779-53-3

Upstream product

• 110-91-8 morpholine 
• 70-11-1 α-bromoacetophenone 
• 50-00-0 formaldehyd 
• 100-52-7 benzaldehyde 
• 79409-16-8 2-diphenylphosphinoyl-2-morpholin-4-yl-1-phenyl-ethanol 
• 110380-87-5 4-(trans-3-phenyl-oxiranesulfonyl)-morpholine 
• 136132-07-5 3-(bromomethyl)-3-phenyl-1,2-dioxetane 
• 3282-32-4 2-diazo-acetophenone 
• 450-95-3 2-fluoroacetophenone 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 98-86-2 acetophenone 
• 4136-21-4 p-methoxybenzoylmethanol 

Downstream Products

• 13150-37-3 2-(N-morpholinyl)-1,1-diphenylethanol 
• 97295-29-9 phenyl 1-morpholino-2,2-dichlorovinyl ketone 
• 97315-06-5 (E)-3-Chloro-2-morpholin-4-yl-1,3-diphenyl-propenone 
• 5509-99-9 2-morpholino-1-phenyl-2-thioxoethanone 
• 4432-34-2 2-morpholino-1-phenylethanol 
• 40116-78-7 (R)-2-morpholino-1-phenylethanol 
• 87837-32-9 (S)-2-(morpholin-1-yl)-1-phenylethanol 
• 97295-30-2 3-chloro-1,3-diphenyl-1,2-propanedione 
• 110-91-8 morpholine 
• 1207202-15-0 C₁₉H₂₃N₃O₃S 
• 1248740-18-2 2-phenyl-3-morpholino-5-hydroxy-benzo[g]indole 
• 40991-78-4 4-(phenylglyoxylyl)morpholine 
• 98-86-2 acetophenone 
• 1468-28-6 4-benzoylmorpholine 

Relevant academic research and scientific papers

One pot synthesis of α-N-heteroaryl ketone derivatives from aryl ketones using aqueous NaICl2

A simple and efficient method for the synthesis of α-heteroaryl ketones from aryl ketones and amine using aqueous sodium dichloroiodate is established. This method is mild, operationally simple, has a short reaction time, and easy workup procedure to afford the corresponding α-N-heteroaryl ketone derivatives in moderate to good yield.

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.

Solvent-Free Synthesis of α-Amino Ketones from α-Hydroxyl Ketones via A Novel Tandem Reaction Sequence Based on Heyns Rearrangement

Heyns rearrangement have been famous for carbohydrate chemists for several decades. However, this reaction was underrated as a useful method for synthetic chemists due to preparative shortcomings. Herein we developed an efficient method for the synthesis of pharmaceutically important α-amino ketones from readily available α-hydroxy ketones and secondary amines through a tandem reaction sequence based on Heyns rearrangement. The reaction smoothly proceeded by using catalytic PTSA as catalyst without solvent. Primary and secondary α-hydroxy ketones were readily used and regioselectively afforded the correspondingly α-amino ketones with moderate yield.

Enabling nucleophilic substitution reactions of activated alkyl fluorides through hydrogen bonding

It was discovered that the presence of water as a cosolvent enables the reaction of activated alkyl fluorides for bimolecular nucleophilic substitution reactions. DFT calculations show that activation proceeds through stabilization of the transition structure by a stronger F···H 2O interaction and diminishing C-F bond elongation, and not simple transition state electrostatic stabilization. Overall, the findings put forward a distinct strategy for C-F bond activation through H-bonding.

Simplified heterocyclic analogues of fluoxetine inhibit inducible nitric oxide production in lipopolysaccharide-induced BV2 cells

A series of fluoxetine, where the N-methylamino group was replaced and then simplified, were synthesized and their inhibitory effect was tested for nitric oxide (NO) production and inducible NO synthase (iNOS) expression in lipopolysaccharide (LPS)-induced BV2 cells. Although the synthesized compounds generally revealed weaker activity or greater cytotoxicity than fluoxetine, compound 10a, in which the N-methylamino group in fluoxetine was replaced by morpholine, and the trifluoromethylphenyl ring was substituted with simple oxo group, suppressed NO production dose-dependently at 10, 20 and 40 μM concentrations with less cytotoxicity than fluoxetine, and inhibited iNOS mRNA and protein expression at the same concentrations in LPS-induced BV2 cells. The results suggested that the trifluoromethylphenyl ring moiety in fluoxetine is not necessary for the suppression of NO production and that 10a has the potential as a potent inhibitor of NO production.

Biomimetic transfer hydrogenation of 2-alkoxy- and 2-aryloxyketones with iron-porphyrin catalysts

In situ generated iron porphyrins are applied as homogeneous catalysts in the transfer hydrogenation of α-substituted ketones. Using 2-propanol as hydrogen donor various protected 1,2-hydroxyketones are reduced to the corresponding mono-substituted 1,2-di

Novel N,S-phenacyl protecting group and its application for peptide synthesis

The phenacyl group can be introduced onto amino and thio groups by N,S-alkylation reactions. Conversely, these groups are removed rapidly by employing magnesium in acetic acid. This protecting group was successfully applied to a short peptide synthesis of Boc-L-Cys-Gly-OMe. Georg Thieme Verlag Stuttgart.

Synthesis and Biological activity of kappa opioid receptor agonists. Part 2: Preparation of 3-aryl-2-pyridone analogues generated by solution- and solid-phase parallel synthesis methods

New analogues of the previously described 3-aryl pyridone KOR agonists have been synthesised by parallel synthetic methods, both in solution- and with solid-phase chemistry, making use of the well known and versatile Mitsunobu, Suzuki and Buchwald reactions. Opioid receptor binding data for the compounds produced is reported.

Indium tribromide: A highly effective catalyst for the addition of trimethylsilyl cyanide to α-hetero-substituted ketones

The catalytic addition of trimethylsilyl cyanide (TMSCN) to a large variety of hetero-substituted ketones promoted by anhydrous InBr3 has been studied. The low catalytic loading (0.1-1 mol%) and the mild experimental conditions required represe

Highly chemoselective α-diazo carbonyl insertion reactions into N-H and S-H bonds catalysed by [RuCl(η5-C5H5)(PPh3)2]

Complex [RuCl(η5-C5H5)(PPh3)2], in chloroform at 60 deg C, catalyses the chemoselective insertion of α-diazo carbonyl compounds into N-H and S-H bonds to afford α-keto-amines and α-keto-thioethers.