Synthesis of 2,5-Disubstituted-1,4-benzoquinone Derivatives as Potential Antimicrobial and Cytotoxic Agents

Abstract

A number of 2,5‐disubstituted‐1,4‐benzoquinone derivatives were prepared and characterized by elemental analysis, infrared (IR), nuclear magnetic resonance (1H‐NMR), and mass spectra (MS). These compounds and their synthetic precursors were evaluated for their in vitro antimicrobial and cytotoxic activity. The most potent antimicrobial compound was the thiadiazolyl derivative 4b, which was 2‐ to 4 times more active than the antimicrobial drug sulfathiazole. All the tested compounds were active in the Brine Shrimp Lethality (BS) Test. Compound 4e which was the most active in the BS test was also found to possess a significant cytotoxicity against two tumor cell lines. Some of the compounds were found to be mutagenic at relatively high concentration.

Synthesis of Some Thiazolidine Derivatives of 1,4-Benzoquinone as Potential Antimicrobial Agents

“…2,3 Within a program aimed at developing new medicinal agents related to 1,4-benzoquinone derivatives, some pyrazolyl, oxadiazolyl or thiadiazolyl derivatives of 1,4-benzoquinone were synthesized in our laboratory and evaluated for their antimicrobial effects. [4][5][6][7] Moreover, thiazolidine derivatives have been reported to exhibit antimicrobial activity. 8 In addition and as a continuation of our continuous related program, 1,4-benzoquinone derivatives were synthesized having within their structure the thiazolidine function attached to position 2 through a carbonyl linker and 4-substituted anilino moiety attached to position 5, in order to investigate the effect of the thiazolidine moiety on the antimicrobial activity of the 1,4benzoquinone derivatives.…”