Synthesis,Voltammetric and Analytical Applications of Some Fluorine Substituted Spirosteroidalthiazolidin‐4‐one Derivatives of Sulfa Drugs

A new 5‐arylidene‐4‐oxo‐(sulfonamoyl phenyl)‐spiro[thiazolidinone‐2,2′‐steroids] series (7–10) was prepared by condensation of sulfanilamide, sulfapyridine and sulfadiazine sulfa drugs with testosterone, epiandrosterone and progesterone steroids, respectively. The resultant imino derivatives 1–3 upon cycloaddition with thioacetic acid in dry 1,4‐dioxane afforded 3‐sulfo‐namoylphenylspiro[4‐oxo‐thiazolidin‐2,2′steroids] (4–6). The latter compounds (4–6) upon condensation with p‐fluorobenzaldehyde in ethanol‐piperidine yielded the corresponding 4‐fluoroarylidene derivatives 7, 8 & 9, respectively. All the newly synthesized compounds were confirmed by UV, IR, ¹H NMR, ¹³C NMR, mass spectral data, elemental analysis and molecular weight determination. In vitro antimicrobial screening of some of the synthesized compounds showed good antimicrobial activities towards some pathogenic Gram‐positive, Gram‐negative bacteria and fungi vs. piperacillin and mycostatine antibiotics as standard antibacterial and antifungal agents, respectively. The voltammetric behavior of two newly spirothiazolidinone steroids ( 2a & 5a ) was critically studied. Compound 5a physically immobilized polyurethane foam solid sorbent was successfully used for removal and/or separation of bismuth(III) from water.