Dapson in Heterocyclic Chemistry, Part II: Antimicrobial and Antitumor Activities of Some Novel Sulfone Biscompounds Containing Biologically Active Thioureido, Carbamothioate, Quinazoline, Imidazolidine, and Thiazole Moieties

Abstract

The reaction of 4,4′-diisothiocyanato-1,1-diphenylsulfone 2 with aromatic amines and phenol derivatives afforded the corresponding thioureio derivatives 3–9 , respectively. Also, the reaction of 2 with catechol gave the corresponding carbamothioate derivative 11. Quinazoline derivatives 14 and 15 were obtained in good yield via reaction of 2 with anthranlic acid derivatives. Imidazolidine biscompounds 16 and 17 were readily synthesized from the reaction of 2 with N-(4-substituted-phenyl)cyanothioformanilides. The structure of the products was confirmed from elemental analysis as well as spectral data. Most of the synthesized compounds showed remarkable antimicrobial activity compared with chloramphenicol and Grisofluvine as positive controls. Compound 6 was almost as active an antitumor agent as the reference drug Doxorubicin.

Keywords:

• Antimicrobial and antitumor agents
• biscompounds bearing thioureido
• quinazoline
• and imidazolidine

Notes

^a IC₅₀ > 100 μ g/mL is considered to be inactive.