23516-79-2

Usage

Uses

Novel trifluoroacetophenone derivatives as malonyl-CoA decarboxylase inhibitors.

InChI:InChI=1/C8H6F3NO/c9-8(10,11)7(13)5-1-3-6(12)4-2-5/h1-4H,12H2

Upstream product

• 2396-05-6 1-(4-(dimethylamino)phenyl)-2,2,2-trifluoroethanone 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 619-50-1 4-nitrobenzoic acid methyl ester 
• 144459-68-7 α,α-bis(trifluoromethyl)-4-nitrobenzylalkohol 
• 655-32-3 2,2,2-trifluoro-1-(4-fluorophenyl)ethanone 

Downstream Products

• 193154-07-3 4-(N,N-dioctylamino)-4'-trifluoroacetylazobenzene 
• 812640-39-4 1-(4-amino-3-iodophenyl)-2,2,2-trifluoroethanone 
• 932036-95-8 1,1-diisobutyl-3-(4-trifluoroacetyl-phenyl)-urea 
• 74696-68-7 N-(4-trifluoroacetyl-phenyl)-isobutyramide 
• 449804-45-9 2-phenoxy-N-(4-trifluoroacetyl-phenyl)-acetamide 
• 1142905-97-2 1-(4-amino-3,5-dibromo-phenyl)-2,2,2-trifluoro-ethanone 
• 1197031-11-0 N-(4-(trifluoroacetyl)phenyl)-3,5-dinitrobenzamide 

Relevant academic research and scientific papers

Synthesis of diaziridines and diazirines via resin-bound sulfonyl oximes

Diazirines are one of the most prominent functionalities in labeling experiments in vivo and in vitro because they allow photochemical generation of carbenes. The strategy presented herein describes the formation of diaziridines, being essential precursors in diazirine syntheses, using solid-supported procedures with immobilized sulfonyl oximes. The solid-supported building blocks have been shown to be valuable intermediates for CuAAC and amidation reactions, offering the possibility to build complex compounds with diverse functionalities.

Novel trifluoroacetophenone derivatives as malonyl-CoA decarboxylase inhibitors

A series of trifluoroacetophenone derivatives were prepared and evaluated as malonyl-CoA decarboxylase (MCD) inhibitors. Some of the 'reverse amide' analogs were found to be potent inhibitors of MCD enzyme activity. The trifluoroacetyl group may interact with the MCD active site as the hydrate in a similar fashion to the hexafluoroisopropanol analogs reported previously. Adding electron-withdrawing groups to the phenyl ring stabilizes the hydrated species and enhances this interaction.

Pyrimidines and uses thereof

The invention relates to pyrimidines and uses thereof, including to inhibit lysophosphatidic acid acyltransferase β (LPAAT-β) activity and/or proliferation of cells such as tumor-cells.

Cross-linked dendrimer hosts containing reporter groups for amine guests

The integration of a chromogenic reporter group into the recently reported (Zimmerman, S. C.; Wendland, M. S.; Rakow, N. A.; Zharov, I.; Suslick, K. S. Nature 2002, 418, 399-403) monomolecular imprinting approach is described. The resulting highly cross-linked, macromolecular hosts show rapid, selective, high affinity, two-point binding of straight-chain diamine guests. Over longer times, the hosts are more promiscuous, binding a broader range of diamines. A rigorous test of imprinting was performed wherein the cross-reactivities of two dendrimers derived from different templates are compared. The test reveals a guest-dependent kinetic binding effect masquerading as evidence of a highly selective two-point imprinting process. Copyright

Reactions of ring-substituted 1-phenyl-2,2,2-trifluoroethyl carbocations with nucleophilic reagents: A bridge between carbocations which follow the reactivity-selectivity "principle" and the N+ Scale

The effect of changing carbocation reactivity on nucleophile selectivity has been determined for the reactions of ring-substituted 1-phenyl-2,2,2-trifluoroethyl carbocations, XArCH(CF3)+, with amines, alcohols, and carboxylate ions. Rate constants, Ks, for the capture of XArCH(CF3)+ by 50/50 (v/v) trifluoroethanol/water range from 1 × 1010 s-1 for 4-MeArCH(CF3)+ to ≤200 s-1 for 4-Me2NArCH(CF3)+. βnuc = 0.29 was determined for the reaction of alkylamines with 4-Me2NArCH(CF3)+. βnuc for reaction of RCO2- decreases from 0.35 for 4-Me2NArCH(CF3)+ to 0.05 for 4-MeOArCH(CF3)+. This decrease is due, at least in part, to a Hammond effect on the location of the reaction transition state along the reaction coordinate. βnuc for reaction of alcohols decreases from 0.48 for 4-Me2NArCH(CF3)+ to 0.09 for 4-MeArCH(CF3)+. The plot of log (KEtOH/KTFE for capture of XArCH(CF3)+ by ethanol and trifluoroethanol against log ks has a shallow negative slope for the more stable XArCH(CF3)+, which steepens with destabilization of the carbocation. This change in slope is due, in part, to a change in the magnitude of the Hammond effect, which corresponds to a third-derivative structure-reactivity effect, p*yyy = ?pyy-?σ > 0. There is considerable overlap between the reactivities of the most unstable triarylmethyl carbocations and the most stable XArCH(CF3)+, and there are also marked similarities in the reactivity-selectivity behavior of these species in the region of this overlap. Models are considered to explain the spectrum of reactivity-selectivity behavior that is observed on moving from very unreactive to very reactive carbocations.

The reduction of aryl trifluoromethyl ketones by sodium borohydride. The hydride transfer process

The rates of reduction of 17 aryl trifluoromethyl ketones by sodium borohydride in 2-propanol have been measured.The rho (ρ) value is 3.12, excluding the 4-amino and 4-dimethylamino groups, which both lower the rate to a greater extent than their ? values predict.The close correspondence between substituent effects for hydride addition in the methyl and trifluoromethyl series (excluding the amino groups) suggests that normal substituent effects are to be expected for oxidation processes involving hydride removal in trifluoromethyl compounds.The present results are consistent with the oxidation of aryl trifluoromethyl carbi ols by permanganate taking place by hydrogen atom abstraction.The effect of substituents on the rate of reduction of the trifluoromethyl ketones is almost identical to that on the equilibrium constant for formation of the ketone hydrates.The application of the reactivity-selectivity principle to the reduction reaction is also considered.Reduction of the 4-ethyl compound has ΔH = 2.7 kcal mol-1 and ΔS = -38 cal deg-1 mol-1.