5460-83-3Relevant articles and documents
Synthesis of diblock copolymers consisting of hyaluronan and poly(2-ethyl-2-oxazoline)
Yang, Yali,Kataoka, Kazunori,Winnik, Francoise M.
, p. 2043 - 2046 (2005)
The preparation of biomimetic diblock copolymers consisting of two hydrophilic units which include a nonionic block (PEtOz) and an anionic block (HA) was discussed. The amine-terminated poly(2-ethtyl-2-oxazolines) (NH 2PEtOz) was prepared using
Insights into the Pummerer synthesis of oxazolines
Becerra-Cely, Laura,Rueda-Espinosa, Juan,Ojeda-Porras, Andrea,Gamba-Sánchez, Diego
, p. 8474 - 8485 (2016/09/28)
A rapid and simple method to access unnatural 2-substituted 5-thio oxazolines has been developed. This methodology is based on a Pummerer reaction followed by an intramolecular nucleophilic substitution, which changes the paradigm for the normal use of a base in Pummerer chemistry. We also provide a useful two-step method for the synthesis of the starting material and a mechanistic proposal based on experimental observations, which contests the previously proposed reaction pathway. The reaction proved to be general, and different substituents, such as alkyl, aryl, alkenyl and functionalized groups, can be used without a significant decrease in efficiency.
Synthesis, cytotoxicity, and insight into the mode of action of Re(CO) 3 thymidine complexes
Bartholomae, Mark D.,Vortherms, Anthony R.,Hillier, Shawn,Ploier, Birgit,Joyal, John,Babich, John,Doyle, Robert P.,Zubieta, Jon
experimental part, p. 1513 - 1529 (2011/11/29)
Nucleoside analogues are extensively used in the treatment of cancer and viral diseases. The antiproliferative properties of organorhenium(I) complexes, however, have been scarcely explored to date. Herein we present the syntheses, characterization, and in vitro evaluation of ReI(CO)3 core complexes of thymidine and uridine. For the binding of the Re I(CO)3 core, a tridentate dipicolylamine metal chelate was introduced at positions C5′, C2′, N3, and C5 with spacers of various lengths. The corresponding organometallic thymidine complexes were fully characterized by IR and NMR spectroscopy and mass spectrometry. Their cytotoxicity was assessed against the A549 lung carcinoma cell line. Toxicity is dependent on the site and mode of conjugation as well as on the nature and the length of the tether. Moderate toxicity was observed for conjugates carrying the rhenium moiety at position C5′ or N3 (IC50=124-160 μm). No toxicity was observed for complexes modified at C2′ or C5. Complex 53, with a dodecylene spacer at C5′, exhibits remarkable toxicity and is more potent than cisplatin, with an IC50 value of 6.0 μm. To the best of our knowledge, this is the first report of the antiproliferative properties of [M(CO)3]+1-nucleoside conjugates. In competitive inhibition experiments with A549 cell lysates and purified recombinant human thymidine kinase 1 (hTK-1), enzyme inhibition was observed for complexes modified at either N3 or C5′, but our results suggest that the toxicity cannot be attributed solely to interaction with hTK-1.
