Synthesis of 1,2,3,4-tetrahydro-.BETA.-carboline derivatives as hepatoprotective agents. I. Dithiocarbamates of several .ALPHA.-amino acids.

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Abstract
A series of dithiocarbamates of .alpha.-amino acids was synthesized and tested for hepatoprotective activity against CCl4-induced liver damage in mice. Reaction of the amino acids (2, 4, 6 and 8) with carbon disulfide followed by methylation gave the corresponding dithiocarbamates. Among the compounds synthesized, the .beta.-carboline derivative (9a) exhibited remarkable hepatoprotective activity. The oxa analogues (9b-d) with respect to the dithiocarbamate group of 9a were also prepared. The activity of 9a-d decreased in the following order: dithiocarbamate (9a) > S-methylthiocarbamate (9b) > O-methyl thiocarbamate (9c) > carbamate (9d). The structure-activity relationships are discussed.