137550-67-5Relevant academic research and scientific papers
An SAR study of hydroxy-trifluoromethylpyrazolines as inhibitors of Orai1-mediated store operated Ca2+ entry in MDA-MB-231 breast cancer cells using a convenient Fluorescence Imaging Plate Reader assay
Stevenson, Ralph J.,Azimi, Iman,Flanagan, Jack U.,Inserra, Marco,Vetter, Irina,Monteith, Gregory R.,Denny, William A.
, p. 3406 - 3413 (2018)
The proteins Orai1 and STIM1 control store-operated Ca2+ entry (SOCE) into cells. SOCE is important for migration, invasion and metastasis of MDA-MB-231 human triple negative breast cancer (TNBC) cells and has been proposed as a target for cancer drug discovery. Two hit compounds from a medium throughput screen, displayed encouraging inhibition of SOCE in MDA-MB-231 cells, as measured by a Fluorescence Imaging Plate Reader (FLIPR) Ca2+ assay. Following NMR spectroscopic analysis of these hits and reassignment of their structures as 5-hydroxy-5-trifluoromethylpyrazolines, a series of analogues was prepared via thermal condensation reactions between substituted acylhydrazones and trifluoromethyl 1,3-dicarbonyl arenes. Structure-activity relationship (SAR) studies showed that small lipophilic substituents at the 2- and 3-positions of the RHS and 2-, 3- and 4-postions of the LHS terminal benzene rings improved activity, resulting in a novel class of potent and selective inhibitors of SOCE.
Molecular structure of 3-trifluoroacetamidobenzoyltrifluoroacetone enol form
Semenov,Zolotareva,Baranov
, p. 471 - 475 (2013)
3-Trifluoroacetamidobenzoyltrifluoroacetone formed in the reaction of 3-aminoacetophenone with an excess of methyl trifluoroacetate crystallizes in the cis-enol form with a hydroxy group located at the carbon atom bound with the trifluoromethyl substituent. Analysis of geometric characteristics indicate the presence of both intramolecular hydrogen bond in the enol fragment and intermolecular H.O contacts in the crystal of the compound.
Synthesis of 3-trifluoroacetamidobenzoyltrifluoroacetone and its luminescent europium complexes
Semenov,Zolotareva,Cherkasov
experimental part, p. 874 - 879 (2012/09/22)
Reaction of 3-aminoacetophenone with excess of methyl trifluoroacetate proceeds in two stages and leads to the formation of 3- trifluoroacetamidobenzoyltrifluoroacetone 3-CF3C(O)NHC 6H4C(O)CH2C(O)CF3
