Syntheses of Some Novel Imidazolidinethiones and Condensed Imidazoles Containing Arylazo Moieties Starting from Cyanothioformamides.

Synthesis and Biological Evaluation of Bis‐Imidazolidineiminothiones: A Comparative Study

“…These could be stored at room temperature for prolonged periods of time without showing any signs of instability as corroborated by NMR analysis or developing odors indicative of decomposition. Encouraged by the precedent broad spectrum bioactivity of imidazolidineiminothiones and the preliminary promising biological activity of the corresponding bis‐imidazolidineiminothiones reported earlier , herein we investigate bis‐iminothiones 6a – g as potential antitumor, antibacterial, antifungal, and antiviral agents that contain the pharmacophore iminothione units separated by a flexible n ‐hexane linker between the N ‐(3) atoms and contain variously substituted phenyl rings at N ‐(1). Therefore, a comparative structure‐activity study should uncover the effect exerted by the N ‐(1) substituents and highlight the most appropriate group for optimum bioactivity which will ultimately enable structural optimization and the design of highly active bis‐imidazolidineiminothione heterocycles.…”

“…Bis‐imidazolidineiminothiones ( 4 ) are virtually unknown and remain unexplored in many respects. It is noted that literature search returned no references detailing the preparation and bioactivity of such species besides seven bis‐imidazolidineiminothione compounds reported earlier by our group . Interestingly, cytotoxic activity studies against various carcinoma cell lines (brain tumor cell line, human hepatocellular carcinoma cell line, human breast adenocarcinoma cell line, human epithelial carcinoma cell line, and colon carcinoma cell line) underscored the effectiveness and superiority of bis‐imidazolidineiminothiones as they were markedly more active in the 1–5 µg/mL range relative to imidazolidineiminothiones and related derivatives as indicated by the median inhibition concentration (IC 50 ) values .…”

“…N ‐Arylcyanothioformanilides are ambident nucleophiles and may react via the sulfur or nitrogen atom , with the nitrile group serving as an electrophilic tether that may participate in subsequent transformations. These inherent features have been employed to design several “one‐pot” annulation reactions to produce various heterocyclic cores .…”