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...

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Published inOrganic & biomolecular chemistry Vol. 2; no. 18; pp. 3823 - 3834
Main Authors Glavaš, Mladena, Gredi ak, Matija, Štefani, Zoran, Jeri, Ivanka
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 11.05.2022
Subjects
Diastereoisomers
Enediynes
Macrocyclic compounds
Stereochemistry
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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
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ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob00090c