Author/Editor		Traj, Péter; Abdolkhaliq, Ali Hazhmat; Németh, Anett; Dajcs, Sámuel Trisztán; Tömösi, Ferenc; Lanišnik-Rižner, Tea; Zupkó, István; Mernyák, Erzsébet
Title		Transition metal-catalysed A-ring C-H activations and C(sp2)-C(sp2) couplings in the 13[alpha]-oestrone series and in vitro evaluation of antiproliferative properties
Type		članek
Vol. and No.		Letnik 36, št. 1
Publication year		2021
Volume		str. 895-902
ISSN		1475-6366 - Journal of enzyme inhibition and medicinal chemistry
Language		eng
Abstract		Facile syntheses of 3-O-carbamoyl, -sulfamoyl, or -pivaloyl derivatives of 13[alpha]-oestrone and its 17-deoxy counterpart have been carried out. Microwave-induced, Ni-catalysed Suzuki-Miyaura couplings of the newly synthesised phenol esters with phenylboronic acid afforded 3-deoxy-3-phenyl-13a-oestrone derivatives. The carbamate and pivalate esters proved to be suitable for regioselective arylations. 2-(4- Substituted) phenyl derivatives were synthesised via Pd-catalysed, microwave-assisted C-H activation reactions. An efficient, one-pot, tandem methodology was elaborated for the introduction of the carbamoyl or pivaloyl group followed by regioselective C-2-arylation and subsequent removal of the directing group. The antiproliferative properties of the novel 13a-oestrone derivatives were evaluated in vitro on five human adherent cancer cell lines of gynaecological origin. 3-Sulfamate derivatives displayed substantial cell growth inhibitory potential against certain cell lines. The newly identified antiproliferative compounds having hormonally inactive core might be promising candidates for the design of more active anticancer agents.
Keywords		reproduktivne celične linije antiproliferativno delovanje 13afa-estron reproductive cell lines antiproliferative action 13alpha-oestrone