One of the main goals of modern medicine is to find appropriate medicines for hormone-dependent diseases. These compounds act as agonists and antagonists of naturally occurring hormones. Some structurally modified natural estrogens have already found their application in the treatment of estrogen-dependent diseases. The introduction of a heteroatom or heterocyclic ring into the steroid nucleus significantly affects its pharmacological and pharmacokinetic properties. Namely, the pyridine ring is an important structural characteristic of molecules used for therapeutic purposes. Herein we report two new and one previously synthesized pyridine-containing steroid derivatives. Starting from estrone and its C3 analogs, we have synthesized 17- (pyridin-2-yl) derivates of estra-1,3,5(10)-triene. In silico ADMET properties were examined for synthesized compounds by using two online tools. SwissADME was used for bioavailability prediction, while in silico toxicology tests were performed with the ProTox-II virtual lab. Also, virtual screening was performed on the SwissTargetPrediction website in order to estimate the most probable macromolecular targets of obtained compounds and thus their biological activity.