Synthesis of 1,2,3,4-Tetrahydro-β-carboline Derivatives as Hepatoprotective Agents. IV. : Positional Isomers of 1,2,3,4-Tetrahydro-2-methylthiothiocarbonyl-β-carboline-3-carboxylic Acid and Its 1-Alkylated Derivatives(Medeicinal Chemistry,Chemical)

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Two tetrahydro-β-carboline-1- and -4-carboxylic acids (1b, c) and the corresponding hydroxymethyl derivatives (2b, c), which are positional isomers of the 3-carboxylic acid (1a) and its 3-hydroxymethyl derivative (2a), were synthesized and tested for hepatoprotective activity against carbon tetrachloride (CCl_4)-induced liver damage in mice. The hepatoprotective activity of these positional isomers decreased in the following order; 1a>1b>1c> and 2a>2b>2c. The effect of alkyl substitution at the 1 position of 1a and 2a was also examined with the cis and trans isomers (5a, b-14a, b). Compounds with small alkyl groups such as Me and Et showed potent activity. Lengthening of the alkyl group generally caused a decrease in activity. In a series of the stereoisomers of the 3-carboxylic acids (5a, b-9a, b), the cis isomers tend to be more active than the trans counterparts.
公益社団法人日本薬学会の論文
1987-09-25