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

Abstract

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, 1 H NMR, 13 C 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.

Synthesis of Novel Fluorine Compounds Substituted-4-thiazolidinones Derived from Rhodanine Drug as Highly Bioactive Probes

“…Introduction of fluorine atoms to heterocyclic nitrogen systems often improves their physical with chemical advantages and enhances their biological activity [ 17 - 20 ]. Based on these obser-vations, the present work describes the development of new fluorine compound substituted rhodanine derivatives which may enhance the biological effects, as cellobiase produced by fungi as well as CDK2 inhibitors for tumor cell (DNA damage).…”

Synthesis of Some New Thioethers and 4-Thiazolidinones Bearing 3-(Pyridine-4'-yl)-1,2,4-Triazino[5,6-<i>b</i>]Indole Moiety as Antifungal Agents

“…C,61.24;H,3.40;N,15.90;Cl,13.42;S,6.04% for C 27 H 18 N 6 Cl 2 S (529). Found C,61.18;H,3.25;N,15.81;S,5.89;Cl,13.38%.…”

“…4-Thiazolidinone derivatives exhibited a wide range of biological activity especially as antifungal agents [11] [13], also, thioethers bearing a heterocyclic nitrogen systems used as anticancer, and anti-HIV probes [10]. Besides, the 1,2,4-triazino [5.6-b] indole, showed various biological activities [4]…”

Synthesis of Novel 4-Thiazolidinone and Bis-Thiazalidin-4-One Derivatives Derived from 4-Amino-Antipyrine and Evaluated as Inhibition of Purine Metabolism Enzymes by Bacteria

“…Recently, 4-thiazolidinones derivatives exhibited a wide spectrum of biological medicinal and pharmacological properties such as antibacterial, antioxidant, and hypoglycemic activity [2]. Most of 4-thiazolidinones synthesized exhibited antifungal and antibacterial ac-International Journal of Organic Chemistry tivity [3] [4] [5]. 4-Amino-antipyrine showed various important properties as an anti-inflammatory [6], antimicrobial [7] and as an inhibitor of mild steel corrosion in HCl solution [8].…”