Syntheses and antiproliferative effects of d-homo- and d-secoestrones

Comparative investigation of thein vitroinhibitory potencies of 13-epimeric estrones and D-secoestrones towards 17β-hydroxysteroid dehydrogenase type 1

“…Structural formulae of the test compounds (1)(2)(3)(4)(5)(6) 51,52 . Our potential anticancer agents were designed on the hormonally inactive D-seco-and/or 13a-estrone core.…”

“…Our potential anticancer agents were designed on the hormonally inactive D-seco-and/or 13a-estrone core. 3-Benzyloxy-D-secoestrone alcohol (3b), the first D-secoestrone in the literature, displays substantial in vitro antiproliferative effects against a number of human reproductive cancer cell lines with good tumour selectivity 51 . The debenzylated secoalcohol (3a) containing a 3-phenolic group did not inhibit tumour cell growth markedly.…”

Synthesis andin vitropharmacological evaluation ofN-[(1-benzyl-1,2,3-triazol-4-yl)methyl]-carboxamides ond-secoestrone scaffolds

“…The literature reveals that the homologization or opening of ring D or inversion of the configuration at C-13 of the estrane skeleton may lead to the complete loss of estrogenic activity [7][8][9] . We recently reported that 3-benzyloxy-D-secoestrone alcohols and oximes display high in vitro antiproliferative potential against a number of cancer cell lines, with IC 50 values in the low micromolar or submicromolar range 10,11 . The most potent compounds were found to induce apoptosis via the enhancement of tubulin polymerization or to cause disturbance in a cell cycle.…”

“…To diversify the structure, starting compounds bearing different protecting groups at C-3 were used. D-Secoestrone carboxylic acids are readily available in both the 13a-and the 13b-estrone series 10,[13][14][15] . We therefore set out to build additional structural elements, such as a triazole moiety, onto the carboxylic acid scaffolds, in order to obtain compounds with enhanced antiproliferative properties 10 .…”

Characterization of antiproliferative activities of triazolyl-steroid derivatives

“…Non-toxic concentrations of digitoxin and digoxin inhibit growth and induce apoptosis in different human malignant cell lines, whereas highly proliferating normal cells are not affected. Although these compounds have no use as anticancer agents because of the cardiac side effects, the structure of these compounds can be used for the development of novel anticancer agents (Mijatovic and Kiss, 2013 (Minorics et al, 2012, Berényi et al, 2013, Kovács et al, 2014, Mernyák et al, 2014 et al, 1986, Alvarez et al, 1994, Genin et al, 2000, Zhou and Wang, 2012, Sahu et al, 2013. The introduction of a triazole ring at position 3 of the natural triterpene betulinic acid resulted in a set of compounds with considerable antiproliferative potency and proapoptotic capacity (Majeed et al, 2013).…”