Synthesis of 1, 2, 3, 4-Tetrahydro-β-carboline Derivatives as Hepatoprotective Agents. III. Introduction of Substituents onto Methyl 1, 2, 3, 4-Tetrahydro-β-carboline-2-carbodithioate

YUTAKA SAIGA; IKUO IIJIMA; AKIHIKO ISHIDA; TOSHIKAZU MIYAGISHIMA; KOICHI HOMMA; TOKURO OH-ISHI; MAMORU MATSUMOTO; YUZO MATSUOKA

doi:10.1248/cpb.35.3284

YUTAKA SAIGA, IKUO IIJIMA, AKIHIKO ISHIDA, TOSHIKAZU MIYAGISHIMA, KOICHI HOMMA, TOKURO OH-ISHI, MAMORU MATSUMOTO, YUZO MATSUOKA

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Keywords: dithiocarbamate, substituted tetrahydro-β-carboline, hepatoprotective activity, carbon tetrachloride-induced liver damage, structure-activity relationship, neighboring group participation

JOURNAL FREE ACCESS

1987 Volume 35 Issue 8 Pages 3284-3291

DOI https://doi.org/10.1248/cpb.35.3284

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Abstract

Dithiocarbamates of various substituted tetrahydro-β-carbolines were synthesized and tested for hepatoprotective activity against carbon tetrachloride (CCl₄) -induced liver damage in mice. Structure-activity relationships were investigated. Some neighboring group participation of the 3-substituent with the dithiocarbamate group appeared to be important for the manifestation of activity. The compounds (1a, 2a, and 3i) with hydrophilic substituents at the 3 poisition exhibited significant activity. Substitution at the 9 position of the 3-carboxylic acid (1a) lowered the activity.

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