Synthesis, antifungal, antitumor and anti-inflammatory activities of some new 5-substituted arylimino-3-(2,4-diethoxyarylimino)-1,2,4-dithiazolidines

Abstract

5-Substituted arylimino-3-(2,4-diethoxyarylimino)-1,2,4-dithiazolidines 4a-e have been synthesized by oxidative debenzylation and cyclization with bromine in chloroform from the corresponding 1-substituedaryl-5-(2,4- diethoxyaryl)-2-5-benzyl-iso-2,4-dithiobiurets 3a-e or by the oxidation of corresponding 1-substituted aryl-5-(2,4-diethoxyaryl)-2,4-dithio-biurets 5a-e, obtained from 3 a-e by reductive debenzylation with hydrogen sulphide in a mixture of pyridine and triethylamine.1-Substituted aryl-5-(2,4-diethoxyaryl)-2- S-benzyl-iso-2,4-dithiobiurets 3a-e, in turn, are prepared by the condensation of 1-substituted aryl-2-S-benzylisocarbamides 2a-e with 2,4-diethoxyaryl- isothiocyanate. The title dithiazolidines have been characterized by their element analyses, IR, 1H NMR, 13C NMR and mass spectra. Antifungal screening of the title compounds against ten fungi has been done and their comparative findings have been reported. The compound possessing chloro group at p-position show maximum inhibition (99.1%) against Colletotrichum sp. at 500 μg/mL concentration. The compounds possessing a methyl or chloro group at p-position also have potent anti-inflammatory and antitumor properties as they downregulate the NF-κB transcription factor.