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An Indole Dearomatization Strategy for the Synthesis of Pseudo‐Natural Products
Author(s) -
Hoock Joseph G. F.,
Burhop Annina,
Greiner Luca C.,
Schölermann Beate,
Da Cruz Lopes Guita Celine,
Liu Jie,
Bag Sukdev,
Pahl Axel,
Sievers Sonja,
Scheel Rebecca,
Strohmann Carsten,
Ziegler Slava,
Grigalunas Michael,
Waldmann Herbert
Publication year - 2025
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.202500182
The indole moiety is a privileged fragment that frequently populates existing bioactive compound collections. The development of an indole‐dearomatization sequence and its application for library expansion of a collection of indole‐containing pseudo‐natural products (NPs) are described. The resulting compounds are topologically distinct from the original compound class. Phenotyping by means of the cell painting assay initially indicates that the dearomatized compounds are morphologically different than the original pseudo‐NP compound class and guiding NPs. However, analysis by means of a new subprofile analysis of the same cell painting assay data indicates that similar morphologies persist throughout the compound classes. Further biological studies support the findings of the subprofile analysis and highlight its potential to more effectively characterize novel compounds. The biological findings suggest that a plethora of indole‐dearomatization reactions can be applied to existing indole‐containing compound collections to rapidly access new biologically relevant scaffolds.

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