655228-33-4Relevant academic research and scientific papers
Design, synthesis, and bioactivity of putative tubulin ligands with adamantane core
Zefirova, Olga N.,Nurieva, Evgeniya V.,Lemcke, Heiko,Ivanov, Andrei A.,Shishov, Dmitrii V.,Weiss, Dieter G.,Kuznetsov, Sergei A.,Zefirov, Nikolay S.
supporting information; experimental part, p. 5091 - 5094 (2009/06/18)
Several adamantane-based taxol mimetics were synthesized and found to be cytotoxic at micromolar concentrations and to cause tubulin aggregation. The extent of the aggregation is maximal for N-benzoyl-(2R,3S)-phenylisoseryloxyadamantane (5) and is very sensitive to the structural modifications. A hybrid compound (15), combining adamantane-based taxol mimetic with colchicine was synthesized and found to possess both microtubule depolymerizing and microtubule bundling activities in A549 human lung carcinoma cells.
O-N Intramolecular acyl migration strategy in water-soluble prodrugs of taxoids
Skwarczynski, Mariusz,Sohma, Youhei,Kimura, Maiko,Hayashi, Yoshio,Kimura, Tooru,Kiso, Yoshiaki
, p. 4441 - 4444 (2007/10/03)
We synthesized a highly water-soluble canadensol prodrug 6 that formed canadensol 3 by a simple pH-dependent chemical mechanism via the O-N intramolecular acyl migration of the isobutyryl group. This prodrug, a 2′-O-isobutyryl isoform of 3, has no additio
