Precursor‐Directed Synthesis of Apoptosis‐Initiating N‐Hydroxyalkyl Phenylbenzoisoquinolindione Alkaloids

A precursor‐directed approach to access N‐hydroxyalkyl phenylbenzoisoquinolindiones (PBIQs) has been developed. Incubation of plant material of Xiphidium caeruleum with hydroxylamines of various chain lengths (C(2), C(4), C(6), C(8), C(10) and C(12)) resulted in 11 new 5‐hydroxy‐ and 5‐methoxy PBIQs...

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Detalles Bibliográficos
Autores principales: Chen, Yu, Dahse, Hans‐Martin, Paetz, Christian, Schneider, Bernd
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Research Articles
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9728486/
https://www.ncbi.nlm.nih.gov/pubmed/36478420
http://dx.doi.org/10.1002/open.202200157
Descripción
Sumario:A precursor‐directed approach to access N‐hydroxyalkyl phenylbenzoisoquinolindiones (PBIQs) has been developed. Incubation of plant material of Xiphidium caeruleum with hydroxylamines of various chain lengths (C(2), C(4), C(6), C(8), C(10) and C(12)) resulted in 11 new 5‐hydroxy‐ and 5‐methoxy PBIQs with different N‐hydroxyalkyl side chain lengths. The antiproliferative effect and the cytotoxicity against HUVEC, K‐562, and HeLa cell lines of 26 previously reported PBIQs and the 11 newly synthesized N‐hydroxyalkyl PBIQs was determined for the first time. The results revealed that introducing long‐chain N‐aliphatic amine moieties improved the antiproliferative effect and cytotoxicity of PBIQs when compared to derivatives with N‐amino acids as side chains.

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