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 <b style="">4a-e </b>have been synthesized by oxidative debenzylation and cyclization with bromine in chloroform from the corresponding 1-substituedaryl-5-(2,4-diethoxyaryl)-2-<i style="">S</i>-benzyl-<i style="">iso</i>-2,4-dithiobiurets <b style="">3a-e</b> or by the oxidation of corresponding 1-substituted aryl-5-(2,4-diethoxyaryl)-2,4-dithio­biurets <b style="">5a-e,</b> obtained from <b style="">3 a-e</b> by reductive debenzylation with hydrogen sulphide in a mixture of pyridine and triethylamine.1-Substituted aryl-5-(2,4-diethoxyaryl)-2-<i style="">S</i>-benzyl-<i style="">iso</i>-2,4-dithiobiurets <b style="">3a-e</b>, in turn, are prepared by the condensation of 1-substituted aryl-2-<i style="">S</i>-benzylisocarbamides <b style="">2a-e</b> 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 <i style="">p</i>-position show maximum inhibition (99.1%) against <i style="">Colletotrichum </i>sp. at 500 <img src='/image/spc_char/micro.gif' border=0>g/mL concentration. The compounds possessing a methyl or chloro group at <i style="">p</i>-position also have potent anti-inflammatory and antitumor properties as they downregulate the NF- kB transcription factor.