Synthesis of tryptoline-3-carboxylic Acid derivatives a novel antidiabetic agent.

The compounds, 2-(methylsulfonyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylic acid (DM3), 2-(phenylsulfonyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylic acid (DM(4)), and 2-(p-toluenesulfonyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylic acid (DM(5)) were synthesized by coupling of 1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylic acid (DM(2)) with methanesulfonyl chloride, benzenesulfonyl chloride, and toluenesulfonyl chloride, which in turn, was synthesized by dissolving dilute aqueous ammonia with 2-(N-hydroxy methyl amino)-indol-3-yl-propanoic acid (DM(1)) which is the reaction product of l-tryptophan and formalin. All the intermediates and title compounds were characterized by physical, chemical, analytical, and spectral data. All the title compounds have been screened for in vivo antidiabetic activity in streptozotocin-induced diabetic rats, and serum glucose was estimated spectrophotometrically at 505 nm by glucose oxidase/peroxidase method. Compound DM(5) showed potent antidiabetic activity.