Synthesis of 1-aroyl(1-arylsulfonyl)-4-bis(trifluoromethyl)alkyl semicarbazides as potential physiologically active compounds

1,1-Bis(trifluoromethyl)alkyl isocyanates obtained from perfluoroisobutene (PFIB) react with aroyl(arylsulfonyl)hydrazines. Twenty eight prospective biologically active polyfluorinated 1,4-substituted semicarbazides were synthesized. The structure of each new product was confirmed by analytical and spectroscopic methods. The Lipinski's and Gelovani's parameters were then calculated. Two adjustments to the Lipinski rules of five are suggested for fluorinated drug candidates.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► 1,1-Bis(trifluoromethyl)alkyl isocyanates obtained from PFIB react with hydrazides. ► 28 prospective bioactive polyfluorinated 1,4-substituted semicarbazides were synthesized. ► The Lipinski's and Gelovani's parameters were calculated. ► 2 Adjustments to the Lipinski rules are suggested for fluorinated drug candidates.