An Efficient Synthesis of New 7-Trifluoromethyl-2,5-disubstituted Pyrazolo 1,5-a pyrimidines

International audienceA novel two-step synthesis of trifluoromethylated 3,5-disubstituted pyrazolo[1,5- a ]pyrimidines is reported from 3-aminopyrazoles and ethyl 4,4,4-trifluorobut-2-ynoate. The synthetic route begins with the one-pot synthesis of 7-trifluoromethylated pyrazolo[1,5- a ]pyrimidin-5-ones by condensation of 3-aminopyrazoles with a fluorinated alkyne. The products obtained are used as building blocks to synthesize directly, with excellent yields via C-O bond activation, a library of new fluorinated 3,5-disubstituted pyrazolo[1,5- a ]pyrimidines of biological interest. This operation efficiently allows C-C, C-N and C-S bond formation

An efficient and simple one-pot synthesis of 2-perfluoroalkylated benzo[1,3]dioxole derivatives via double–Michael reaction of fluorinated alkynes

International audienceAn efficient, mild and very easy method for the synthesis of 2-fluoroalkylated 1,3-benzodioxole derivatives was developed through a double Michael-addition reaction on ethyl 4,4,4-trifluorobut-2-ynoate with corresponding catechols. The procedure does not require the use of expensive supplementary additives for the preparation of 2-fluoroalkylated benzo ketals

Efficient synthesis and preliminary biological evaluations of trifluoromethylated imidazo[1,2- a ]pyrimidines and benzimidazo[1,2- a ]pyrimidines

International audienceFluoromethylated imidazo[1,2-a]pyrimidines and benzimidazo[1,2-a]pyrimidines were synthesized through Michael addition/intramolecular cyclization reaction by condensation of 2-amino imidazole derivatives with ethyl 4,4,4-trifluorobut-2-ynoate and using C–O bond activation. The synthons thus obtained can be functionalized by forming new chemical bonds, including C–C, C–N and C–S, to provide easy access to a wide range of novel trifluoromethylated imidazo[1,2-a]pyrimidines and benzimidazo[1,2-a]pyrimidines in good to excellent yields. Preliminary biological evaluation revealed a number of derivatives displaying micromolar IC50 values against monoamine oxidase B and butyrylcholinesterase, two important targets in the field of neurodegenerative disorders

Synthèse de nouveaux dérivés du 9-hydroxy-parthénolide contenant un noyau -1,2,3-triazole substitué

National audienc

Synthesis and characterization of new pyrazolopyrimidine derivatives as hole transporting materials for hybrid solar cell application

International audienc

Three Component One-Pot Synthesis and Antiproliferative Activity of New [1,2,4]Triazolo[4,3-<i>a</i>]pyrimidines

A series of new [1,2,4]triazolo[4,3-a]pyrimidine derivatives was prepared using a one-pot three-component synthesis from 5-amino-1-phenyl-1H-1,2,4-triazoles, aromatic aldehydes and ethyl acetoacetate. The compound structures were confirmed by IR, 1H-NMR, 13C-NMR, HRMS and X-ray analyses. The biological activity of these compounds as antitumor agents was evaluated. Their antitumor activities against cancer cell lines (MDA-MB-231 and MCF-7) were tested by the MTT in vitro method. Among them, compounds 4c and 4j displayed the best antitumor activity with IC50 values of 17.83 μM and 19.73 μM against MDA-MB-231 and MCF-7 cell lines, respectively, compared to the Cisplatin reference

Synthetic modification of 9 alpha- and 9 beta-hydroxyparthenolide by Heck or acylation reactions and evaluation of cytotoxic activities

International audienceMotivated by the widely reported anticancer activity of parthenolides and their derivatives, a series of new substituted parthenolides was efficiently synthesized. Structural modifications were performed at the C-9 and C-13 positions of 9 alpha- and 9 beta-hydroxyparthenolide, which were isolated from the aerial parts of Anvillea radiata. Twenty-one derivatives were synthesized and evaluated for their in vitro cytotoxic activity against HS-683, SK-MEL-28, A549, and MCF-7 human cancer cell lines using the MTT colorimetric assay. Among the derivatives, seven exhibited excellent activity compared to 5-fluorouracil and etoposide against the four cell lines tested, with IC50 values ranging from 1.1 to 9.4 mu M. [GRAPHICS]