Synthesis of 14-membered enediyne-embedded macrocycles
A concise and practical strategy towards a novel class of 14-membered macrocycles containing an enediyne ( Z -3-ene-1,5-diyne) structural unit is described. A highly modular assembly of various precursors via sequential Ugi/Sonogashira reactions allowed the preparation of hybrid enediyne-peptide mac...
Saved in:
Published in | Organic & biomolecular chemistry Vol. 2; no. 18; pp. 3823 - 3834 |
---|---|
Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
England
Royal Society of Chemistry
11.05.2022
|
Subjects | |
Online Access | Get full text |
Cover
Loading…
Summary: | A concise and practical strategy towards a novel class of 14-membered macrocycles containing an enediyne (
Z
-3-ene-1,5-diyne) structural unit is described. A highly modular assembly of various precursors
via
sequential Ugi/Sonogashira reactions allowed the preparation of hybrid enediyne-peptide macrocycles in most cases as single diastereoisomers. Selected macrocyclic compounds showed moderate antiproliferative activity, and can be considered as templates suitable for further diversification in terms of ring size, shape, and stereochemistry.
Macrocyclization of precursors obtained by a sequential Ugi/Sonogashira reaction afforded a new class of 14-membered macrocycles containing an enediyne structural unit. |
---|---|
Bibliography: | For ESI and crystallographic data in CIF or other electronic format see DOI 1967883 https://doi.org/10.1039/d2ob00090c 1967885 Electronic supplementary information (ESI) available: NMR spectra, HPLC chromatograms, X-ray data, and evaluation of antiproliferative activity. CCDC and ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 1477-0520 1477-0539 |
DOI: | 10.1039/d2ob00090c |