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-oxothiazolidin- 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, H-1 NMR, C-13 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.