single electron transfer and subsequent hydrogen atom transfer (HAT). Specifically, the irradiation of racemic pyridylketones in the presence of a single photocatalyst and a tertiary amine provides nonracemic carbonyl compounds with up to 97% enantiomeric excess. The photocatalyst harvests the visible light, induces the redox process, and is responsible for the asymmetric induction, while the amine serves as a single electron donor, HAT reagent, and proton source. This conceptually simple light-driven strategy of coupling a photoredox deprotonation with a stereocontrolled protonation, in conjunction with an enrichment process, serves as a blueprint for other deracemizations of ubiquitous carbonyl compounds.

Identification of Anti-Mycobacterial Biofilm Agents Based on the 2-Aminoimidazole Scaffold

Tuberculosis (TB) remains a significant global health problem for which new therapeutic options are sorely needed. The ability of the causative agent, Mycobacterium tuberculosis, to reside within host macrophages and form biofilm-like communities contributes to the persistent and drug-tolerant nature of the disease. Compounds that can prevent or reverse the biofilm-like phenotype have the potential to serve alongside TB antibiotics to overcome this tolerance, and decrease treatment duration. Using Mycobacterium smegmatis as a surrogate organism, we report the identification of two new 2-aminoimidazole compounds that inhibit and disperse mycobacterial biofilms, work synergistically with isoniazid and rifampicin to eradicate preformed M. smegmatis biofilms in vitro, are nontoxic toward Galleria mellonella, and exhibit stability in mouse plasma.

Small molecule probes of the receptor binding site in the Vibrio cholerae CAI-1 quorum sensing circuit

Based on modification of separate structural features of the Vibrio cholerae quorum sensing signal, (S)-3-hydroxytridecan-4-one (CAI-1), three focused compound libraries have been synthesized and evaluated for biological activity. Modifications to the acyl tail and α-hydroxy ketone typically provided agonists with activities correlated to tail length and conservative changes to the hydroxy ketone. Among the molecules identified within this collection of agonists is Am-CAI-1 (B11), which is among the most potent agonists reported to date with an EC50 of 0.21 μM. Modifications to the ethyl side chain delivered molecules with both agonist and antagonist activity, including m-OH-Ph-CAI-1 (C13) which is the most potent antagonist reported to date with an IC50 of 36 μM. The molecules described in this manuscript are anticipated to serve as valuable tools in the study of quorum sensing in Vibrio cholerae and provide new leads in the development of an antivirulence therapy against this human pathogen.

Asymmetrie imino aza-enamine reaction catalyzed by axially chiral dicarboxylic acid: Use of arylaldehyde N,N-dialkylnydrazones as acyl anion equivalent

Synthetic utility of arylaldehyde N,N-dialkylhydrazones as a practical acyl anion equivalent could be exploited for the first time in the asymmetric imino aza-enamine reaction catalyzed by axially chiral carboxylic acid. Copyright