Syntheses and complement inhibitory activities of 4-(2-phenyl-1H-indol-3-yl)cyclohexane-1-carboxylic acids

Abstract
The syntheses of 4-(2-phenyl-1H-indol-3-yl)cyclohexane-1-carboxylic acids [4-(2-phenyl-1H-indol-3-yl)-3-cyclohexene-1-carboxylic acid, 4-(2-phenyl-1H-indol-3-yl)-3-cyclohexene-1,1-dicarboxylic acid, 4-(1-methyl-2-phenyl-1H-indol-3-yl)-3-cyclohexene-1,1-dicarboxylic acid, 4-(1-methyl-2-phenyl-1H-indol-3-yl)-3-cyclohexane-1-carboxylic acid, 4-(1-ethyl-2-phenyl-1H-indol-3-yl)-3-cyclohexene-1-carboxylic acid, 4-(2-phenyl-1-propyl-1H-indol-3-yl)-3-cyclohexene-1-carboxylic acid, 4-(1-ethyl-2-phenyl-1H-indol-3-yl)-3-cyclohexene-1,1-dicarboxylic acid, 4-(2-phenyl-1H-indol-3-yl)cyclohexane-1,1-dicarboxylic acid, 4-(1-methyl-2-phenyl-1H-indol-3-yl)cyclohexane-1,1-dicarboxylic acid, cis-trans-4-(1-methyl-2-phenyl-1H-indol-3-yl)cyclohexane-1-carboxylic acid, cis-4-(1-methyl-2-phenyl-1H-indol-3-yl)-1,1-cyclohexane dicarboxylic acid, 4-(2-phenyl-1H-indol-3-yl)benzoic acid and 4-(1-methyl-2-phenyl-1H-indol-3-yl)benzoic acid] are described. These compounds expressed potent in vitro inhibition of the human classical complement pathway, and qualitative SAR [structure-activity relationship] was determined. Several of the in vitro compounds also suppressed the complement dependent reverse passive Arthus reactin (RPAR) in guinea pigs.

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