Antifungal Thiosulfonates: Potency with Some Selectivity

Abstract

A series of thiosulfonates have been prepared and tested against Aspergillus niger and Aspergillus flavus. In general, the thiosulfonates are moderate antifungal agents—more potent than corresponding inactive disulfides and less potent than corresponding very active fungitoxic disulfides. Apair of thiosulfonates show high selectivity, each killing only one kind of fungus.

Synthesis, characterization and antifungal testing of 3,4-dihydropyrimidin-2(1H)-(thio)ones containing boronic acids and boronate esters

“…We have examined compounds 1-5 for their ability to act as antifungal agents, using Amphotericin B as a control [30]. Although related N 2 B heterocycles are potent antifungal agents [31], none of the boron containing dihydropyrimidinones showed any appreciable activity against Aspergillus niger, Aspergillus flavus, Candida albicans and Saccharomyces cerevisiae using Amphotericin B as a control.…”

Optimizing disulfide fungitoxicity: Adjustment of hydrocarbon chain length

“…Because a very modest selection of such salts is commercially available, it soon became necessary to prepare new sulfinic acid salts. Based on our earlier unpublished results, we applied reactions between sulfonyl chlorides and sodium thiophenolate to the development of a new synthesis of sodium sulfinate salts [6] (see Sch. 2).…”

“…Recently, we have established that three types of disulfides have significant fungitoxicity: a-sulfone disulfides [1][2][3], some substituted aryl disulfides [4] and a-ester disulfides in which the ester moiety is attached to the disulfide framework by a CO bond [1,3,5]. In contrast, related thiosulfonates had only modest fungitoxicity [6].…”

“…In contrast, related thiosulfonates had only modest fungitoxicity [6]. Routine testing employed Aspergillus niger and Aspergillus flavus.…”

Synthesis, structure, and antifungal activity of dihydropyridones containing boronate esters

“…Initial studies were carried out using four fungi, Aspergillus niger, A. flavus, Candida albicans, and Saccharomyces cerevisiae, employing Amphotericin B (AmB) as a control [12,[33][34][35]. Although compounds 2a and 2b both showed appreciable activity (Table 1), the para derivative 2c was inactive (not shown).…”