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Synthesis of 14-membered enediyne-embedded macrocycles. 2022

Mladena Glavaš, and Matija Gredičak, and Zoran Štefanić, and Ivanka Jerić
Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička c. 54, 10000 Zagreb, Croatia. ivanka.jeric@irb.hr.

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.

UI MeSH Term Description Entries
D010455 Peptides Members of the class of compounds composed of AMINO ACIDS joined together by peptide bonds between adjacent amino acids into linear, branched or cyclical structures. OLIGOPEPTIDES are composed of approximately 2-12 amino acids. Polypeptides are composed of approximately 13 or more amino acids. PROTEINS are considered to be larger versions of peptides that can form into complex structures such as ENZYMES and RECEPTORS. Peptide,Polypeptide,Polypeptides
D047028 Macrocyclic Compounds Cyclic compounds with a ring size of approximately 1-4 dozen atoms. Macrocycle Compounds,Spherands,Torands,Compounds, Macrocycle,Compounds, Macrocyclic
D053281 Enediynes Compounds with triple bonds to each side of a double bond. Many of these are CYTOTOXINS and are researched for use as CYTOTOXIC ANTIBIOTICS. Enediyne Group

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