Naslov
Synthesis of enediyne peptidomimetics by Passerini reaction

Autori
Glavaš, Mladena ; Gredičak, Matija ; Jerić, Ivanka

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
25. Hrvatski skup kemičara i kemijskih inženjera s međunarodnim sudjelovanjem ; 3. simpozij Vladimir Prelog : knjiga sažetaka = 25th Croatian Meeting of Chemist and Chemical Engineers with international participation. 3rd symposium “Vladimir Prelog” : Book of Abstracts / Šantić, Ana ; Đaković, Marijana - Zagreb : Hrvatsko društvo kemijskih inženjera i tehnologa (HDKI) ; Hrvatsko kemijsko drustvo, 2017, 134-134

ISBN
978-953-552327-7

Skup
25. Hrvatski skup kemičara i kemijskih inženjera s međunarodnim sudjelovanjem ; 3. simpozij Vladimir Prelog = 25th Croatian Meeting of Chemist and Chemical Engineers with international participation. 3rd symposium “Vladimir Prelog”

Mjesto i datum
Poreč, Hrvatska, 19.04.2017. - 22.04.2017

Vrsta sudjelovanja
Poster

Vrsta recenzije
Domaća recenzija

Ključne riječi
multicomponent reactions ; Passerini reaction ; enediynes

Sažetak
A significant area of organic chemistry is chemical synthesis performed through one–pot mode. [1] Such reactions, known as multicomponent reactions comprise three or more starting reagents and give a single product. The main advantage of multicomponent reactions are an easy access to libraries of complex and structurally diverse compounds starting from relatively simple components. Isocyanide–based multicomponent reactions, e.g. Passerini and Ugi reactions are of special importance, because they provide diverse peptide-like compounds. The Passerini reaction is one of the oldest multicomponent reaction used for the construction of α- acyloxyamides–depsipeptides. The reaction involves coupling of aldehyde, carboxylic acid and isocyanide in a nonpolar solvent. [2] We are interested in utilizing multicomponent reactions for the synthesis of conformationally constrained peptidomimetics. The enediyne structural motif (Figure 1) found in natural products with strong anticancer activity [3] was shown to induce β-turn or β-sheet conformation when incorporated into peptides. Therefore, we decided to use the Passerini reaction for the synthesis of a new class of enediyne-based depsipeptides. Enediyne aldehyde 1, prepared by two consecutive Sonogashira reactions, was coupled with different isocyanides and carboxylic acid in dichloromethane on room temperature (Figure 1). Enediyne depsipeptides 2 were obtained in up to 92 % yields.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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