Synthesis of 1,2,3,4-tetrahydro-.BETA.-carboline derivatives as hepatoprotective agents. II. Alkyl 1,2,3,4-tetrahydro-.BETA.-carboline-2-carbodithioates.

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Abstract
A large number of alkyl 1,2,3,4-tetrahydro-.beta.-carboline-2-carbodithioates (2 and 5) with 3-hydroxycarbonyl and 3-hydroxymethyl groups were synthesized and tested for hepatoprotective activity against CCl4-induced liver damage in mice. Structure-activity relationships were investigated. Lengthening of the alkyl group in 2 and 5 tends to adversely affect the activity. Both enantiomers of the methyl derivatives (2a and 5a), the most potent compounds in this series, were synthesized, and no difference in hepatoprotective activity was observed. Apparent neighboring group participation was observed in the treatment of 5a with base or acid, giving the cyclized product (6) or the rearranged products (7, 8, and 9).