Antifungal properties of 2-bromo-3-fluorosuccinic acid esters and related compounds

Abstract

Twelve esters (C1-C6) of erythro- and threo-2-bromo-3-fluorosuccinic acid and related compounds were tested for antifungal activity against Candida albicans, Aspergillus niger, Mucor mucedo, and Trichophyton mentagrophytes at pH 5.7 and 7.0 in the absence and presence of 10% beef serum in Sabouraud dextrose agar. At pH 7.0 in the presence of 10% beef serum, no consistent pattern in the fungitoxicity of the erythro- and threo-2-bromo-3-fluorosuccinate esters was seen. Increasing the length of the ester function affects fungitoxicity as follows: C2 greater than C1 greater than C3 greater than C4 greater than C5 greater than C6. The most fungitoxic compound in this study was threo-ethyl 2-bromo-3-fluorosuccinate (C. albicans, 14 mug/ml; A. niger, 30 mug/ml; M. mucedo, 9 mug/ml; T. mentagrophytes, 5 mug/ml). Due to the ease of dehydrohalogenation, the fungitoxicity of 2-bromo-3-fluorosuccinic acid esters may be the result of a mixture composed of the parent compound, the bromo- and fluorofumaric acid esters, and HF and HBr of which part may be formed extracellularly and part within the cell.

Tetrabutylammonium and polymer-supported dihydrogentrifluoride: new hydrofluorinating reagents for electrophilic alkynes

“…Bun4N+H2F3-and P+H2F3-react smoothly at moderate temperatures with bis-activated A-CX-A or mono-activated R-GC-A acetylenic bonds, generating the desired addition of HF according to equation (1). In all cases the reaction stops at the alkene stage; generally a mixture of the 2and E-isomers of the fluoro-adduct A-CF=CH-A or R-CF=CH-A is obtained in good yields, a bigger proportion of syn-adduct being formed fram the polymer-supported reagent.…”

Bromofluorination of olefins using BrF3; an efficient route for fluoroalkenes and fluoroamines

“…Even more strongly deactivated olefins such as ethyl fumarate (1g), reacted successfully and ethyl 2-bromo-3-fluorosuccinate (2g) was obtained in 50% yield. The importance of this compound can be found in several papers which revealed that 2g possesses high antifungal activity due to the ease of dehydrohalogenation [19].…”

Synthesis of some substituted furan-2(5H)-ones and derived quinoxalinones as potential anti-microbial and anti-cancer agents

“…The bioactivity was shown to be associated with the ability of this group to alkylate biologically active Since microbial diseases especially those caused by fungi constitute a wide spread problem in cancer patients (Gershon and Shanks, 1977), the use of anti-microbial, anti-neoplastic drug will be advantageous. Due to an interest in developing agents in this area, some of the synthesized compounds were also screened for in vitro anti-microbial activity.…”