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Upstream product

• 110-89-4 piperidine 
• 98-86-2 acetophenone 
• 1075-06-5 2,2-dihydroxy-1-phenyl-ethanone 
• 2461-80-5 diphenacyl sulfide 
• 1816-88-2 2-azido-1-phenylethan-1-one 
• 70-11-1 α-bromoacetophenone 
• 614-21-1 2-nitroacetophenone 
• 4452-12-4 1-phenyl-3-(piperidin-1-yl)prop-2-en-1-one 
• 779-52-2 1-phenyl-2-piperidin-1-yl-ethanone 

Relevant academic research and scientific papers

Efficient Synthesis of α-Ketothioamides From α-Nitroketones, Amines or DMF and Elemental Sulfur Under Oxidant-Free Conditions

We have developed a practical, general protocol for denitration of readily available α-nitroketones with sulfur and amines to access a broad range of α-ketothioamides under mild conditions. Such a reaction proceeds under metal-, oxidant-, and catalyst-free conditions to provide synthetically useful α-ketothioamides. Furthermore, the mild reaction conditions tolerate a wide range of substrates especially for the synthesis of aliphatic α-ketothioamides which are rarely reported.

Structure–activity relationships (SARs) of α- ketothioamides as inhibitors of phosphoglycerate dehydrogenase (PHGDH)

For many years now, targeting deregulation within cancer cells’ metabolism has appeared as a promising strategy for the development of more specific and efficient cancer treatments. Recently, numerous reports highlighted the crucial role of the serine synthetic pathway, and particularly of the phosphoglycerate dehydrogenase (PHGDH), the first enzyme of the pathway, to sustain cancer progression. Yet, because of very weak potencies usually in cell-based settings, the inhibitors reported so far failed to lay ground on the potential of this approach. In this paper, we report a structure–activity relationship study of a series of α-ketothioamides that we have recently identified. Interestingly, this study led to a deeper understanding of the structure–activity relationship (SAR) in this series and to the identification of new PHGDH inhibitors. The activity of the more potent compounds was confirmed by cellular thermal shift assays and in cell-based experiments. We hope that this research will eventually provide a new entry point, based on this promising chemical scaffold, for the development of therapeutic agents targeting PHGDH.

Metal-Free C-N or C-C Bond Cleavages of α-Azido Ketones: An Oxidative-Amidation Strategy for the Synthesis of α-Ketothioamides and Amides

A novel metal-free oxidative-amidation strategy for the synthesis of α-ketothioamides and amides from α-azido ketones was developed. The C-H bond thionation of α-azido ketones with elemental sulfur could form α-ketothioacyl azide, which was then nucleophilically attacked by amines, causing the cleavage of the C-N bond to afford α-ketothioamides, while amides could be formed with the release of nitrogen gas and cyano anion in the presence of PhI(OAc)2 by selective C-C bond cleavage.

Synthesis of α-Keto Thioamides by Metal-Free C-C Bond Cleavage in Enaminones Using Elemental Sulfur

An unprecedented method for cleaving the C-C bond in N,N-disubstituted enaminones in the presence of elemental sulfur and N,N-dimethyl-4-aminopyridine is disclosed. Without using any metal catalyst or additive, the cascade functionalization of both C?C an

Methyl ketone break-and-rebuild: A strategy for full α-heterofunctionalization of acetophenones

The Willgerodt reaction under iron-catalyzed aerobic conditions was found to be an excellent tool for full α-heterofunctionalization of acetophenones with sulfur and amines. Via this break-and rebuild strategy, a wide range of thioglyoxamides was synthesi

Direct synthesis of α-ketothioamides from aryl methyl ketones and amines via I2-promoted sp3 C-H functionalization

A domino reaction that involves the formation of CS and C-N bonds in one process via sp3 C-H functionalization strategy has been developed. This reaction affords an efficient and direct method for the synthesis of α-ketothioamides from aryl met

Na2S-mediated thionation: An efficient access to secondary and tertiary α-ketothioamides via Willgerodt-Kindler reaction of readily available arylglyoxals with amines

The task of this paper is to provide an efficient process for synthesis of secondary and tertiary α-ketothioamides via Willgerodt-Kindler reaction of readily available arylglyoxals with amines using Na2S as an effective catalyst. A plausible role for Na2S in the reaction of arylglyoxals with primary amines is proposed.

Reactions of diphenacylaniline and diphenacyl sulfide under Gewald conditions: Generation of enamines and thioamides

The 1,5-diketone, diphenacylaniline, yielded an enamine under Gewald conditions, while another 1,5-diketone, diphenacyl sulfide, resulted in thioamide formation under identical conditions. 2-Amino-4-(3-oxo-1,3- diphenylpropyl)-4,5,6,7-tetrahydrobenzo[b]th

Synthesis of α-ketothioamides via willgerodt-kindler reaction of arylglyoxals with amines and sulfur under solvent-free conditions

Willgerodt-Kindler reaction of arylglyoxal hydrates with secondary amines and elemental sulfur under solvent-free conditions at 80 °C is developed, in which α-ketothioamides are obtained in 70-90% yield in 0.6-1 hour. The X-ray crystal-structure analysis for one compound was obtained. Georg Thieme Verlag Stuttgart . New York.

Willgerodt-Kindler reaction of arylglyoxals with amines and sulfur in aqueous media: A simple and efficient synthesis of -ketothioamides

A simple and efficient method for the synthesis of -ketothioamides via the Willgerodt-Kindler reaction is developed. Reactions were carried out between arylglyoxal hydrates, amines and elemental sulfur in water at 80°C to afford corresponding -ketothioamides in good to high yields in a short reaction time.