2368-64-1

Usage

InChI:InChI=1/C9H5F6NO/c10-8(11,12)5-3-1-2-4-6(5)16-7(17)9(13,14)15/h1-4H,(H,16,17)

Upstream product

• 407-25-0 trifluoroacetic anhydride 
• 88-17-5 2-(trifluoromethyl)benzenamine 
• 76-05-1 trifluoroacetic acid 
• 61984-67-6 2,2,2-trifluoro-N-[2-(trifluoromethyl)phenyl]ethanimidoyl chloride 
• 183266-61-7 1-(trifluoroacetyl)benzotriazole 

Downstream Products

• 65767-78-4 C₁₃H₁₆BF₆N₃O 
• 61984-67-6 2,2,2-trifluoro-N-[2-(trifluoromethyl)phenyl]ethanimidoyl chloride 
• 1228757-62-7 N-(2-trifluoromethylphenyl)-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) trifluoroacetimidate 
• 1228757-58-1 N-(2-trifluoromethylphenyl)-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl) trifluoroacetimidate 

Relevant academic research and scientific papers

Acetanilide and bromoacetyl-lysine derivatives as activators for human histone deacetylase 8

In the current study, seven compounds (i.e. 1–7) were found to be novel activators for the Nε-acetyl-lysine deacetylation reaction catalyzed by human histone deacetylase 8 (HDAC8). When assessed with the commercially available HDAC8 peptide substrate Fluor-de-Lys-HDAC8 that harbors the unnatural 7-amino-4-methylcoumarin (AMC) residue immediately C-terminal to the Nε-acetyl-lysine residue to be deacetylated, our compounds exhibited comparable activation potency to that of TM-2-51, the strongest HDAC8 activator reported in the current literature. However, when assessed with an AMC-less peptide substrate derived from the native HDAC8 non-histone substrate protein Zinc finger protein ZNF318, while our compounds were all found to be able to activate HDAC8 deacetylation reaction, TM-2-51 was found not to be able to. Our compounds also seemed to be largely selective for HDAC8 over other classical HDACs. Moreover, treatment with the strongest activator among our compounds (i.e. 7) was found to decrease the KM of the above AMC-less HDAC8 substrate, while nearly maintaining the kcat of the HDAC8-catalyzed deacetylation on this substrate.

One-pot synthesis of novel (2R,4S)-N-aryl-4-hydroxy-1-(2,2,2-trifluoroacetyl) pyrrolidine-2-carboxamides via TiO 2 -NPs and Pd(PPh3)2Cl2 catalysts and investigation of their biological activities

Abstract: A new class of (2R,4S)-N-aryl-4-hydroxy-1-(2,2,2-trifluoroacetyl)pyrrolidine-2-carboxamide compounds was synthesized by a facile one-pot reaction of trans-4-hydroxy proline and trifluoroacetimidoyl chlorides in the presence of TiO 2-n

Trapped in misbelief for almost 40 years: Selective synthesis of the four stereoisomers of mefloquine

Here we report the synthesis of all four stereoisomers of mefloquine. Mefloquine (Lariam) is an important anti-malaria drug that is applied as a racemate of the erythro form. However, the (-)-isomer induces psychosis, while the (+)-enantiomer does not have this undesired side effect. There are six syntheses of which five lead to the wrong enantiomer without the authors of these syntheses noting that they had synthesized the wrong compound. At the same time physical chemistry investigations had assigned the absolute configuration correctly and the last enantioselective synthesis that took these results into account delivered the correct absolute configuration. Since various synthetic approaches failed to provide the correct stereoisomers in previous syntheses, we submit here a synthetic approach with a domino Sonogashira-6π- electrocyclisation as key step that confirmed synthetically the correct absolute configuration of all four isomers. Five to four: A total synthesis that yields all four stereoisomers of the important antimalarial drug mefloquine (Lariam) has been developed. This five-step approach with a domino Sonogashira-6π- electrocyclisation as key step has confirmed synthetically the correct absolute configuration of all four isomers (see scheme).

N-aryl-O-glycosyl haloacetimidates as glycosyl donors

Reaction of 1-O-unprotected tetra-O-acetyl- and tetra-O-benzyl- glucopyranose with N-aryl haloacetimidoyl chlorides in the presence of sodium hydride and 15-crown-5 afforded N-aryl-O-glucopyranosyl haloacetimidates. Mainly the β-anomers were obtained in this anomeric O-acylation-type reaction. The glycosyl donor properties of these haloacetimidates were investigated with 6-O- and 4-O-unprotected glucopyranosides as acceptors. The results were compared with those obtained with the corresponding O-glucopyranosyl trichloroacetimidates as glycosyl donors and the same acceptors. It was found that N-(2-chloro-6-methylphenyl)-O-glucopyranosyl trifluoroacetimidates (16Ad, 16Bd) exhibit glycosyl donor properties closely related to those of the corresponding N-unsubstituted O-glucopyranosyl trichloroacetimidates (12A, 12B). Copyright Taylor & Francis Group, LLC.