5509-99-9

Upstream product

• 110-91-8 morpholine 
• 98-86-2 acetophenone 
• 70-11-1 α-bromoacetophenone 
• 949-01-9 1-(morpholin-4-yl)-2-phenylethanethione 
• 100-52-7 benzaldehyde 
• 141377-54-0 2-nitro-1-phenylethan-1-ol 
• 614-21-1 2-nitroacetophenone 
• 1074-12-0 phenylglyoxal hydrate 
• 1816-88-2 2-azido-1-phenylethan-1-one 
• 14677-24-8 3-Morpholinoacrylophenon 
• 2461-80-5 diphenacyl sulfide 
• 1075-06-5 2,2-dihydroxy-1-phenyl-ethanone 
• 779-53-3 4-morpholinylacetophenone 

Downstream Products

• 143634-16-6 1-Morpholino-2-phenyl-1,2-ethanedithione 
• 611-73-4 Benzoylformic acid 
• 40991-78-4 4-(phenylglyoxylyl)morpholine 

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.

Unravelling the allosteric targeting of phgdh at the act-binding domain with a photoactivatable diazirine probe and mass spectrometry experiments

The serine biosynthetic pathway is a key element contributing to tumor proliferation. In recent years, targeting of phosphoglycerate dehydrogenase (PHGDH), the first enzyme of this pathway, intensified and revealed to be a promising strategy to develop ne

Desulfurizing agent for thioamides

Thioamides treated with thionyl chloride in an ionic liquid were successfully converted into amides.

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.

Alpha-ketothioamide compound and synthesis method thereof

The invention provides an alpha-ketothioamide compound and a synthesis method thereof. The alpha-ketothioamide compound is obtained by mixing an alpha-azidoacetophenone compound, an amine compound, elemental sulfur and a solvent, reacting for 0.5-4 hours

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

α-Ketothioamide Derivatives: A Promising Tool to Interrogate Phosphoglycerate Dehydrogenase (PHGDH)

Given the putative role of PHGDH in cancer, development of inhibitors is required to explore its function. In this context, we established and validated a straightforward enzymatic assay suitable for high-throughput screening and we identified inhibitors with similar chemical scaffolds. Through a convergent pharmacophore approach, we synthesized α-ketothioamides that exhibit interesting in vitro PHGDH inhibition and encouraging cellular results. These novel probes may be used to understand the emerging biology of this metabolic target.

Synthesis of α-Keto Amides by a Pyrrolidine/TEMPO-Mediated Oxidation of α-Keto Amines

A mild procedure has been developed for the synthesis of α-keto amides by α-oxidation of the corresponding α-keto amines mediated by pyrrolidine and TEMPO. The method can also be applied to the synthesis of α-keto thioamides and α-keto amidines.