A facile and efficient method for the synthesis of crystalline tetrahydro-β-carbolines via the Pictet-Spengler reaction in water
Hong-Ju Byeon, Kyung‐Hwan Jung, Gi‐Seong Moon, Sung‐Kwon Moon, Hyang‐Yeol Lee
Abstract
Abstract A facile and efficient synthesis of tetrahydro-β-carbolines (tryptolines) in one step from tryptamine and aldehydes, in an environmentally friendly water solvent, has been investigated. This convenient and clean synthesis of various tryptolines was facilitated by l -tartaric acid, a natural compound, to obtain the desired products as clear crystals. Among the four crystalline products, the most substituted tryptoline 2 showed the best inhibitory activity against EJ cells and the least cytotoxicity, with an LC 50 value of 1.49 mg/mL, against brine shrimp larvae.
Topics & Concepts
Pictet–Spengler reactionComputer scienceChemistryCombinatorial chemistryOrganic chemistrySynthesis and bioactivity of alkaloidsMulticomponent Synthesis of HeterocyclesSynthesis of Indole Derivatives