%0 Journal Article
%@ 0039-128X
%A  Mernyák Erzsébet
%A  Huber Judit
%A  Szabó Johanna
%A  Schneider Gyula
%A  Hetényi Anasztázia
%A  Márk László
%A  Maász Gábor
%A  Berényi Ágnes
%A  Kovács Ida Jusztina
%A  Minorics Renáta
%A  Zupkó István
%A  Wölfling János
%A Gyógyszerhatástani és Biofarmáciai Intézet SZTE / GYTK GYBI [2000-],
%A Szentágothai János Kutatóközpont PTE SZKK,
%A Biokémiai és Orvosi Kémiai Intézet PTE / ÁOK BOKI,
%A Szerves Kémiai Tanszék SZTE / TTIK / KTCS SZT [2007-2015],
%A Orvosi Vegytani Intézet SZTE / SZAOK OVI [2000-],
%D 2013
%F publicatio:28285
%J STEROIDS
%N 10
%P 1021-1028
%T Cycloaddition of Steroidal Cyclic Nitrones to C=N Dipolarophiles: Stereoselective Synthesis and Antiproliferative Effects of Oxadiazolidinones in the Estrone Series
%U http://publicatio.bibl.u-szeged.hu/28285/
%V 78
%X Cyclic nitrones of estrone 3-methyl or 3-benzyl ether were reacted with phenyl isocyanate or nonsubstituted phenyl isocyanates as reactive C=N dipolarophiles, yielding condensed homosteroidal oxadiazolidinones. These dipolar cycloadditions were carried out under conventional heating or microwave irradiation. The chemo- and stereoselectivities of the reactions and the effects of the aromatic substituents on the reaction rates and yields were investigated and compared. The structures of the new products were determined by NMR (one- and two-dimensional) and MALDI-MS techniques, with C70 fullerenes as matrix in the latter case. The antiproliferative properties of the synthetized compounds were determined on a panel of human adherent cell lines (HeLa, MCF7, A2780 and A431) by means of MTT assays. Some of them exhibited activities comparable to that of the reference agent cisplatin. Flow cytometry indicated that one of the most potent agents (11a) resulted in a cell cycle blockade.
%Z Funding Agency and Grant Number: Hungarian Scientific Research Fund [OTKA K101659]; [TAMOP-4.2.2./B-10/1-2010-0012]\n Funding text: The authors thank the Hungarian Scientific Research Fund (OTKA K101659) and TAMOP-4.2.2./B-10/1-2010-0012 for financial support. Special thanks should be given to Reinhard Machinek (University of Gottingen) for his useful recommendations.\n CAplus AN 2013:1291258; MEDLINE PMID: 23831783 (Journal; Article; Research Support, Non-U.S. Gov't);