586333-28-0Relevant articles and documents
Mild and Regioselective Synthesis of 3-CF3-Pyrazoles by the AgOTf-Catalysed Reaction of CF3-Ynones with Hydrazines
Topchiy, Maxim A.,Zharkova, Daria A.,Asachenko, Andrey F.,Muzalevskiy, Vasiliy M.,Chertkov, Vyacheslav A.,Nenajdenko, Valentine G.,Nechaev, Mikhail S.
supporting information, p. 3750 - 3755 (2018/07/31)
Gold- and silver-catalysed reactions of trifluoromethylated ynones with aryl (alkyl) hydrazines were investigated. The use of (THD-Dipp)AuOTf and AgOTf resulted in quick heterocyclization reactions to selectively give 3-CF3-pyrazoles. AgOTf was found to be the catalyst of choice, and various 3-CF3-pyrazoles were formed in up to 99 % isolated yield with high regioselectivity. The reaction has a broad scope: 3-CF3-pyrazoles with alkyl and aryl substituents as well as different functional groups can be prepared by this approach. The known pyrazole drugs Celebrex and SC-560 were efficiently prepared to demonstrate the utility of the method. Mechanistic investigations revealed that the reaction involves the formation of a hemiaminal as a key intermediate.
Synthesis of 3-trifluoromethylpyrazoles via trifluoromethylation/ cyclization of α,β-alkynic hydrazones using a hypervalent iodine reagent
Ji, Guojing,Wang, Xi,Zhang, Songnan,Xu, Yan,Ye, Yuxuan,Li, Ming,Zhang, Yan,Wang, Jianbo
supporting information, p. 4361 - 4363 (2014/04/17)
A mild and efficient method for the synthesis of 3-trifluoromethylpyrazoles has been established via trifluoromethylation/cyclization of α,β-alkynic hydrazones using a hypervalent iodine reagent under transition-metal-free conditions.
Design, synthesis, and biological evaluation of substituted hydrazone and pyrazole derivatives as selective COX-2 inhibitors: Molecular docking study
El-Sayed, Magda A.-A.,Abdel-Aziz, Naglaa I.,Abdel-Aziz, Alaa A.-M.,El-Azab, Adel S.,Asiri, Yousif A.,Eltahir, Kamal E.H.
, p. 3416 - 3424 (2011/07/08)
New arylhydrazone derivatives and a series of 1,5-diphenyl pyrazoles were designed and synthesized from 1-(4-chlorophenyl)-4,4,4-trifuorobutane-1,3-dione 1. The newly synthesized compounds were investigated in vivo for their anti-inflammatory activities using carrageenan-induced rat paw oedema model. Moreover, they were tested for their inhibitory activity against ovine COX-1 and COX-2 using an in vitro cyclooxygenase (COX) inhibition assay. Some of the new compounds (2f, 6a and 6d) showed a reasonable in vitro COX-2 inhibitory activity, with IC50 value of 0.45 μM and selectivity index of 111.1. A virtual screening was carried out through docking the designed compounds into the COX-2 binding site to predict if these compounds have analogous binding mode to the COX-2 inhibitors. Docking study of the synthesized compounds 2f, 6a and 6d into the active site of COX-2 revealed a similar binding mode to SC-558, a selective COX-2 inhibitor.
