Synthesis of some novel nitrogen-containing 5α-steroids based on tigogenin

A number of nitrogen-containing compounds were obtained using a condensation reaction catalyzed by acetic acid to investigate structure-chemical reactivity and structure-biological activity relationships in the search for potential biologically active steroids within ketones of the 5α-pregnane and 5α-androstane series. Novel steroidal hydrazones were synthesized from 5α-pregnan-3β-ol-20-one and 5α-pregna-9(11),16-dien-3α-ol-20-one, which, in turn, were obtained by a multistep transformation of 3β-acetoxy-5α-pregn-16-en-20-one. All of the starting steroid ketones were synthesized on the basis of a convenient domestic raw material – tigogenin, isolated from the Yucca gloriosa plant introduced in Georgia. Acetic acid catalyzed condensation reaction was carried out in ethanol using various reagents with pharmacophoric features – arylhydrazides, arylhydrazines, hydroxylamine, and semicarbazide. The structure of the newly obtained steroids was confirmed by1 H,13 C NMR, mass spectra and investigation of their biological activity is in process. The cytotoxic and antiviral activity of the previously synthesized steroid oximes, amines and hydrazones was assessed