69097-20-7Relevant articles and documents
Synthesis and in vitro Biological Evaluation of Ferrocenyl Side-Chain-Functionalized Paclitaxel Derivatives
Pla?uk, Damian,Wieczorek, Anna,Ciszewski, Wojciech M.,Kowalczyk, Karolina,B?au?, Andrzej,Pawl?dzio, Sylwia,Makal, Anna,Eurtivong, Chatchakorn,Arabshahi, Homayon J.,Reynisson, Jóhannes,Hartinger, Christian G.,Rychlik, B?a?ej
, p. 1882 - 1892 (2017/11/10)
Taxanes, including paclitaxel, are widely used in cancer therapy. In an attempt to overcome some of the disadvantages entailed with taxane chemotherapy, we devised the synthesis of ferrocenyl-functionalized paclitaxel derivatives and studied their biological properties. The cytotoxic activity was measured with a panel of human cancer cell lines of various tissue origin, including multidrug-resistant lines. A structure–activity study of paclitaxel ferrocenylation revealed the N-benzoyl-ferrocenyl-substituted derivative to be the most cytotoxic. In contrast, substitution of the 3′-phenyl group of paclitaxel with a ferrocenyl moiety led to less potent antiproliferative compounds. However, these agents were able to overcome multidrug resistance, as they were virtually unrecognized by ABCB1, a major cellular exporter of taxanes. Interestingly, the redox properties of these ferrocenyl derivatives appear to play a less important role in their mode of action, as there was no correlation between intracellular redox activity and cytotoxicity/cell-cycle distribution. The antiproliferative activity of ferrocenyl taxanes strongly depends on the substitution position, and good tubulin polymerization inducers, as confirmed by molecular docking, were usually more cytotoxic, whereas compounds with stronger pro-oxidative properties exhibited lower antiproliferative activity.
Reactions of Trialkylsilyl Trifluoromethanesulfonates, VI. - Synthesis of 2-Heterosubstituted O-Alkyl-O-(trimethylsilyl)ketene Acetals and 2-(Trimethylsilyl)carboxylates
Oesterle, Thomas,Simchen, Gerhard
, p. 687 - 692 (2007/10/02)
Organooxy- and (alkylthio)ethanoic acid esters 2 are silylated by trimethylsilyl triflate (1) in the presence of triethylamine to yield mixtures of ketene acetals 3 and 2-(trimethylsilyl)ethanoates 4.The product distributions 3/4 are governed by the ester groups and the substituents in α position.Cyclic derivatives of 2-hydroxycarboxylic acids 7,9 are silylated by 1/triethylamine to give the ketene acetals 8,10.From N-protected glycine methyl esters 11,12 the ketene acetals 13,15 are obtained in the reaction with 1/triethylamine.
