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

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,...

Descripción completa

Detalles Bibliográficos
Autores principales: Byeon, Hong-Ju, Jung, Kyung-Hwan, Moon, Gi-Seong, Moon, Sung-Kwon, Lee, Hyang-Yeol
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2020
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6978303/
https://www.ncbi.nlm.nih.gov/pubmed/31974432
http://dx.doi.org/10.1038/s41598-020-57911-0
_version_ 1783490668732088320
author Byeon, Hong-Ju
Jung, Kyung-Hwan
Moon, Gi-Seong
Moon, Sung-Kwon
Lee, Hyang-Yeol
author_facet Byeon, Hong-Ju
Jung, Kyung-Hwan
Moon, Gi-Seong
Moon, Sung-Kwon
Lee, Hyang-Yeol
author_sort Byeon, Hong-Ju
collection PubMed
description 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.
format Online
Article
Text
id pubmed-6978303
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher Nature Publishing Group UK
record_format MEDLINE/PubMed
spelling pubmed-69783032020-01-29 A facile and efficient method for the synthesis of crystalline tetrahydro-β-carbolines via the Pictet-Spengler reaction in water Byeon, Hong-Ju Jung, Kyung-Hwan Moon, Gi-Seong Moon, Sung-Kwon Lee, Hyang-Yeol Sci Rep Article 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. Nature Publishing Group UK 2020-01-23 /pmc/articles/PMC6978303/ /pubmed/31974432 http://dx.doi.org/10.1038/s41598-020-57911-0 Text en © The Author(s) 2020 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
Byeon, Hong-Ju
Jung, Kyung-Hwan
Moon, Gi-Seong
Moon, Sung-Kwon
Lee, Hyang-Yeol
A facile and efficient method for the synthesis of crystalline tetrahydro-β-carbolines via the Pictet-Spengler reaction in water
title A facile and efficient method for the synthesis of crystalline tetrahydro-β-carbolines via the Pictet-Spengler reaction in water
title_full A facile and efficient method for the synthesis of crystalline tetrahydro-β-carbolines via the Pictet-Spengler reaction in water
title_fullStr A facile and efficient method for the synthesis of crystalline tetrahydro-β-carbolines via the Pictet-Spengler reaction in water
title_full_unstemmed A facile and efficient method for the synthesis of crystalline tetrahydro-β-carbolines via the Pictet-Spengler reaction in water
title_short A facile and efficient method for the synthesis of crystalline tetrahydro-β-carbolines via the Pictet-Spengler reaction in water
title_sort facile and efficient method for the synthesis of crystalline tetrahydro-β-carbolines via the pictet-spengler reaction in water
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6978303/
https://www.ncbi.nlm.nih.gov/pubmed/31974432
http://dx.doi.org/10.1038/s41598-020-57911-0
work_keys_str_mv AT byeonhongju afacileandefficientmethodforthesynthesisofcrystallinetetrahydrobcarbolinesviathepictetspenglerreactioninwater
AT jungkyunghwan afacileandefficientmethodforthesynthesisofcrystallinetetrahydrobcarbolinesviathepictetspenglerreactioninwater
AT moongiseong afacileandefficientmethodforthesynthesisofcrystallinetetrahydrobcarbolinesviathepictetspenglerreactioninwater
AT moonsungkwon afacileandefficientmethodforthesynthesisofcrystallinetetrahydrobcarbolinesviathepictetspenglerreactioninwater
AT leehyangyeol afacileandefficientmethodforthesynthesisofcrystallinetetrahydrobcarbolinesviathepictetspenglerreactioninwater
AT byeonhongju facileandefficientmethodforthesynthesisofcrystallinetetrahydrobcarbolinesviathepictetspenglerreactioninwater
AT jungkyunghwan facileandefficientmethodforthesynthesisofcrystallinetetrahydrobcarbolinesviathepictetspenglerreactioninwater
AT moongiseong facileandefficientmethodforthesynthesisofcrystallinetetrahydrobcarbolinesviathepictetspenglerreactioninwater
AT moonsungkwon facileandefficientmethodforthesynthesisofcrystallinetetrahydrobcarbolinesviathepictetspenglerreactioninwater
AT leehyangyeol facileandefficientmethodforthesynthesisofcrystallinetetrahydrobcarbolinesviathepictetspenglerreactioninwater

Ejemplares similares