TY  - JOUR
Y1  - 2015///
VL  - 98
ID  - publicatio6926
TI  - Synthesis of novel 17-(5?-iodo)triazolyl-3-methoxyestrane epimers via Cu(I)-catalyzed azide-alkyne cycloadditon, and an evaluation of their cytotoxic activity in vitro
A1  -  Schneider Gyula
A1  -  Görbe Tamás Ferenc
A1  -  Mernyák Erzsébet
A1  -  Wölfling János
A1  -  Holczbauer Tamás
A1  -  Czugler Mátyás
A1  -  Sohár Pál
A1  -  Minorics Renáta
A1  -  Zupkó István
N1  - FELTÖLT?: Zupkó István - zupko@pharm.u-szeged.hu
JF  - STEROIDS
N2  - Abstract The regioselective Cu(I)-catalyzed 1,3-dipolar cycloaddition of 3-methoxyestrane 17?- and 17?-azide epimers (3 and 5) with different terminal alkynes afforded novel 1,4-substituted triazolyl derivatives (8a-c and 10a-c). If the Ph3P in the classical CuAAC process was repleaced by Et3N, the formation of small quantities of 5-iodotriazoles (9a-c and 11a-c) was observed. For the preparation of 5-iodo-1,2,3-triazoles (9a-c and 11a-c), an improved method was developed, directly from steroidal azides and terminal alkynes, in reactions mediated by CuI and ICl as iodinating agents. The antiproliferative activities of the structurally related triazoles were determined in vitro with the microculture tetrazolium assay on six malignant human cell lines of gynecological origin (HeLa, A2780, MCF7, MB-231, MB-361 and T47D). X-ray analysis revealed the presence of the iodo substituent on the 1,2,3-triazole ring.
SP  - 153
UR  - http://publicatio.bibl.u-szeged.hu/6926/
SN  - 0039-128X
EP  - 165
AV  - restricted
ER  -