Add time:09/05/2019 Source:sciencedirect.com
An efficient protocol for highly chemoselective introduction of dithiocarbamate groups to nitrogen position of indoles with bis(dialkylaminethiocarbonyl)disulfides was achieved by employing t-BuOK as a promoter. Based on this methodology, twenty nine novel indole-dithiocarbamate compounds were prepared in moderate to excellent yields at room temperature. All compounds were evaluated for their anti-inflammatory activity. Most of the compounds exhibited high potency on inhibiting the releasing of tumor necrosis factor alpha (TNF-α) and interleukin-6 (IL-6). Four of them were found to suppress in vitro cytokine production in a dose-dependent manner with IC50 values in the nanomolar range. Additionally, 3-methyl-1H-indol-1-yl dimethylcarbamodithioate (3o) effectively ameliorated histopathological changes of lung tissues and attenuated lipopolysaccharides (LPS)-induced acute lung injury (ALI) in vivo. These data suggest that the new indole-dithiocarbamate derivatives could be particularly useful for further pharmaceutical development for the treatment of ALI.
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