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A facile and efficient method for the synthesis of crystalline tetrahydro-?-carbolines via the Pictet-Spengler reaction in water.

ABSTRACT: A facile and efficient synthesis of tetrahydro-?-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 LC50 value of 1.49?mg/mL, against brine shrimp larvae.

SUBMITTER: Byeon HJ

PROVIDER: S-EPMC6978303 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

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A facile and efficient method for the synthesis of crystalline tetrahydro-β-carbolines via the Pictet-Spengler reaction in water.

Byeon Hong-Ju HJ Jung Kyung-Hwan KH Moon Gi-Seong GS Moon Sung-Kwon SK Lee Hyang-Yeol HY

Scientific reports 20200123 1

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 cytotoxicit ...[more]

PMID: 31974432

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