Khyluk D. Synthesis, transformation and biological activity of 2,3-diaryl(heteryl) 4-thiazolidones.

The object – reactions of three-component cyclocondensation, thionation, alkaline hydrolysis, Knyovenagel; the purpose – synthesis of 2,3-diaryl (hetero) -4-thiazolidinones and their 5-arylidene derivatives for the search of highly active and low-toxic compounds as potential drugs; methods – organic synthesis, NMR spectroscopy, chromatographic mass spectrometry, elemental analysis, X-ray diffraction (PCA) analysis, pharmacological screening, COMPARE analysis, molecular docking; results – as a result of the three-component one-pot interaction of amines, aldehydes and thioglycolic acid, a series of 2,3-diaryl-4-thiazolidinones was synthesized, the use of cyclohexanone or isatin as an oxocompounds leads to the obtaining of 2-spiro-substituted 4-thiazolidinones, namely 1-thia-4-azaspiro[4.5]decane-3-ones and spiro[3H-indole-3,2'-thiazolidine]2,4'(1H)-diones. 2,3-disubstituted 4-thiazolidinones readily react with P2S5 or Lawesson's reagent yielding corresponding 4-thioxo derivatives. For the first time, a series of 5-arylidene derivatives of pre-synthesized 2,3-disubstituted 4-thiazolidinones and 4-thiazolidinediones was obtained using a modified Knoevenagel reaction (medium 2-propanol, catalyst potassium tert-butylate). For the first time, a method for the synthesis of 5-arylidene-2,3-disubstituted-4-thiazolidinones is proposed, based on the use of 3-aryl-2-mercaptoacrylic acids in the ternary one-pot cyclic condensation with amines and aldehydes. Purposeful synthesis of 68 heterocyclic compounds was performed, among which 2 substances with high antitumor activity, 1 compound with antitrypanosomal activity and 7 compounds with selective antiviral effect and low toxicity were identified for the first time; introduced – into educational and scientific processes of the departments of pharmaceutical direction of Zaporizhzhia State Medical University and the National University of Pharmacy; direction – pharmacy.